Biofouling resistant coatings and methods of making and using same - Patents.com

Abstract

Disclosed herein are compositions for use in biofouling resistant coatings, biofouling resistant coatings, methods of making biofouling resistant coatings, biofouling resistant devices, and methods of making biofouling resistant devices.

Description

[Technical field]

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS This application claims the benefit of U.S. Provisional Patent Application No. 62 / 857,725, filed June 5, 2019, the contents of which are incorporated by reference in their entirety herein. [Background technology]

[0002] Hospital-acquired infections (HAIs) are responsible for over 100,000 deaths and over $30 billion in direct health care costs annually. In some cases, medical devices implanted in the body are the source of HAIs. Planktonic bacteria attach to the surface of the medical device and begin to grow into an elastic biofilm that becomes more resistant to antibiotics and disinfectants than when in a planktonic state. Summary of the Invention [Means for solving the problem]

[0003] In certain embodiments, described herein are compositions for use in biofouling resistant coatings, biofouling resistant coatings, methods of making biofouling resistant coatings, biofouling resistant devices, and methods of making biofouling resistant devices.

[0004] In one aspect, a compound of formula (I) is described herein: [ka] During the ceremony, A is -C(=O)-, -S(=O)-, -S(=O) 2 - and -S(=O)(-NR 3 )- is selected from L is -OQ, -NR 3 Q, and -N(R 3 ) 2 Q + is selected from Q is a structure represented by the following formula: [ka] Z is -CR 6a R 6b -, -C(=O)-, -C(=NH)-, and -C(=NH)NR 7 - selected from m is an integer selected from 0, 1, 2, 3, 4, 5, 6, 7, and 8; Each R 1a and R 1b is independently selected from hydrogen and halogen; Each R 2a and R 2b are independently selected from halogen, -CN, and optionally substituted C 1 -C 6 fluoroalkyl; Each R 3 are independently hydrogen, optionally substituted C 1 -C 4 Alkyl, -X-optionally substituted C 1 -C 4 selected from alkyl, optionally substituted aryl, and -X-optionally substituted aryl; X is -C(=O)-, -S(=O)-, or -S(=O) 2 - and Each R 4a , R 4b , R 5a , R 5c , R 6a , and R 6b are independently hydrogen, halogen, -CN, -OH, optionally substituted C 1 -C 4 Alkyl, optionally substituted C 1 -C 4 Fluoroalkyl, optionally substituted aryl, -NR 8a R 8b , -NR 8a R 8b R 8c+ , -S(=O) 2 O - , -S(=O) 2 OR 9 , -C(=O)O - , and -C(=O)OR9 is selected from R 5b -OR 10b , -NR 10a R 10b , or -NR 10a R 10b R 10c+ and Each R 7 , R 8a , R 8b , R 8c , and R 9 are independently hydrogen and optionally substituted C 1 -C 4 selected from alkyl and optionally substituted aryl; Each R 10a and R 10c are independently hydrogen, optionally substituted C 1 -C 4 Alkyl, optionally substituted aryl, -(optionally substituted C 1 -C 8 Alkylene)S(=O) 2 O - , -(optionally substituted C 1 -C 8 Alkylene)S(=O) 2 OH, -(optionally substituted C 1 -C 8 Alkylene)C(=O)O - , and -(optionally substituted C 1 -C 8 alkylene)C(=O)OH; R 10b is -C(=O)-C 2 -C 6 Alkenyl, -S(=O)-C 2 -C 6 Alkenyl, or -S(=O) 2 -C 2 -C 6 Although it is alkenyl, With the proviso that the compound of formula (I) is N-(2-((4-azido-2,3,5,6-tetrafluorophenyl)sulfonamido)ethyl)methacrylamide, N-(2-acrylamidoethyl)-4-azido-2,3,5,6-tetrafluorobenzamide, or Provided that it is not 2-(methacryloyloxy)ethyl 4-azido-2,3,5,6-tetrafluorobenzoate.

[0005] In another aspect, there is provided a compound of formula (II) as described herein: [ka] During the ceremony, Each R 1a and R 1b is independently selected from hydrogen and halogen; Each R 2a and R 2b are independently selected from halogen, -CN, and optionally substituted C 1 -C 6 fluoroalkyl; Each A 1 , A 2 , and A 3 are independently -C(=O)-, -S(=O)-, -S(=O) 2 - and -S(=O)(=NR 3c )- is selected from Each B 1 , B 2 , and B. 3 are independently -O- and -NR 3c - selected from D is -S(=O) 2 O - , -S(=O) 2 OR 9a , -C(=O)O - , or -C(=O)OR 9a and Z 1 is -(CR 6c R 6d ) s - and Z 2 is -(CR 6c R 6d ) t - and Z 3is -(CR 6c R 6d ) p - and Each R 3a and R 3b are independently hydrogen, optionally substituted C 1 -C 4 alkyl, and optionally substituted benzyl; Each R 4c , R 4d , R 5d , R 5e , R 6c , and R 6d are independently hydrogen, halogen, -CN, -OH, optionally substituted C 1 -C 4 Alkyl, optionally substituted C 1 -C 4 Fluoroalkyl, optionally substituted C 2 -C 6 Alkenyl, -NR 3c R 3d , -S(=O) 2 O - , -S(=O) 2 OR 9a , -C(=O)O - , and -C(=O)OR 9a is selected from Each R 3c and R 3d are independently hydrogen, optionally substituted C 1 -C 4 Alkyl, -X-optionally substituted C 1 -C 4 Alkyl, optionally substituted C 2 -C 6 alkenyl, and optionally substituted aryl; X is -C(=O)-, -S(=O)-, or -S(=O) 2 - and Each R 9a , R 11a , R 11b , R 11c , R 12a , R 12b , and R 12care independently hydrogen, optionally substituted C 1 -C 4 alkyl, and optionally substituted aryl; n is an integer selected from 0, 1, 2, 3, 4, 5, 6, 7, and 8; s is an integer selected from 1, 2, 3, 4, or 5; t is an integer selected from 1, 2, 3, 4, or 5; p is an integer selected from 1, 2, 3, 4, or 5; x is 0.001 to 0.999, The compounds of formula (II) are charged or zwitterionic, However, the compound of formula (II) [ka] The condition is that it is not.

[0006] In another aspect, there is provided a compound of formula (III) as described herein: [ka] During the ceremony, Each R 1a and R 1b is independently selected from hydrogen and halogen; Each R 2a and R 2b are independently selected from halogen, -CN, and optionally substituted C 1 -C 6 fluoroalkyl; Each A 1 , A 2 , and A 3 are independently -C(=O)-, -S(=O)-, -S(=O) 2 - and -S(=O)(=NR 3c )- is selected from Each B 1 , B 2 , and B. 3 are independently -O- and -NR 3c - selected from Z 1 is -(CR 6c R 6d ) s - and Z 2 is -(CR 6c R 6d ) t - and E is -CN, -OR 9a , -NR 9a R 9b , -NR 9a R 9b R 9c+ , optionally substituted C 1 -C 4 Alkyl, optionally substituted C 1 -C 6 Fluoroalkyl, -S(=O) 2 O - , -S(=O) 2 OR 9a , -C(=O)O - , or -C(=O)OR 9a and Each R 4c , R 4d , R 5d , R 5e , R 6c , and R 6d are independently hydrogen, halogen, -CN, -OR 9a , optionally substituted C 1 -C 4 Alkyl, optionally substituted C 1 -C 4 Fluoroalkyl, optionally substituted C 2 -C 6 Alkenyl, -NR 3c R 3d , -S(=O) 2 O - , -S(=O) 2 OR 9a , -C(=O)O - , and -C(=O)OR 9a is selected from Each R 3c and R 3d are independently hydrogen, optionally substituted C 1 -C4 Alkyl, -X-optionally substituted C 1 -C 4 Alkyl, optionally substituted C 2 -C 6 alkenyl, and optionally substituted aryl; X is -C(=O)-, -S(=O)-, or -S(=O) 2 - and Each R 9a , R 9b , R 9c , R 11a , R 11b , R 11c , R 12a , R 12b , and R 12c are independently hydrogen, optionally substituted C 1 -C 4 alkyl, and optionally substituted aryl; n is an integer selected from 0, 1, 2, 3, 4, 5, 6, 7, and 8; s is an integer selected from 1, 2, 3, 4, or 5; t is an integer selected from 1, 2, 3, 4, or 5; x is between 0.001 and 0.999.

[0007] In another aspect, a copolymer is described herein, the copolymer comprising: a) a repeating unit of formula (VII): [ka] (In the formula, Each R 1a and R 1b is independently selected from hydrogen and halogen; Each R 2a and R 2b are independently selected from halogen, -CN, and optionally substituted C 1 -C 6 fluoroalkyl; Each A 1 and A 2are independently -C(=O)-, -S(=O)-, -S(=O) 2 - and -S(=O)(=NR 3c )- is selected from Each B 1 and B. 2 are independently -O- and -NR 3c - selected from Z 1 is -(CR 6c R 6d ) s - and Each R 4c , R 4d , R 5d , R 5e , R 6c , and R 6d are independently hydrogen, halogen, -CN, -OR 9a , optionally substituted C 1 -C 4 Alkyl, optionally substituted C 1 -C 4 Fluoroalkyl, optionally substituted C 2 -C 6 Alkenyl, -NR 3c R 3d , -S(=O) 2 O - , -S(=O) 2 OR 9a , -C(=O)O - , and -C(=O)OR 9a is selected from Each R 3c and R 3d are independently hydrogen, optionally substituted C 1 -C 4 Alkyl, -X-optionally substituted C 1 -C 4 Alkyl, optionally substituted C 2 -C 6 alkenyl, and optionally substituted aryl; X is -C(=O)-, -S(=O)-, or -S(=O) 2 - and Each R 9a , R 11a , R11b , and R 11c are independently hydrogen, optionally substituted C 1 -C 4 alkyl, and optionally substituted aryl; n is an integer selected from 0, 1, 2, 3, 4, 5, 6, 7, and 8; s is an integer selected from 1, 2, 3, 4, and 5; b) A repeating unit of formula (VIII): [ka] (In the formula, (A 3 -C(=O)-, -S(=O)-, -S(=O) 2 - or -S(=O)(=NR 3c )-and B 3 is -O- or -NR 3c - and D is -S(=O) 2 O - , -S(=O) 2 OR 9a , -C(=O)O - , or -C(=O)OR 9a and Z 2 is -(CR 6c R 6d ) t - and Z 3 is -(CR 6c R 6d ) p - and Each R 3a and R 3b are independently hydrogen, optionally substituted C 1 -C 4 alkyl, and optionally substituted benzyl; Each R 6c and R 6d are independently hydrogen, halogen, -CN, -OR 9a , optionally substituted C 1 -C 4Alkyl, optionally substituted C 1 -C 4 Fluoroalkyl, optionally substituted C 2 -C 6 Alkenyl, -NR 3c R 3d , -S(=O) 2 O - , -S(=O) 2 OR 9a , -C(=O)O - , and -C(=O)OR 9a is selected from Each R 3c and R 3d are independently hydrogen, optionally substituted C 1 -C 4 Alkyl, -X-optionally substituted C 1 -C 4 Alkyl, optionally substituted C 2 -C 6 alkenyl, and optionally substituted aryl; X is -C(=O)-, -S(=O)-, or -S(=O) 2 - and Each R 9a , R 12a , R 12b , and R 12c are independently hydrogen, optionally substituted C 1 -C 4 alkyl, and optionally substituted aryl; t is an integer selected from 1, 2, 3, 4, or 5; p is an integer selected from 1, 2, 3, 4, or 5; A repeat unit of formula (VIII), wherein the repeat unit of formula (VIII) is charged or zwitterionic; c) A repeating unit of formula (IX): [ka] (In the formula, A 4 -C(=O)-, -S(=O)-, -S(=O) 2- or -S(=O)(=NR 3c )-and B 4 is -O- or -NR 3c - and Z 4 is -(CR 6c R 6d ) k - and E is -CN, -OR 9a , -NR 9a R 9b , -NR 9a R 9b R 9c+ , optionally substituted C 1 -C 4 Alkyl, optionally substituted C 1 -C 6 Fluoroalkyl, -S(=O) 2 O - , -S(=O) 2 OR 9a , -C(=O)O - , or -C(=O)OR 9a and Each R 6c and R 6d are independently hydrogen, halogen, -CN, -OR 9a , optionally substituted C 1 -C 4 Alkyl, optionally substituted C 1 -C 4 Fluoroalkyl, optionally substituted C 2 -C 6 Alkenyl, -NR 3c R 3d , -S(=O) 2 O - , -S(=O) 2 OR 9a , -C(=O)O - , and -C(=O)OR 9a is selected from Each R 3c and R 3d are independently hydrogen, optionally substituted C 1 -C 4 Alkyl, -X-optionally substituted C 1 -C4 Alkyl, optionally substituted C 2 -C 6 alkenyl, and optionally substituted aryl; X is -C(=O)-, -S(=O)-, or -S(=O) 2 - and Each R 9a , R 9b , R 9c , R 13a , R 13b , and R 13c are independently hydrogen, optionally substituted C 1 -C 4 alkyl, and optionally substituted aryl; k is an integer selected from 1, 2, 3, 4, or 5.

[0008] Any combination of the groups described above or below for the various variables is contemplated herein. Throughout the specification, groups and substituents thereof are chosen by one of ordinary skill in the art to provide stable moieties and compounds.

[0009] In another aspect, described herein are medical devices coated with a compound of Formula (I), (II), or (III).

[0010] In another aspect, described herein are medical devices coated with copolymers comprising recurring units of formulas (VII), (VIII), and (IX).

[0011] In another aspect, described herein is a biofouling resistant medical device, wherein the surface of the medical device is coated with a phenyl azide-based copolymer having a number average molecular weight of about 10,000 to about 250,000.

[0012] In another aspect, described herein is a biofouling resistant medical device, wherein the surface of the medical device is coated with a phenyl azide-based copolymer having a number average molecular weight of about 14,000 to about 21,000.

[0013] In another aspect, described herein is a biofouling resistant medical device, wherein the surface of the medical device is coated with a phenyl azide-based copolymer having a polydispersity index (PDI) of about 1-1.5.

[0014] In another aspect, described herein is a method of preparing a biofouling resistant medical device, the method comprising: a) contacting a surface of a medical device with a mixture comprising a charged or zwitterionic copolymer; b) treating the surface of the medical device of step a) with a light source for a time sufficient to effect photo-grafting of a charged or zwitterionic copolymer onto the surface of the medical device, thereby producing a biofouling resistant medical device; The charged or zwitterionic copolymers include phenyl azide-based copolymers, the charged or zwitterionic copolymers having a number average molecular weight of about 10,000 to about 250,000.

[0015] In another aspect, described herein is a method of preparing a biofouling resistant medical device, the method comprising: a) contacting a surface of a medical device with a mixture (e.g., a solution) comprising a charged or zwitterionic copolymer; b) treating the surface of the medical device of step a) with a light source for a time sufficient to effect photo-grafting of a charged or zwitterionic copolymer onto the surface of the medical device, thereby producing a biofouling resistant medical device; The charged or zwitterionic copolymers include phenyl azide-based copolymers, the charged or zwitterionic copolymers having a number average molecular weight of about 14,000 to about 21,000.

[0016] In another aspect, described herein is a method of preparing a charged or zwitterionic copolymer modified biofouling resistant device, the method comprising: a) contacting a surface of a silicon-based device with a mixture (e.g., a solution) comprising a charged or zwitterionic copolymer; b) treating the surface of the device of step a) with a light source for a time sufficient to effect photo-grafting of a charged or zwitterionic copolymer onto the surface of the silicon-based device, thereby producing a charged or zwitterionic modified device; Charged or zwitterionic copolymers include phenylazide-based copolymers.

[0017] In another aspect, described herein is a method of preparing a charged or zwitterionic copolymer modified biofouling resistant device, the method comprising: a) contacting a surface of the device with a mixture (e.g., a solution) comprising a charged or zwitterionic copolymer; b) treating the surface of the device of step a) with a light source for a time sufficient to effect photo-grafting of a charged or zwitterionic copolymer onto the surface of the device, thereby producing a charged or zwitterionic modified device; The charged or zwitterionic copolymers include phenyl azide-based copolymers, the charged or zwitterionic copolymers having a number average molecular weight of about 10,000 to about 250,000.

[0018] In another aspect, described herein is a method for preparing a biofouling resistant device modified with a charged or zwitterionic copolymer, the method comprising: a) contacting a surface of the device with a mixture (e.g., a solution) comprising a charged or zwitterionic copolymer; b) treating the surface of the device of step a) with a light source for a time sufficient to effect photo-grafting of a charged or zwitterionic copolymer onto the surface of the device, thereby producing a charged or zwitterionic modified device; The charged or zwitterionic copolymers include phenyl azide-based copolymers, the charged or zwitterionic copolymers having a number average molecular weight of about 14,000 to about 21,000.

[0019] In yet another aspect, described herein is a method for synthesizing a compound of formula (II), the method comprising reacting a compound of formula (IV), or a salt or solvate thereof, with a compound of formula (V): [ka] During the ceremony, Each R 1a and R 1b is independently selected from hydrogen and halogen; Each R 2a and R 2b are independently selected from halogen, -CN, and optionally substituted C 1 -C 6 fluoroalkyl; Each A 1 , A 2 , and A 3 are independently -C(=O)-, -S(=O)-, -S(=O) 2 - and -S(=O)(=NR 3c )- is selected from Each B 1 , B 2 , and B. 3 are independently -O- and -NR 3c - selected from D is -S(=O) 2 O - , -S(=O) 2 OR 9a , -C(=O)O - , or -C(=O)OR 9a and Z 1 is -(CR 6c R 6d ) s - and Z 2 is -(CR 6c R 6d ) t - and Z 3 is -(CR 6c R 6d ) p - and Each R 3a and R 3bare independently hydrogen, optionally substituted C 1 -C 4 alkyl, and optionally substituted benzyl; Each R 4c , R 4d , R 5d , R 5e , R 6c , and R 6d are independently hydrogen, halogen, -CN, -OH, optionally substituted C 1 -C 4 Alkyl, optionally substituted C 1 -C 4 Fluoroalkyl, optionally substituted C 2 -C 6 Alkenyl, -NR 3c R 3d , -S(=O) 2 O - , -S(=O) 2 OR 9a , -C(=O)O - , and -C(=O)OR 9a is selected from Each R 3c and R 3d are independently hydrogen, optionally substituted C 1 -C 4 Alkyl, -X-optionally substituted C 1 -C 4 Alkyl, optionally substituted C 2 -C 6 alkenyl, and optionally substituted aryl; X is -C(=O)-, -S(=O)-, or -S(=O) 2 - and Each R 9a , R 11a , R 11b , R 11c , R 12a , R 12b , and R 12c are independently hydrogen, optionally substituted C 1 -C 4 alkyl, and optionally substituted aryl; n is an integer selected from 0, 1, 2, 3, 4, 5, 6, 7, and 8; s is an integer selected from 1, 2, 3, 4, or 5; t is an integer selected from 1, 2, 3, 4, or 5; p is an integer selected from 1, 2, 3, 4, or 5; x is 0.001 to 0.999, The compounds of formula (II) and formula (V) are each independently charged or zwitterionic, However, the compound of formula (II) [ka] The condition is that it is not.

[0020] In another aspect, described herein is a method for synthesizing a compound of formula (III), the method comprising reacting a compound of formula (IV), or a salt or solvate thereof, with a compound of formula (VI): [ka] During the ceremony, Each R 1a and R 1b is independently selected from hydrogen and halogen; Each R 2a and R 2b are independently selected from halogen, -CN, and optionally substituted C 1 -C 6 fluoroalkyl; Each A 1 , A 2 , and A 3 are independently -C(=O)-, -S(=O)-, -S(=O) 2 - and -S(=O)(=NR 3c )- is selected from Each B 1 , B 2 , and B. 3 are independently -O- and -NR 3c - selected from Z 1is -(CR 6c R 6d ) s - and Z 2 is -(CR 6c R 6d ) t - and E is -CN, -OR 9a , -NR 9a R 9b , -NR 9a R 9b R 9c+ , optionally substituted C 1 -C 4 Alkyl, optionally substituted C 1 -C 6 Fluoroalkyl, -S(=O) 2 O - , -S(=O) 2 OR 9a , -C(=O)O - , or -C(=O)OR 9a and Each R 4c , R 4d , R 5d , R 5e , R 6c , and R 6d are independently hydrogen, halogen, -CN, -OR 9a , optionally substituted C 1 -C 4 Alkyl, optionally substituted C 1 -C 4 Fluoroalkyl, optionally substituted C 2 -C 6 Alkenyl, -NR 3c R 3d , -S(=O) 2 O - , -S(=O) 2 OR 9a , -C(=O)O - , and -C(=O)OR 9a is selected from Each R 3c and R 3d are independently hydrogen, optionally substituted C 1 -C 4Alkyl, -X-optionally substituted C 1 -C 4 Alkyl, optionally substituted C 2 -C 6 alkenyl, and optionally substituted aryl; X is -C(=O)-, -S(=O)-, or -S(=O) 2 - and Each R 9a , R 9b , R 9c , R 11a , R 11b , R 11c , R 12a , R 12b , and R 12c are independently hydrogen, optionally substituted C 1 -C 4 alkyl, and optionally substituted aryl; n is an integer selected from 0, 1, 2, 3, 4, 5, 6, 7, and 8; s is an integer selected from 1, 2, 3, 4, or 5; t is an integer selected from 1, 2, 3, 4, or 5; x is between 0.001 and 0.999.

[0021] In one aspect, also described herein is a charged or zwitterionic copolymer modified biofouling resistant device, the device comprising: a) contacting a surface of a silicon-based device with a mixture (e.g., a solution) comprising a charged or zwitterionic copolymer; b) treating the surface of the device of step a) with a light source for a time sufficient to effect photo-grafting of a charged or zwitterionic copolymer onto the surface of the silicon-based device, thereby producing a charged or zwitterionic modified device; Charged or zwitterionic copolymers include phenylazide-based copolymers.

[0022] In another aspect, described herein is a charged or zwitterionic copolymer modified biofouling resistant device, the device comprising: a) contacting a surface of the device with a mixture (e.g., a solution) comprising a charged or zwitterionic copolymer; b) treating the surface of the device of step a) with a light source for a time sufficient to effect photo-grafting of a charged or zwitterionic copolymer onto the surface of the device, thereby producing a charged or zwitterionic modified device; The charged or zwitterionic copolymers include phenyl azide-based copolymers, the charged or zwitterionic copolymers having a number average molecular weight of about 10,000 to about 250,000.

[0023] In another aspect, described herein is a charged or zwitterionic copolymer modified biofouling resistant device, the device comprising: c) contacting the surface of the device with a mixture (e.g., a solution) comprising a charged or zwitterionic copolymer; d) treating the surface of the device of step a) with a light source for a time sufficient to effect photo-grafting of a charged or zwitterionic copolymer onto the surface of the device, thereby producing a charged or zwitterionic modified device; The charged or zwitterionic copolymers include phenyl azide-based copolymers, the charged or zwitterionic copolymers having a number average molecular weight of about 14,000 to about 21,000.

[0024] The accompanying drawings, which are incorporated in and constitute a part of this specification, illustrate several aspects and, together with the description, serve to explain but not limit the scope of the disclosure. [Brief description of the drawings]

[0025] [Figure 1] 1 illustrates a representative photografting of poly(sulfobetaine methacrylate-co-perfluorophenyl azide methacrylate) (PFPA-PSB copolymer) onto a silicone surface. [Figure 2A] Representative water advancing (top image) and receding (bottom image) contact angles for (a) an unmodified silicone surface and (b) a PFPA-PSB copolymer-modified silicone surface are illustrated. [Figure 2B] Representative water advancing contact angles (top image) and receding contact angles (bottom image) on a PFPA-PSB copolymer modified silicone surface are illustrated. [Figure 3A] Illustrates high density Escherichia coli attachment to an unmodified silicone surface forming an elastic film that ruptures upon drying of the surface. [Figure 3B] Illustrates very low density attachment of Escherichia coli to poly(sulfobetaine methacrylate-co-perfluorophenyl azide methacrylate)-modified silicone surfaces. [Figure 4] 1 illustrates the structure of a PFPA-PSB copolymer. [Figure 5A] 1 illustrates the chemical structures of polydimethylsiloxane and polysulfobetaine. [Figure 5B] FIG. 1 illustrates the XPS spectrum of PFPA-PSB modified PDMS substrate, showing the successful grafting of PSB onto the organic substrate. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0026] Additional advantages of the invention will be set forth in part in the description which follows and in part will be obvious from the description or may be learned by the practice of the invention. The advantages of the invention will be realized and attained by means of the elements and combinations particularly pointed out in the appended claims. It is to be understood that both the foregoing summary and the following detailed description are exemplary and explanatory only and are not restrictive of the invention as claimed.

[0027] Hospital-acquired infections (HAIs) are responsible for over 100,000 deaths and over $30 billion in direct health care costs annually. Despite the reduction in HAIs in recent years due to improvements in disinfection techniques, surgical procedures, and diagnostics, the decline in HAIs has slowed, indicating the need for new prevention methods. In some cases, medical devices implanted in the body are the source of infection. It is estimated that 60-70% of HAIs are associated with the use of implantable medical devices. Planktonic bacteria attach to the surface of the medical device and begin to grow into an elastic biofilm that becomes more resistant to antibiotics and disinfectants than when in a planktonic state. As the biofilm grows and the cells continue to multiply, the extracellular matrix scaffold (composed of proteins and polysaccharides) ruptures, releasing more bacteria into the body. The body is no longer able to prevent any more infections and must use powerful antibiotics to fight the infected cells. The use of powerful antibiotics has led to the existence of antibiotic-resistant bacteria, also known as superbugs, that can no longer be treated with conventional antibiotics.

[0028] Without the initial attachment of planktonic cells to the surface of the material, biofilm formation is prevented or reduced. Several researchers have identified the forces of attraction that cause organic materials to adhere to polymer surfaces: hydrophobic and electrostatic interactions (van der Waals forces) between the organic material and the polymer surface. Using self-assembled monolayers, Whitesides et al. investigated several functional groups to determine the surface functionality that promotes or hinders the nonspecific adsorption of proteins. (Whitesides, GMA survey of structure-property relationships of surfaces that resist the adsorption of protein. Langmuir, 2001, 17(18), pp5605-5620). The functional groups that showed the lowest adhesion were electrostatically neutral hydrophilic moieties that contain hydrogen bond donor groups. From these design rules, many material coatings have been developed and shown to reduce protein and microbial adhesion. However, these coatings are substrate dependent and / or require exotic reaction conditions that are not compatible with widespread use. In some cases, several polymer coatings and surface modifications have been developed to repel these interactions and reduce / prevent the formation of biofilms on surfaces. In some cases, the coating should have the following chemical requirements to be used as an anti-fouling surface: a) the coating must be hydrophilic, b) the coating should consist mainly of hydrogen bond acceptors, and c) the coating must be electrostatically neutral. However, due to the water solubility of hydrophilic coatings, the coating material must be covalently bonded to the polymer material for long-term effectiveness.

[0029] In some cases, medical grade silicones are used in the medical and healthcare industries. The market is currently experiencing rapid growth and is projected to reach $7.23 billion by 2021. Medical grade silicones generally include polydimethylsiloxane (PDMS) fluids and elastomers. Due to their good chemical stability, matching mechanical properties with human tissue, and no need for plasticizers, PDMS elastomers generally have excellent biocompatibility and are used in medical devices and biomedical implants such as catheters and pacemakers. PDMS elastomers also have high transparency and easy processability. Thus, PDMS elastomers have found widespread application in the fabrication of microfluidic devices, which provide a low-cost, simple, and robust system for diagnosing diseases (Whitesides, GM The origins and the future of microfluidics. Nature 2006, 442 (7101), 368-373). However, PDMS elastomers also have a low surface energy of about 20 mN / m. Bacteria, platelets, proteins, and other biomolecules tend to adhere to the hydrophobic surface of PDMS elastomers (Hron, P. Hydrophilisation of silicone rubber for medical applications. Polymer international 2003, 52(9), 1531-1539). In the case of silicone medical implants, bacterial adhesion and biofilm formation can lead to medical device failure, severe infection, and even patient death. In the case of disease diagnostic devices based on PDMS microfluidics, contamination of proteins and other biomolecules on the PDMS surface can significantly reduce the sensitivity of these devices and even result in complete failure of the device if blocking of the microfluidic channels occurs (Zhou, J. et al. Recent developments in PDMS surface modification for microfluidic devices. Electrophoresis 2010, 31(1), 2-16).

[0030] Hydrophilic treatment of PDMS surfaces was found to be one of the strategies to mitigate or prevent biofouling problems (Keefe, AJ et al. Suppressing surface reconstruction of superhydrophobic PDMS using a superhydrophilic zwitterionic polymer. Biomacromolecules 2012,13(5),1683-1687). Some conventional methods to make PDMS surfaces hydrophilic include oxidation of the surface by oxygen plasma, UV ozone, or corona discharge. However, these modifications are only temporary because PDMS has an extremely low glass transition temperature of about -120°C, and therefore the PDMS chains are highly mobile at room temperature. The PDMS chains are able to rearrange and restore the hydrophobic surface of the PDMS elastomer within a time frame of a few hours. In some cases, other methods seeking to create long-lasting hydrophilic PDMS surfaces require many steps and involve radical reactions or polymerization. These steps need to be carried out in a closed container and / or under the protection of inert gas. Due to the high solubility of oxygen compared to nitrogen in PDMS, in some cases it takes a long time to remove oxygen from PDMS so that the radical reactions can proceed efficiently. These stringent reaction conditions significantly increase the cost and limit the industrial applicability of these reactions.

[0031] In some embodiments, provided herein is an anti-biofouling coating comprising a charged or zwitterionic compound comprising a phenylazide moiety. In some cases, biofouling includes microbiofouling or macrobiofouling. Microbiofouling includes microbial adhesion (e.g., bacterial adhesion) and / or the formation of a biofilm. A biofilm is a group of microorganisms that adhere to a surface. In some cases, the attached microorganisms are further embedded in a self-produced matrix of extracellular polymeric material, including extracellular DNA, proteins, and polymeric agglomerates of polysaccharides. Macrobiofouling includes the attachment of larger organisms.

[0032] The charged and / or zwitterionic compounds bind to water molecules through electrostatically induced hydration. In such cases, the charged and / or zwitterionic materials exhibit surface resistance to protein / cell / bacteria attachment, biofilm formation, and / or macrobiofouling. In some embodiments, the charged or zwitterionic compounds comprise copolymers. In some embodiments, methods of making anti-biofouling coatings comprising charged or zwitterionic copolymers via polymerization reactions are also provided herein. In some embodiments, the polymerization reaction is addition polymerization, atom transfer radical polymerization (ATRP), coordination polymerization, free radical polymerization, nitroxide-mediated radical polymerization (NMP), reversible addition-fragmentation chain transfer polymerization (RAFT), or ring-opening metathesis polymerization (ROMP). In some embodiments, the ionic polymerization is anionic polymerization or cationic polymerization. In some embodiments, the polymerization reaction is reversible non-activated polymerization (RDP). In some embodiments, the polymerization reaction is free radical polymerization. In some embodiments, the polymerization reaction is atom transfer radical polymerization (ATRP). In some embodiments, the anti-biofouling coating comprising the charged or zwitterionic copolymer is grafted onto the polymeric surface of the device under UV exposure. In some other embodiments, the charged or zwitterionic copolymer is grafted onto the silicone-containing surface of the device under UV exposure. In some embodiments, the charged or zwitterionic copolymer is grafted onto the surface of the medical device under UV exposure. In some other embodiments, the charged or zwitterionic copolymer is grafted onto the silicone-containing surface of the medical device under UV exposure. In some embodiments, the charged or zwitterionic is grafted onto the polymeric surface of the medical device under UV exposure. In some other embodiments, the charged or zwitterionic copolymer is grafted onto the silicone-containing polymeric surface of the medical device under UV exposure.

[0033] In some embodiments, the charged or zwitterionic copolymer modified devices include anti-fouling properties and are used to prevent and / or reduce the incidence of biofouling. In some embodiments, the charged or zwitterionic copolymer modified medical devices include anti-fouling properties and are used to prevent and / or reduce the incidence of biofouling. In some embodiments, the charged or zwitterionic coating prevents and / or reduces the attachment of microorganisms, plants, algae, or animals to a surface.

[0034] In further embodiments, disclosed herein are compounds used to prepare the disclosed charged or zwitterionic copolymers, as well as the charged or zwitterionic copolymers themselves used within the methods disclosed herein.

[0035] I. Compound In one aspect, described herein is a compound having the structure of formula (I), or a salt or solvate thereof: [ka] During the ceremony, A is -C(=O)-, -S(=O)-, -S(=O) 2 - and -S(=O)(-NR 3 )- is selected from L is -OQ, -NR 3 Q, and -N(R 3 ) 2 Q + is selected from Q is a structure represented by the following formula: [ka] Z is -CR 6a R 6b -, -C(=O)-, -C(=NH)-, and -C(=NH)NR 7 - selected from m is an integer selected from 0, 1, 2, 3, 4, 5, 6, 7, and 8; Each R 1a and R 1bis independently selected from hydrogen and halogen; Each R 2a and R 2b are independently selected from halogen, -CN, and optionally substituted C 1 -C 6 fluoroalkyl; Each R 3 are independently hydrogen, optionally substituted C 1 -C 4 Alkyl, -X-optionally substituted C 1 -C 4 selected from alkyl, optionally substituted aryl, and -X-optionally substituted aryl; X is -C(=O)-, -S(=O)-, or -S(=O) 2 - and Each R 4a , R 4b , R 5a , R 5c , R 6a , and R 6b are independently hydrogen, halogen, -CN, -OR 9 , optionally substituted C 1 -C 4 Alkyl, optionally substituted C 1 -C 4 Fluoroalkyl, optionally substituted aryl, -NR 8a R 8b , -NR 8a R 8b R 8c+ , -S(=O) 2 O - , -S(=O) 2 OR 9 , -C(=O)O - , and -C(=O)OR 9 is selected from R 5b -OR 10b , -NR 10a R 10b , or -NR 10a R 10b R 10c+ and Each R 7 , R 8a , R8b , R 8c , and R 9 are independently hydrogen and optionally substituted C 1 -C 4 selected from alkyl and optionally substituted aryl; Each R 10a and R 10c are independently hydrogen, optionally substituted C 1 -C 4 Alkyl, optionally substituted aryl, -(optionally substituted C 1 -C 8 Alkylene)S(=O) 2 O - , -(optionally substituted C 1 -C 8 Alkylene)S(=O) 2 OH, -(optionally substituted C 1 -C 8 Alkylene)C(=O)O - , and -(optionally substituted C 1 -C 8 alkylene)C(=O)OH; R 10b is -C(=O)-C 2 -C 6 Alkenyl, -S(=O)-C 2 -C 6 Alkenyl, or -S(=O) 2 -C 2 -C 6 It is alkenyl.

[0036] In some embodiments, the compound of formula (I) is N-(2-((4-azido-2,3,5,6-tetrafluorophenyl)sulfonamido)ethyl)methacrylamide, N-(2-acrylamidoethyl)-4-azido-2,3,5,6-tetrafluorobenzamide, or Not 2-(methacryloyloxy)ethyl 4-azido-2,3,5,6-tetrafluorobenzoate.

[0037] In some embodiments, N-(2-((4-azido-2,3,5,6-tetrafluorophenyl)sulfonamido)ethyl)methacrylamide is [ka] In some embodiments, N-(2-acrylamidoethyl)-4-azido-2,3,5,6-tetrafluorobenzamide has the structure: [ka] In some embodiments, N-(2-acrylamidoethyl)-4-azido-2,3,5,6-tetrafluorobenzamide has the structure: [ka] It has the structure:

[0038] In some embodiments, the compound of formula (I) is [ka] The structure is selected from:

[0039] In some embodiments, the compound of formula (I) is [ka] The structure is selected from:

[0040] In some embodiments, the compound of formula (I) has the following structure: [ka] has.

[0041] In some embodiments, the compound of formula (I) is [ka] The structure is selected from:

[0042] In some embodiments, the compound of formula (I) is [ka] The structure is selected from:

[0043] In some embodiments, each R 1a and R 1b is independently halogen. In some embodiments, each R 1a and R 1b is independently F or Cl. In some embodiments, each R 1a and R 1b is F. In some embodiments, each R 2a and R 2b are independently selected from halogen, -CN, and optionally substituted C 1 -C 6 In some embodiments, each R 2a and R 2b are independently halogen, -CN, and -CF 3 In some embodiments, each R 2a and R 2b are independently F, Cl, -CN, and -CF 3 In some embodiments, each R 2a and R 2b is independently halogen. In some embodiments, each R 2a and R 2b is F. In some embodiments, each R 2a and R 2b In some embodiments, each R 2a and R 2b is independently 1 -C 6 In some embodiments, each R 2a and R 2b -CF 3 It is.

[0044] In some embodiments, each R 1a , R 1b , R 2a , and R 2b is F.

[0045] In some embodiments, Z is -CR 6a R 6b -, -C(=O)-, -C(=NH)-, and -C(=NH)NR 7 In some embodiments, Z is selected from -CR 6a R 6b In some embodiments, Z is -C(=O)-. In some embodiments, Z is -C(=NH)-. In some embodiments, Z is -C(=NH)NR 7 -It is.

[0046] In some embodiments, each R 3 are independently hydrogen, optionally substituted C 1 -C 4 Alkyl, -X-optionally substituted C 1 -C 4 In some embodiments, R is selected from alkyl, optionally substituted aryl, and -X-optionally substituted aryl. 3 is hydrogen. In some embodiments, R 3 is an optionally substituted C 1 -C 4 In some embodiments, R 3 is -X-optionally substituted C 1 -C 4 In some embodiments, R 3 is optionally substituted aryl. In some embodiments, R 3 is -X-optionally substituted aryl.

[0047] In some embodiments, X is -C(=O)-, -S(=O)-, or -S(=O) 2In some embodiments, X is -C(=O)-. In some embodiments, X is -S(=O)-. In some embodiments, X is -S(=O) 2 -It is.

[0048] In some embodiments, each R 6a and R 6b is hydrogen.

[0049] In some embodiments, m is 0, 1, 2, 3, 4, 5, or 6. In some embodiments, m is 0, 1, 2, 3, 4, or 5. In some embodiments, m is 0, 1, 2, or 3. In some embodiments, m is 0. In some embodiments, m is 1. In some embodiments, m is 2. In some embodiments, m is 3. In some embodiments, m is 4. In some embodiments, m is 5.

[0050] In some embodiments, R 5a is hydrogen and R 5b -NR 10a R 10b and R 5c is hydrogen.

[0051] In some embodiments, R 5a is hydrogen and R 5b -OR 10b and R 5c is hydrogen.

[0052] In some embodiments, R 4a is hydrogen and R 4b is hydrogen.

[0053] In some embodiments, the compound of formula (I) has the formula (Ia): [ka] It has the structure:

[0054] In some embodiments, the compound of formula (I) has formula (Ib): [ka] It has the structure:

[0055] In some embodiments, the compound of formula (I) has the formula (Ic): [ka] It has the structure:

[0056] In some embodiments, the compound of formula (I) has the formula (Id): [ka] It has the structure:

[0057] In some embodiments, R 10a is hydrogen, optionally substituted C 1 -C 4 In some embodiments, R 10a is hydrogen. In some embodiments, R 10a is an optionally substituted C 1 -C 4 In some embodiments, R 10a is CH 3 In some embodiments, R 10a is CH 2 CH 3 In some embodiments, R 10a is optionally substituted aryl. In some embodiments, R 10a is phenyl.

[0058] In some embodiments, the compound of formula (I) has the formula (Ie): [ka] It has the structure:

[0059] In some embodiments, the compound of formula (I) has the formula (If): [ka] It has the structure:

[0060] In some embodiments, the compound of formula (I) has the formula (Ig): [ka] It has the structure:

[0061] In some embodiments, the compound of formula (I) has the formula (Ih): [ka] It has the structure:

[0062] In some embodiments, R 10b is -C(=O)-C 2 -C 6 Alkenyl, -S(=O)-C 2 -C 6 Alkenyl, or -S(=O) 2 -C 2 -C 6 In some embodiments, R is alkenyl. 10b is -C(=O)-C 2 -C 6 In some embodiments, R is alkenyl. 10b is -(S=O)-C 2 -C 6 In some embodiments, R is alkenyl. 10b is -S(=O) 2 -C 2 -C 6 It is alkenyl.

[0063] In some embodiments, the compound of formula (I) is [ka] is selected from.

[0064] In some embodiments, the compound of formula (I) is [ka] is selected from.

[0065] In some embodiments, the compound of formula (I) is [ka] is selected from.

[0066] In some embodiments, the compound of formula (I) is [ka] is selected from.

[0067] In some embodiments, the compound of formula (I) is [ka] is selected from.

[0068] In some embodiments, the compound of formula (I) is [ka] is selected from.

[0069] In some embodiments, the compound of formula (I) is [ka] is selected from.

[0070] In some embodiments, the compound of formula (I) is [ka] is selected from.

[0071] In another aspect, there is provided a compound described herein having the structure of formula (II), or a salt or solvate thereof: [ka] During the ceremony, Each R 1a and R 1b is independently selected from hydrogen and halogen; Each R 2a and R 2b are independently selected from halogen, -CN, and optionally substituted C 1 -C 6 fluoroalkyl; Each A 1 , A 2 , and A 3 are independently -C(=O)-, -S(=O)-, -S(=O) 2 - and -S(=O)(=NR 3c )- is selected from Each B 1 , B 2 , and B. 3 are independently -O- and -NR 3c - selected from D is -S(=O) 2 O - , -S(=O) 2 OR 9a , -C(=O)O - , or -C(=O)OR 9a and Z 1 is -(CR 6c R 6d ) s - and Z 2 is -(CR 6c R 6d ) t - and Z 3 is -(CR 6c R 6d ) p - and Each R 3a and R 3b are independently hydrogen, optionally substituted C 1 -C4 alkyl, and optionally substituted benzyl; Each R 4c , R 4d , R 5d , R 5e , R 6c , and R 6d are independently hydrogen, halogen, -CN, -OR 9a , optionally substituted C 1 -C 4 Alkyl, optionally substituted C 1 -C 4 Fluoroalkyl, optionally substituted C 2 -C 6 Alkenyl, -NR 3c R 3d , -S(=O) 2 O - , -S(=O) 2 OR 9a , -C(=O)O - , and -C(=O)OR 9a is selected from Each R 3c and R 3d are independently hydrogen, optionally substituted C 1 -C 4 Alkyl, -X-optionally substituted C 1 -C 4 Alkyl, optionally substituted C 2 -C 6 alkenyl, and optionally substituted aryl; X is -C(=O)-, -S(=O)-, or -S(=O) 2 - and Each R 9a , R 11a , R 11b , R 11c , R 12a , R 12b , and R 12c are independently hydrogen, optionally substituted C 1 -C 4 alkyl, and optionally substituted aryl; n is an integer selected from 0, 1, 2, 3, 4, 5, 6, 7, and 8; s is an integer selected from 1, 2, 3, 4, or 5; t is an integer selected from 1, 2, 3, 4, or 5; p is an integer selected from 1, 2, 3, 4, or 5; 0 <x<1であり、 The compounds of formula (II) are charged or zwitterionic.

[0072] In some embodiments, the compound of formula (II) is [ka] isn't it.

[0073] In some embodiments, x in formula (II) is not about 0.9434.

[0074] In some embodiments, the compound of formula (II) is not obtained by using 2 g of sulfobetaine methacrylate monomer and 156 mg of perfluorophenyl azide methacrylamide monomer.

[0075] In some embodiments, each R 1a and R 1b is independently halogen. In some embodiments, each R 1a and R 1b is independently F or Cl. In some embodiments, each R 1a and R 1b is F. In some embodiments, each R 2a and R 2b are independently selected from halogen, -CN, and optionally substituted C 1 -C 6 In some embodiments, each R 2a and R 2b are independently halogen, -CN, and -CF 3 In some embodiments, each R2a and R 2b are independently F, Cl, -CN, and -CF 3 In some embodiments, each R 2a and R 2b is independently halogen. In some embodiments, each R 2a and R 2b is F. In some embodiments, each R 2a and R 2b In some embodiments, each R 2a and R 2b is independently 1 -C 6 In some embodiments, each R 2a and R 2b -CF 3 It is.

[0076] In some embodiments, each R 1a , R 1b , R 2a , and R 2b is F.

[0077] In some embodiments, A 1 is -S(=O) 2 In some embodiments, A 1 is -C(=O)-.

[0078] In some embodiments, A 2 is -S(=O) 2 In some embodiments, A 2 is -C(=O)-.

[0079] In some embodiments, A 3 is -S(=O) 2 In some embodiments, A 3 is -C(=O)-.

[0080] In some embodiments, each B 1 and B. 2 -NR3c -It is.

[0081] In some embodiments, each R 3c are independently hydrogen, optionally substituted C 1 -C 4 In some embodiments, R 3c is hydrogen. In some embodiments, R 3c is an optionally substituted C 1 -C 4 In some embodiments, R 3c -CH 3 In some embodiments, R 3c is optionally substituted aryl. In some embodiments, R 3c is optionally substituted phenyl.

[0082] In some embodiments, B 3 is -O-.

[0083] In some embodiments, D is -S(=O) 2 OR 9a OR -C(=O)OR 9a In some embodiments, D is -S(=O) 2 OR 9a In some embodiments, D is -C(=O)OR 9a It is.

[0084] In some embodiments, R 9a is hydrogen or -CH 3 In some embodiments, R 9a is hydrogen. In some embodiments, R 9a -CH 3 It is.

[0085] In some embodiments, D is -S(=O) 2 O - or -C(=O)O -In some embodiments, D is -S(=O) 2 O - In some embodiments, D is -C(=O)O - It is.

[0086] In some embodiments, each R 6c and R 6d is hydrogen.

[0087] In some embodiments, each R 3a and R 3b are independently hydrogen or C 1 -C 4 In some embodiments, each R 3a and R 3b are independently hydrogen or -CH 3 In some embodiments, each R 3a and R 3b is hydrogen. In some embodiments, each R 3a and R 3b -CH 3 It is.

[0088] In some embodiments, each R 4c and R 4d are independently hydrogen or -CH 3 In some embodiments, each R 4c and R 4d is hydrogen. In some embodiments, each R 4c and R 4d -CH 3 In some embodiments, R 4c is hydrogen and R 4d -CH 3 It is.

[0089] In some embodiments, each R 5d and R 5e are independently hydrogen or -CH 3 In some embodiments, each R 5d and R 5e is hydrogen. In some embodiments, each R5d and R 5e -CH 3 In some embodiments, R 5d is hydrogen and R 5e -CH 3 It is.

[0090] In some embodiments, R 11a is hydrogen or -CH 3 In some embodiments, R 11a is hydrogen. In some embodiments, R 11a -CH 3 It is.

[0091] In some embodiments, R 12a is hydrogen or -CH 3 In some embodiments, R 12a is hydrogen. In some embodiments, R 12a -CH 3 It is.

[0092] In some embodiments, each R 11b , R 11c , R 12b , and R 12c is hydrogen.

[0093] In some embodiments, n is 0, 1, 2, 3, 4, 5, or 6. In some embodiments, n is 0, 1, 2, 3, 4, or 5. In some embodiments, n is 0. In some embodiments, n is 1. In some embodiments, n is 2. In some embodiments, n is 3. In some embodiments, n is 4. In some embodiments, n is 5.

[0094] In some embodiments, s is 1, 2, 3, or 4. In some embodiments, s is 1. In some embodiments, s is 2. In some embodiments, s is 3. In some embodiments, s is 4.

[0095] In some embodiments, t is 1, 2, 3, or 4. In some embodiments, t is 1. In some embodiments, t is 2. In some embodiments, t is 3. In some embodiments, t is 4.

[0096] In some embodiments, p is 1, 2, 3, or 4. In some embodiments, p is 1. In some embodiments, p is 2. In some embodiments, p is 3. In some embodiments, p is 4.

[0097] In some embodiments, x is greater than 0. In some embodiments, x is less than 1. In some embodiments, x is 0.0000001 to 0.9999999. In some embodiments, x is 0.00001 to 0.99999. In some embodiments, x is 0.001 to 0.999. In some embodiments, x is 0.01 to 0.99. In some embodiments, x is 0.1 to 0.99. In some embodiments, x is 0.2 to 0.99. In some embodiments, x is 0.3 to 0.99. In some embodiments, x is 0.5 to 0.99. In some embodiments, x is 0.5 to 0.99. In some embodiments, x is 0.6 to 0.99. In some embodiments, x is 0.7 to 0.99. In some embodiments, x is 0.8 to 0.99. In some embodiments, x is between 0.9 and 0.99. In some embodiments, x is between 0.91 and 0.99. In some embodiments, x is between 0.92 and 0.99.

[0098] In some embodiments, x is at least 0.0000001, at least 0.00001, at least 0.001, at least 0.01, at least 0.02, at least 0.03, at least 0.04, at least 0.05, at least 0.07, at least 0.09, at least 0.11, at least 0.15, at least 0.20, at least 0.23, at least 0.28, at least 0.35, at least 0.42, at least 0.5, at least 0.53, at least 0.58, at least 0.63, at least 0.67, at least 0.82, at least 0.86, at least 0.88, at least 0.89, at least 0.92, at least 0.96, at least 0.98, at least 0.99, at least 10 ... at least 0.71, at least 0.75, at least 0.78, at least 0.79, at least 0.80, at least 0.81, at least 0.82, at least 0.83, at least 0.84, at least 0.85, at least 0.86, at least 0.87, at least 0.88, at least 0.89, at least 0.9, at least 0.91, at least 0.92, at least 0.93, at least 0.94, at least 0.95, at least 0.96, at least 0.97, at least 0.98, or at least 0.99.

[0099] In some embodiments, x is up to 0.9999999, up to 0.99999, up to 0.999, up to 0.99, up to 0.98, up to 0.97, up to 0.96, up to 0.95, up to 0.94, up to 0.93, up to 0.92, up to 0.91, up to 0.90, up to 0.89, up to 0.88, up to 0.87, up to 0.86, up to 0.85, up to 0.84, up to 0.83, up to 0.82, up to 0.81, up to 0.8 0, max 0.79, max 0.78, max 0.77, max 0.76, max 0.75, max 0.74, max 0.70, max 0.66, max 0.62, max 0.59, max 0.56, max 0.53, max 0.50, max 0.47, max 0.43, max 0.39, max 0.34, max 0.29, max 0.25, max 0.21, max 0.18, max 0.14, max 0.10, max 0.07, or max 0.04.

[0100] In some embodiments, x is from about 0.89 to about 0.999. In some embodiments, x is at least about 0.89. In some embodiments, x is up to about 0.999. In some embodiments, x is from about 0.89 to about 0.9, from about 0.89 to about 0.91, from about 0.89 to about 0.92, from about 0.89 to about 0.93, from about 0.89 to about 0.94, from about 0.89 to about 0.95, from about 0.89 to about 0.96, from about 0.89 to about 0.97, from about 0.89 to about 0.98, from about 0.89 to about 0.99, from about 0.89 to about 0.999, from about 0.9 to about 0.91, from about 0.9 to about 0.92, from about 0.9 to about 0.93, from about 0.9 to about 0.94, from about 0.9 to about 0.95, from about 0.9 to about 0.96, about 0.9 to about 0.97, about 0.9 to about 0.98, about 0.9 to about 0.99, about 0.9 to about 0.999, about 0.91 to about 0.92, about 0.91 to about 0.93, about 0.91 to about 0.94, about 0.91 to about 0.95, about 0.91 to about 0.96, about 0.91 to about 0.97, about 0.91 to about 0.98, about 0.91 to about 0.99, about 0.91 to about 0.999, about 0.92 to about 0.93, about 0.92 to about 0.94, about 0.92 to about 0.95, about 0. 0.92 to about 0.96, about 0.92 to about 0.97, about 0.92 to about 0.98, about 0.92 to about 0.99, about 0.92 to about 0.999, about 0.93 to about 0.94, about 0.93 to about 0.95, about 0.93 to about 0.96, about 0.93 to about 0.97, about 0.93 to about 0.98, about 0.93 to about 0.99, about 0.93 to about 0.999, about 0.94 to about 0.95, about 0.94 to about 0.96, about 0.94 to about 0.97, about 0.94 to about 0.98, about 0.94 to about 0.99, about 0.94 to about 0.999, about 0.95 to about 0.96, about 0.95 to about 0.97, about 0.95 to about 0.98, about 0.95 to about 0.99, about 0.95 to about 0.999, about 0.96 to about 0.97, about 0.96 to about 0.98, about 0.96 to about 0.99, about 0.96 to about 0.999, about 0.97 to about 0.98, about 0.97 to about 0.99, about 0.97 to about 0.999, about 0.98 to about 0.99, about 0.98 to about 0.999, or about 0.99 to about 0.999. In some embodiments, x is about 0.89, about 0.9, about 0.91, about 0.92, about 0.93, about 0.94, about 0.95, about 0.96, about 0.97, about 0.98, about 0.99, or about 0.999.

[0101] In another aspect, described herein is a compound having the structure of formula (III), or a salt or solvate thereof: [ka] During the ceremony, Each R 1a and R 1b is independently selected from hydrogen and halogen; Each R 2a and R 2b are independently selected from halogen, -CN, and optionally substituted C 1 -C 6 fluoroalkyl; Each A 1 , A 2 , and A 3 are independently -C(=O)-, -S(=O)-, -S(=O) 2 - and -S(=O)(=NR 3c )- is selected from Each B 1 , B 2 , and B. 3 are independently -O- and -NR 3c - selected from Z 1 is -(CR 6c R 6d ) s - and Z 2 is -(CR 6c R 6d ) t - and E is -CN, -OR 9a , -NR 9a R 9b , -NR 9a R 9b R 9c+ , optionally substituted C 1 -C 4 Alkyl, optionally substituted C 1 -C 6 Fluoroalkyl, -S(=O) 2 O - , -S(=O) 2OR 9a , -C(=O)O - , or -C(=O)OR 9a and Each R 4c , R 4d , R 5d , R 5e , R 6c , and R 6d are independently hydrogen, halogen, -CN, -OR 9a , optionally substituted C 1 -C 4 Alkyl, optionally substituted C 1 -C 4 Fluoroalkyl, optionally substituted C 2 -C 6 Alkenyl, -NR 3c R 3d , -S(=O) 2 O - , -S(=O) 2 OR 9a , -C(=O)O - , and -C(=O)OR 9a is selected from Each R 3c and R 3d are independently hydrogen, optionally substituted C 1 -C 4 Alkyl, -X-optionally substituted C 1 -C 4 Alkyl, optionally substituted C 2 -C 6 alkenyl, and optionally substituted aryl; X is -C(=O)-, -S(=O)-, or -S(=O) 2 - and Each R 9a , R 9b , R 9c , R 11a , R 11b , R 11c , R 12a , R 12b , and R 12c are independently hydrogen, optionally substituted C 1 -C 4alkyl, and optionally substituted aryl; n is an integer selected from 0, 1, 2, 3, 4, 5, 6, 7, and 8; s is an integer selected from 1, 2, 3, 4, or 5; t is an integer selected from 1, 2, 3, 4, or 5; 0 <x<1である。

[0102] In some embodiments, the compound of formula (III) is charged or zwitterionic. In some embodiments, the compound of formula (III) comprises a positively charged repeat unit. In some embodiments, the compound of formula (III) comprises a negatively charged repeat unit. In some embodiments, the compound of formula (III) comprises a positively charged repeat unit and a negatively charged repeat unit. In some embodiments, the ratio of the positively charged repeat unit to the negatively charged repeat unit in the compound of formula (III) is about 10:1 to about 1:10. In some embodiments, the ratio of the positively charged repeat unit to the negatively charged repeat unit in the compound of formula (III) is about 5:1 to about 1:5. In some embodiments, the ratio of the positively charged repeat unit to the negatively charged repeat unit in the compound of formula (III) is about 2:1 to about 1:2. In some embodiments, the ratio of the positively charged repeat unit to the negatively charged repeat unit in the compound of formula (III) is about 1:1.

[0103] In some embodiments, each R 1a and R 1b is independently halogen. In some embodiments, each R 1a and R 1b is independently F or Cl. In some embodiments, each R 1a and R 1b is F. In some embodiments, each R 2a and R 2b are independently selected from halogen, -CN, and optionally substituted C 1 -C 6 In some embodiments, each R 2a and R2b are independently halogen, -CN, and -CF 3 In some embodiments, each R 2a and R 2b are independently F, Cl, -CN, and -CF 3 In some embodiments, each R 2a and R 2b is independently halogen. In some embodiments, each R 2a and R 2b is F. In some embodiments, each R 2a and R 2b In some embodiments, each R 2a and R 2b is independently 1 -C 6 In some embodiments, each R 2a and R 2b -CF 3 It is.

[0104] In some embodiments, each R 1a , R 1b , R 2a , and R 2b is F.

[0105] In some embodiments, A 1 is -S(=O) 2 In some embodiments, A 1 is -C(=O)-.

[0106] In some embodiments, A 2 is -S(=O) 2 In some embodiments, A 2 is -C(=O)-.

[0107] In some embodiments, A 3 is -S(=O) 2 In some embodiments, A 3 is -C(=O)-.

[0108] In some embodiments, each B 1 , B 2 , and B. 3 -NR 3c -It is.

[0109] In some embodiments, each R 3c are independently hydrogen, optionally substituted C 1 -C 4 In some embodiments, R 3c is hydrogen. In some embodiments, R 3c is an optionally substituted C 1 -C 4 In some embodiments, R 3c -CH 3 In some embodiments, R 3c is optionally substituted aryl. In some embodiments, R 3c is optionally substituted phenyl.

[0110] In some embodiments, E is -NR 9a R 9b R 9c+ or -S(=O) 2 OR 9a It is.

[0111] In some embodiments, E is -NR 9a R 9b R 9c+ In some embodiments, each R 9a , R 9b , and R 9c are independently hydrogen or C 1 -C 4 In some embodiments, each R 9a , R 9b , and R 9c are independently hydrogen or -CH 3 In some embodiments, R 9a is hydrogen. In some embodiments, R 9a -CH3 In some embodiments, R 9b is hydrogen. In some embodiments, R 9b -CH 3 In some embodiments, R 9c is hydrogen. In some embodiments, R 9c -CH 3 It is.

[0112] In some embodiments, E is -S(=O) 2 OR 9a In some embodiments, each R 9a is hydrogen or -CH 3 In some embodiments, R 9a is hydrogen. In some embodiments, R 9a -CH 3 It is.

[0113] In some embodiments, E is -S(=O) 2 O - or -C(=O)O - In some embodiments, E is -S(=O) 2 O - In some embodiments, E is -C(=O)O - It is.

[0114] In some embodiments, each R 6c and R 6d are independently hydrogen and -CH 3 In some embodiments, each R 6c and R 6d is hydrogen. In some embodiments, each R 6c and R 6d -CH 3 It is.

[0115] In some embodiments, each R 4c and R 4d are independently hydrogen or -CH 3 In some embodiments, each R 4c and R4d is hydrogen. In some embodiments, each R 4c and R 4d -CH 3 In some embodiments, R 4c is hydrogen and R 4d -CH 3 It is.

[0116] In some embodiments, each R 5d and R 5e are independently hydrogen or -CH 3 In some embodiments, each R 5d and R 5e is hydrogen. In some embodiments, each R 5d and R 5e -CH 3 In some embodiments, R 5d is hydrogen and R 5e -CH 3 It is.

[0117] In some embodiments, R 11a is hydrogen or -CH 3 In some embodiments, R 11a is hydrogen. In some embodiments, R 11a -CH 3 It is.

[0118] In some embodiments, R 12a is hydrogen or -CH 3 In some embodiments, R 12a is hydrogen. In some embodiments, R 12a -CH 3 It is.

[0119] In some embodiments, each R 11b , R 11c , R 12b , and R 12c is hydrogen.

[0120] In some embodiments, n is 0, 1, 2, 3, 4, 5, or 6. In some embodiments, n is 0, 1, 2, 3, 4, or 5. In some embodiments, n is 0. In some embodiments, n is 1. In some embodiments, n is 2. In some embodiments, n is 3. In some embodiments, n is 4. In some embodiments, n is 5.

[0121] In some embodiments, s is 1, 2, 3, or 4. In some embodiments, s is 1. In some embodiments, s is 2. In some embodiments, s is 3. In some embodiments, s is 4.

[0122] In some embodiments, t is 1, 2, 3, or 4. In some embodiments, t is 1. In some embodiments, t is 2. In some embodiments, t is 3. In some embodiments, t is 4.

[0123] In some embodiments, x is greater than 0. In some embodiments, x is less than 1. In some embodiments, x is 0.0000001 to 0.9999999. In some embodiments, x is 0.00001 to 0.99999. In some embodiments, x is 0.001 to 0.999. In some embodiments, x is 0.01 to 0.99. In some embodiments, x is 0.1 to 0.99. In some embodiments, x is 0.2 to 0.99. In some embodiments, x is 0.3 to 0.99. In some embodiments, x is 0.5 to 0.99. In some embodiments, x is 0.5 to 0.99. In some embodiments, x is 0.6 to 0.99. In some embodiments, x is 0.7 to 0.99. In some embodiments, x is 0.8 to 0.99. In some embodiments, x is between 0.9 and 0.99. In some embodiments, x is between 0.91 and 0.99. In some embodiments, x is between 0.92 and 0.99.

[0124] In some embodiments, x is at least 0.0000001, at least 0.00001, at least 0.001, at least 0.01, at least 0.02, at least 0.03, at least 0.04, at least 0.05, at least 0.07, at least 0.09, at least 0.11, at least 0.15, at least 0.20, at least 0.23, at least 0.28, at least 0.35, at least 0.42, at least 0.5, at least 0.53, at least 0.58, at least 0.63, at least 0.67, at least 0.82, at least 0.86, at least 0.88, at least 0.89, at least 0.92, at least 0.96, at least 0.98, at least 0.99, at least 10 ... at least 0.71, at least 0.75, at least 0.78, at least 0.79, at least 0.80, at least 0.81, at least 0.82, at least 0.83, at least 0.84, at least 0.85, at least 0.86, at least 0.87, at least 0.88, at least 0.89, at least 0.9, at least 0.91, at least 0.92, at least 0.93, at least 0.94, at least 0.95, at least 0.96, at least 0.97, at least 0.98, or at least 0.99.

[0125] In some embodiments, x is up to 0.9999999, up to 0.99999, up to 0.999, up to 0.99, up to 0.98, up to 0.97, up to 0.96, up to 0.95, up to 0.94, up to 0.93, up to 0.92, up to 0.91, up to 0.90, up to 0.89, up to 0.88, up to 0.87, up to 0.86, up to 0.85, up to 0.84, up to 0.83, up to 0.82, up to 0.81, up to 0.8 0, max 0.79, max 0.78, max 0.77, max 0.76, max 0.75, max 0.74, max 0.70, max 0.66, max 0.62, max 0.59, max 0.56, max 0.53, max 0.50, max 0.47, max 0.43, max 0.39, max 0.34, max 0.29, max 0.25, max 0.21, max 0.18, max 0.14, max 0.10, max 0.07, or max 0.04.

[0126] In some embodiments, x is from about 0.89 to about 0.999. In some embodiments, x is at least about 0.89. In some embodiments, x is up to about 0.999. In some embodiments, x is from about 0.89 to about 0.9, from about 0.89 to about 0.91, from about 0.89 to about 0.92, from about 0.89 to about 0.93, from about 0.89 to about 0.94, from about 0.89 to about 0.95, from about 0.89 to about 0.96, from about 0.89 to about 0.97, from about 0.89 to about 0.98, from about 0.89 to about 0.99, from about 0.89 to about 0.999, from about 0.9 to about 0.91, from about 0.9 to about 0.92, from about 0.9 to about 0.93, from about 0.9 to about 0.94, from about 0.9 to about 0.95, from about 0.9 to about 0.96, about 0.9 to about 0.97, about 0.9 to about 0.98, about 0.9 to about 0.99, about 0.9 to about 0.999, about 0.91 to about 0.92, about 0.91 to about 0.93, about 0.91 to about 0.94, about 0.91 to about 0.95, about 0.91 to about 0.96, about 0.91 to about 0.97, about 0.91 to about 0.98, about 0.91 to about 0.99, about 0.91 to about 0.999, about 0.92 to about 0.93, about 0.92 to about 0.94, about 0.92 to about 0.95, about 0. 0.92 to about 0.96, about 0.92 to about 0.97, about 0.92 to about 0.98, about 0.92 to about 0.99, about 0.92 to about 0.999, about 0.93 to about 0.94, about 0.93 to about 0.95, about 0.93 to about 0.96, about 0.93 to about 0.97, about 0.93 to about 0.98, about 0.93 to about 0.99, about 0.93 to about 0.999, about 0.94 to about 0.95, about 0.94 to about 0.96, about 0.94 to about 0.97, about 0.94 to about 0.98, about 0.94 to about 0.99, about 0.94 to about 0.999, about 0.95 to about 0.96, about 0.95 to about 0.97, about 0.95 to about 0.98, about 0.95 to about 0.99, about 0.95 to about 0.999, about 0.96 to about 0.97, about 0.96 to about 0.98, about 0.96 to about 0.99, about 0.96 to about 0.999, about 0.97 to about 0.98, about 0.97 to about 0.99, about 0.97 to about 0.999, about 0.98 to about 0.99, about 0.98 to about 0.999, or about 0.99 to about 0.999. In some embodiments, x is about 0.89, about 0.9, about 0.91, about 0.92, about 0.93, about 0.94, about 0.95, about 0.96, about 0.97, about 0.98, about 0.99, or about 0.999.

[0127] In another aspect, a copolymer is described herein, the copolymer comprising: a) a repeating unit of formula (VII): [ka] (In the formula, Each R 1a and R 1b is independently selected from hydrogen and halogen; Each R 2a and R 2b are independently selected from halogen, -CN, and optionally substituted C 1 -C 6 fluoroalkyl; Each A 1 and A 2 are independently -C(=O)-, -S(=O)-, -S(=O) 2 - and -S(=O)(=NR 3c )- is selected from Each B 1 and B. 2 are independently -O- and -NR 3c - selected from Z 1 is -(CR 6c R 6d ) s - and Each R 4c , R 4d , R 5d , R 5e , R 6c , and R 6d are independently hydrogen, halogen, -CN, -OR 9a , optionally substituted C 1 -C 4 Alkyl, optionally substituted C 1 -C 4 Fluoroalkyl, optionally substituted C 2 -C 6 Alkenyl, -NR 3c R 3d , -S(=O) 2 O - , -S(=O)2 OR 9a , -C(=O)O - , and -C(=O)OR 9a is selected from Each R 3c and R 3d are independently hydrogen, optionally substituted C 1 -C 4 Alkyl, -X-optionally substituted C 1 -C 4 Alkyl, optionally substituted C 2 -C 6 alkenyl, and optionally substituted aryl; X is -C(=O)-, -S(=O)-, or -S(=O) 2 - and Each R 9a , R 11a , R 11b , and R 11c are independently hydrogen, optionally substituted C 1 -C 4 alkyl, and optionally substituted aryl; n is an integer selected from 0, 1, 2, 3, 4, 5, 6, 7, and 8; s is an integer selected from 1, 2, 3, 4, and 5; b) A repeating unit of formula (VIII): [ka] (In the formula, A 3 -C(=O)-, -S(=O)-, -S(=O) 2 - or -S(=O)(=NR 3c )-and B 3 is -O- or -NR 3c - and D is -S(=O) 2 O - , -S(=O) 2 OR 9a , -C(=O)O - , or -C(=O)OR 9a and Z 2 is -(CR 6c R 6d ) t - and Z 3 is -(CR 6c R 6d ) p - and Each R 3a and R 3b are independently hydrogen, optionally substituted C 1 -C 4 alkyl, and optionally substituted benzyl; Each R 6c and R 6d are independently hydrogen, halogen, -CN, -OR 9a , optionally substituted C 1 -C 4 Alkyl, optionally substituted C 1 -C 4 Fluoroalkyl, optionally substituted C 2 -C 6 Alkenyl, -NR 3c R 3d , -S(=O) 2 O - , -S(=O) 2 OR 9a , -C(=O)O - , and -C(=O)OR 9a is selected from Each R 3c and R 3d are independently hydrogen, optionally substituted C 1 -C 4 Alkyl, -X-optionally substituted C 1 -C 4 Alkyl, optionally substituted C 2 -C 6 alkenyl, and optionally substituted aryl; X is -C(=O)-, -S(=O)-, or -S(=O) 2 - and Each R 9a , R 12a , R 12b , and R12c are independently hydrogen, optionally substituted C 1 -C 4 alkyl, and optionally substituted aryl; t is an integer selected from 1, 2, 3, 4, or 5; p is an integer selected from 1, 2, 3, 4, or 5; A repeat unit of formula (VIII), wherein the repeat unit of formula (VIII) is charged or zwitterionic; c) A repeating unit of formula (IX): [ka] (A 4 -C(=O)-, -S(=O)-, -S(=O) 2 - or -S(=O)(=NR 3c )-and B 4 is -O- or -NR 3c - and Z 4 is -(CR 6c R 6d ) k - and E is -CN, -OR 9a , -NR 9a R 9b , -NR 9a R 9b R 9c+ , optionally substituted C 1 -C 4 Alkyl, optionally substituted C 1 -C 6 Fluoroalkyl, -S(=O) 2 O - , -S(=O) 2 OR 9a , -C(=O)O - , or -C(=O)OR 9a and Each R 6c and R 6d are independently hydrogen, halogen, -CN, -OR 9a , optionally substituted C 1 -C 4Alkyl, optionally substituted C 1 -C 4 Fluoroalkyl, optionally substituted C 2 -C 6 Alkenyl, -NR 3c R 3d , -S(=O) 2 O - , -S(=O) 2 OR 9a , -C(=O)O - , and -C(=O)OR 9a is selected from Each R 3c and R 3d are independently hydrogen, optionally substituted C 1 -C 4 Alkyl, -X-optionally substituted C 1 -C 4 Alkyl, optionally substituted C 2 -C 6 alkenyl, and optionally substituted aryl; X is -C(=O)-, -S(=O)-, or -S(=O) 2 - and Each R 9a , R 9b , R 9c , R 13a , R 13b , and R 13c are independently hydrogen, optionally substituted C 1 -C 4 alkyl, and optionally substituted aryl; and k is an integer selected from 1 to 10.

[0128] In some embodiments, the recurring unit of formula (IX) is charged or zwitterionic.

[0129] In some embodiments, each R 1a and R 1b is independently halogen. In some embodiments, each R 1a and R 1bis independently F or Cl. In some embodiments, each R 1a and R 1b is F. In some embodiments, each R 2a and R 2b are independently selected from halogen, -CN, and optionally substituted C 1 -C 6 In some embodiments, each R 2a and R 2b are independently halogen, -CN, and -CF 3 In some embodiments, each R 2a and R 2b are independently F, Cl, -CN, and -CF 3 In some embodiments, each R 2a and R 2b is independently halogen. In some embodiments, each R 2a and R 2b is F. In some embodiments, each R 2a and R 2b In some embodiments, each R 2a and R 2b is independently 1 -C 6 In some embodiments, each R 2a and R 2b -CF 3 In some embodiments, each R 1a , R 1b , R 2a , and R 2b is F.

[0130] In some embodiments, A 1 is -S(=O) 2 In some embodiments, A 1 In some embodiments, A is -C(=O)-. 2 is -S(=O) 2 In some embodiments, A 2 In some embodiments, A is -C(=O)-.3 is -S(=O) 2 In some embodiments, A 3 In some embodiments, A is -C(=O)-. 4 is -S(=O) 2 In some embodiments, A 4 In some embodiments, A is -C(=O)-. 1 is -S(=O) 2 - and each A 2 , A 3 , and A 4 is -C(=O)-. In some embodiments, each A 1 , A 2 , A 3 , and A 4 is -C(=O)-.

[0131] In some embodiments, each B 1 , B 2 , and B. 3 are independently -O- or -NR 3c In some embodiments, B 1 In some embodiments, B 1 -NR 3c In some embodiments, B 2 In some embodiments, B 2 -NR 3c In some embodiments, B 3 In some embodiments, B 3 -NR 3c In some embodiments, B 4 In some embodiments, B 4 -NR 3c -It is.

[0132] In some embodiments, each R 3c are independently hydrogen, optionally substituted C 1 -C 4 In some embodiments, R3c is hydrogen. In some embodiments, R 3c is an optionally substituted C 1 -C 4 In some embodiments, R 3c -CH 3 In some embodiments, each R 3c is hydrogen or -CH 3 In some embodiments, R 3c is optionally substituted aryl. In some embodiments, R 3c is optionally substituted phenyl.

[0133] In some embodiments, D is -S(=O) 2 OR 9a OR -C(=O)OR 9a In some embodiments, D is -S(=O) 2 OR 9a In some embodiments, D is -C(=O)OR 9a In some embodiments, R 9a is hydrogen or -CH 3 In some embodiments, R 9a is hydrogen. In some embodiments, R 9a -CH 3 It is.

[0134] In some embodiments, D is -S(=O) 2 O - or -C(=O)O - In some embodiments, D is -S(=O) 2 O - In some embodiments, D is -C(=O)O - It is.

[0135] In some embodiments, E is -NR 9a R 9b R 9c+ or -S(=O) 2 OR 9a In some embodiments, E is -NR9a R 9b R 9c+ OR -C(=O)OR 9a It is.

[0136] In some embodiments, E is -NR 9a R 9b R 9c+ In some embodiments, each R 9a , R 9b , and R 9c are independently hydrogen or C 1 -C 4 In some embodiments, each R 9a , R 9b , and R 9c are independently hydrogen or -CH 3 In some embodiments, R 9a is hydrogen. In some embodiments, R 9a -CH 3 In some embodiments, R 9b is hydrogen. In some embodiments, R 9b -CH 3 In some embodiments, R 9c is hydrogen. In some embodiments, R 9c -CH 3 It is.

[0137] In some embodiments, E is -S(=O) 2 OR 9a In some embodiments, E is -C(=O)OR 9a In some embodiments, each R 9a is hydrogen or -CH 3 In some embodiments, R 9a is hydrogen. In some embodiments, R 9a -CH 3 It is.

[0138] In some embodiments, E is -S(=O) 2 O - or -C(=O)O -In some embodiments, E is -S(=O) 2 O - In some embodiments, E is -C(=O)O - It is.

[0139] In some embodiments, each R 3a and R 3b are independently hydrogen or C 1 -C 4 In some embodiments, each R 3a and R 3b are independently hydrogen or -CH 3 In some embodiments, each R 3a and R 3b is hydrogen. In some embodiments, each R 3a and R 3b -CH 3 It is.

[0140] In some embodiments, each R 4c and R 4d are independently hydrogen and -CH 3 In some embodiments, each R 4c and R 4d is hydrogen.

[0141] In some embodiments, each R 5d and R 5e are independently hydrogen and -CH 3 In some embodiments, each R 5d and R 5e is hydrogen.

[0142] In some embodiments, each R 4c , R 4d , R 5d , and R 5e are independently hydrogen or -CH 3 In some embodiments, each R 4c , R 4d , R 5d , and R 5eis hydrogen. In some embodiments, each R 4c , R 4d , R 5d , and R 5e -CH 3 It is.

[0143] In some embodiments, each R 6c and R 6d are independently hydrogen and -CH 3 In some embodiments, each R 6c and R 6d is hydrogen. In some embodiments, each R 6c and R 6d -CH 3 It is.

[0144] In some embodiments, each R 3c and R 3d are independently hydrogen and -CH 3 In some embodiments, each R 3c and R3 d is hydrogen.

[0145] In some embodiments, each R 3c , R 3d , R 6c , and R 6d are independently hydrogen or -CH 3 In some embodiments, each R 3c , R 3d , R 6c , and R 6d is hydrogen. In some embodiments, each R 3c , R 3d , R 6c , and R 6d -CH 3 It is.

[0146] In some embodiments, R 11a is hydrogen or -CH 3 In some embodiments, R 11a is hydrogen. In some embodiments, R 11a -CH3 It is.

[0147] In some embodiments, R 12a is hydrogen or -CH 3 In some embodiments, R 12a is hydrogen. In some embodiments, R 12a -CH 3 It is.

[0148] In some embodiments, R 13a is hydrogen or -CH 3 In some embodiments, R 13a is hydrogen. In some embodiments, R 13a -CH 3 It is.

[0149] In some embodiments, each R 11a , R 12a , and R 13a are independently hydrogen or -CH 3 In some embodiments, each R 11a , R 12a , and R 13a is hydrogen. In some embodiments, each R 11a , R 12a , and R 13a -CH 3 It is.

[0150] In some embodiments, each R 11b , R 11c , R 12b , R 12c , R 13b , and R 13c is hydrogen.

[0151] In some embodiments, n is 0, 1, 2, 3, 4, 5, or 6. In some embodiments, n is 0, 1, 2, 3, 4, or 5. In some embodiments, n is 0, 1, or 2. In some embodiments, n is 0. In some embodiments, n is 1. In some embodiments, n is 2. In some embodiments, n is 3. In some embodiments, n is 4. In some embodiments, n is 5.

[0152] In some embodiments, s is 1, 2, 3, or 4. In some embodiments, s is 1. In some embodiments, s is 2. In some embodiments, s is 3. In some embodiments, s is 4.

[0153] In some embodiments, t is 1, 2, 3, or 4. In some embodiments, t is 1. In some embodiments, t is 2. In some embodiments, t is 3. In some embodiments, t is 4.

[0154] In some embodiments, p is 1, 2, 3, or 4. In some embodiments, p is 1. In some embodiments, p is 2. In some embodiments, p is 3. In some embodiments, p is 4.

[0155] In some embodiments, k is 1, 2, 3, 4, or 5. In some embodiments, k is 1, 2, 3, or 4. In some embodiments, k is 2, 3, or 4. In some embodiments, k is 2 or 3. In some embodiments, k is 1. In some embodiments, k is 2. In some embodiments, k is 3. In some embodiments, k is 4.

[0156] In some embodiments, each s, t, p, and k is independently 1, 2, or 3. In some embodiments, each s, t, p, and k is independently 1 or 2. In some embodiments, each s, t, p, and k is independently 2 or 3.

[0157] In some embodiments, the repeat unit of formula (IX) comprises a positively charged repeat unit of formula (IX). In some embodiments, the repeat unit of formula (IX) comprises a negatively charged repeat unit of formula (IX). In some embodiments, the copolymer comprising repeat units of formulas (VII), (VIII), and (IX) comprises a positively charged repeat unit of formula (IX) and a negatively charged repeat unit of formula (IX). In some embodiments, the ratio of the positively charged repeat unit of formula (IX) to the negatively charged repeat unit of formula (IX) in the copolymer comprising repeat units of formulas (VII), (VIII), and (IX) is about 10:1 to about 1:10. In some embodiments, the ratio of the positively charged repeat unit of formula (IX) to the negatively charged repeat unit of formula (IX) in the copolymer comprising repeat units of formulas (VII), (VIII), and (IX) is about 5:1 to about 1:5. In some embodiments, the ratio of positively charged repeat units of formula (IX) to negatively charged repeat units of formula (IX) in a copolymer comprising repeat units of formula (VII), (VIII), and (IX) is about 2:1 to about 1:2. In some embodiments, the ratio of positively charged repeat units of formula (IX) to negatively charged repeat units of formula (IX) in a copolymer comprising repeat units of formula (VII), (VIII), and (IX) is about 1:1.

[0158] In some embodiments, a copolymer comprising repeat units of formula (VII), (VIII), and (IX) comprises the following number of monomer units: [(Formula (VII))a(Formula (VIII))b(Formula (IX))c], where each number a, b, and c is independently selected from 1 to 1000. In some embodiments, each number a, b, and c is independently selected from 1 to 100.

[0159] In some embodiments, a is 1 to 10. In some embodiments, a is 5 to 10. In some embodiments, a is 5 to 20. In some embodiments, a is at least 1, at least 2, at least 3, at least 4, at least 5, at least 6, at least 7, at least 8, at least 9, at least 10, at least 12, at least 15, or at least 20. In some embodiments, a is up to 1, up to 2, up to 3, up to 4, up to 5, up to 6, up to 7, up to 8, up to 9, up to 10, up to 12, up to 15, or up to 20.

[0160] In some embodiments, b is 5 to 75. In some embodiments, b is 10 to 100. In some embodiments, b is 20 to 250. In some embodiments, b is 50 to 500. In some embodiments, b is 100 to 1000. In some embodiments, b is at least 1, at least 5, at least 10, at least 25, at least 50, at least 100, at least 200, at least 300, at least 400, at least 500, at least 600, at least 700, at least 800, at least 900, or at least 1000. In some embodiments, b is up to 1, up to 5, up to 10, up to 25, up to 50, up to 100, up to 200, up to 300, up to 400, up to 500, up to 600, up to 700, up to 800, up to 900, or up to 1000.

[0161] In some embodiments, c is 5 to 75. In some embodiments, c is 10 to 100. In some embodiments, c is 20 to 250. In some embodiments, c is 50 to 500. In some embodiments, c is 100 to 1000. In some embodiments, c is at least 1, at least 5, at least 10, at least 25, at least 50, at least 100, at least 200, at least 300, at least 400, at least 500, at least 600, at least 700, at least 800, at least 900, or at least 1000. In some embodiments, c is up to 1, up to 5, up to 10, up to 25, up to 50, up to 100, up to 200, up to 300, up to 400, up to 500, up to 600, up to 700, up to 800, up to 900, or up to 1000.

[0162] In some embodiments, the ratio of (b+c) to a is 1:1000 to 1000:1. In some embodiments, the ratio of (b+c) to a is 1:100 to 100:1. In some embodiments, the ratio of (b+c) to a is 1:10 to 10:1. In some embodiments, the ratio of (b+c) to a is about 5:1, about 10:1, about 20:1, about 30:1, about 40:1, about 50:1, about 75:1, about 100:1, about 250:1, about 500:1, about 750:1, or about 1000:1.

[0163] In some embodiments, the different variables of the compounds of formula (I), formula (II), formula (III), formula (VII), formula (VIII), and formula (IX) above are applicable to the corresponding formulas, compositions, films, devices, etc. disclosed throughout this application.

[0164] Any combination of the groups described above or below for the various variables is contemplated herein. Throughout the specification, groups and substituents thereof are chosen by one of ordinary skill in the art to provide stable moieties and compounds.

[0165] Further forms of the compound In one aspect, the compounds of formula (I), (II), (III), (IV), (V), or (VI), or copolymers comprising repeat units of formula (VII), (VIII), and (IX), have one or more stereocenters, each of which independently exists in either the R or S configuration. The compounds provided herein include all diastereomeric, enantiomeric, and epimeric forms, and appropriate mixtures thereof. The compounds and methods provided herein include all cis, trans, syn, anti, entgegen (E), and zusammen (Z) isomers, and appropriate mixtures thereof. In certain embodiments, the compounds described herein are prepared as their individual stereoisomers by reacting a racemic mixture of the compound with an optically active resolving agent to form a pair of diastereomeric compounds / salts, separating the diastereomers, and recovering the optically pure enantiomers. In some embodiments, the resolution of the enantiomers is carried out using covalent diastereomeric derivatives of the compounds described herein. In another embodiment, the diastereomers are separated by separation / resolution techniques based on differences in solubility. In other embodiments, separation of stereoisomers is carried out by chromatography, or by forming diastereomeric salts and separating by recrystallization or chromatography, or any combination thereof. Jean Jacques, Andre Collet, Samuel H. Wilen, "Enantiomers, Racemates and Resolutions", John Wiley And Sons, Inc., 1981. In one aspect, stereoisomers are obtained by stereoselective synthesis.

[0166] In another embodiment, the compounds described herein are isotopically (e.g., with a radioisotope) or by other means, including, but not limited to, the use of chromophores or fluorescent moieties, bioluminescent labels, or chemiluminescent labels.

[0167] The compounds described herein include compounds that are identical to the compounds listed in the various formulas and structures presented herein, but are isotopically labeled due to the fact that one or more atoms are replaced with an atom having an atomic mass or mass number different from the atomic mass or mass number normally found in nature. Examples of isotopes that can be incorporated into the compounds include isotopes of hydrogen, carbon, nitrogen, oxygen, sulfur, fluorine, and chlorine, e.g., 2 H, 3 H, 13 C. 14 C. 15 N, 18 O. 17 O. 35 S, 18 F, 36 In one embodiment, the isotopically labeled compounds described herein, e.g., 3 H and 14 Compounds incorporating a radioactive isotope such as C are useful in drug and / or substrate tissue distribution assays. In one aspect, substitution with isotopes such as deuterium provides certain therapeutic advantages resulting, for example, from greater metabolic stability, such as increased in vivo half-life or reduced dosage requirements.

[0168] The compounds described herein may be formed and / or used as salts. Types of salts include: (1) salts of the free base form of the compound with inorganic acids such as hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid, metaphosphoric acid, and the like, or with organic acids such as acetic acid, propionic acid, hexanoic acid, cyclopentanepropionic acid, glycolic acid, pyruvic acid, lactic acid, malonic acid, succinic acid, malic acid, maleic acid, fumaric acid, trifluoroacetic acid, tartaric acid, citric acid, benzoic acid, 3-(4-hydroxybenzoyl)benzoic acid, cinnamic acid, mandelic acid, methanesulfonic acid, ethanesulfonic acid, 1,2-ethanedisulfonic acid, 2-hydroxyethanesulfonic acid, benzenesulfonic acid, toluenesulfonic acid, 2-naphthalenesulfonic acid, 4-methylbicyclo-[2.2.2]oct-2-ene-1-carboxylic acid, and the like. , glucoheptonic acid, 4,4'-methylenebis(3-hydroxy-2-ene-1-carboxylic acid), 3-phenylpropionic acid, trimethylacetic acid, tertiary butylacetic acid, lauryl sulfuric acid, gluconic acid, glutamic acid, hydroxynaphthoic acid, salicylic acid, stearic acid, muconic acid, butyric acid, phenylacetic acid, phenylbutyric acid, valproic acid, and the like; (2) salts formed when an acidic proton present in the parent compound is replaced with a metal ion, such as an alkali metal ion (e.g., lithium, sodium, potassium), an alkaline earth ion (e.g., magnesium or calcium), or an aluminum ion. In some cases, the compounds described herein may be prepared with organic bases, such as, but not limited to, ethanolamine, diethanolamine, triethanolamine, tromethamine, N-methylglucamine, dicyclohexylamine, tris(hydroxymethyl)methylamine, and the like. In other cases, the compounds described herein may form salts with amino acids, such as, but not limited to, arginine, lysine, and the like. Acceptable inorganic bases used to form salts with compounds containing acidic protons include, but are not limited to, aluminum hydroxide, calcium hydroxide, potassium hydroxide, sodium carbonate, sodium hydroxide, and the like.

[0169] Reference to salt should be understood to include solvent addition forms, particularly solvates. Solvates contain either stoichiometric or non-stoichiometric amounts of solvent, such as water, ethanol, etc. Hydrates are formed when the solvent is water, or alcoholates are formed when the solvent is alcohol. Solvates of the compounds described herein can be conveniently prepared or formed during the processes described herein. In addition, the compounds provided herein can exist in unsolvated and solvated forms. In general, solvated forms are considered equivalent to unsolvated forms for the purposes of the compounds and methods provided herein.

[0170] Compound synthesis The compounds described herein are synthesized using standard synthetic techniques or using methods known in the art in combination with the methods described herein.

[0171] Unless otherwise indicated, conventional methods of mass spectroscopy, NMR, HPLC, protein chemistry, biochemistry, recombinant DNA techniques and pharmacology are employed.

[0172] The compounds are prepared using standard organic chemistry techniques, for example, as described in March's Advanced Organic Chemistry, 6th Edition, John Wiley and Sons, Inc. Alternative reaction conditions for the synthetic transformations described herein, such as variations in solvents, reaction temperatures, reaction times, as well as different chemical reagents and other reaction conditions, may be used. The starting materials are available from commercial sources or are readily prepared.

[0173] Suitable references and papers detailing the synthesis of reactants useful in the preparation of the compounds described herein or providing references to articles describing the preparation include, for example, "Synthetic Organic Chemistry", John Wiley & Sons, Inc., New York; S.R. Sandler et al., "Organic Functional Group Preparations," 2nd Ed., Academic Press, New York, 1983; H.O. House, "Modern Synthetic Reactions", 2nd Ed., W.A. Benjamin, Inc. Menlo Park, Calif. 1972; T.L. Gilchrist, "Heterocyclic Chemistry", 2nd Ed., John Wiley & Sons, New York, 1992; J. March, "Advanced Organic Chemistry: Reactions, Mechanisms and Structure", 4th Ed., Wiley Interscience, New York, 1992. Further suitable references and papers detailing the synthesis of reactants useful for the preparation of the compounds described herein or providing references to articles describing the preparation include, for example, Fuhrhop, J. and Penzlin G. "Organic Synthesis: Concepts, Methods, Starting Materials", Second, Revised and Enlarged Edition (1994) John Wiley & Sons ISBN: 3 527-29074-5; Hoffman, RV "Organic Chemistry, An Intermediate Text" (1996) Oxford University Press, ISBN 0-19-509618-5; Larock, RC "Comprehensive Organic Transformations: A Guide to Functional Group Preparations" 2nd Edition (1999) Wiley-VCH, ISBN: 0-471-19031-4; March, J.“Advanced Organic Chemistry: Reactions, Mechanisms, and Structure” 4th Edition (1992) John Wiley&Sons, ISBN:0-471-60180-2, Otera, J. (editor) “Modern Carbonyl Chemistry” (2000) Wiley-VCH, ISBN: 3-527-29871-1, Patai, S. “Patai's 1992 Guide to the Chemistry of Functional Groups” (1992) Interscience ISBN: 0-471-93022-9, Solomons, TWG “Organic Chemistry” 7th Edition (2000) John Wiley & Sons, ISBN: 0-471-19095-0, Stowell, JC, “Intermediate Organic Chemistry” 2nd Edition (1993) Wiley-Interscience, ISBN: 0-471-57456-2, “Industrial Organic Chemicals: Starting Materials and Intermediates: An Ullmann's Encyclopedia” (1999) John Wiley & Sons, ISBN: 3-527-29645-X (8 volumes in total), “Organic Reactions” (1942-2000) John Wiley & Sons (55 volumes or more), and “Chemistry of Functional Groups” John Wiley & Sons (73 volumes in total).

[0174] In the reactions described, it may be necessary to protect reactive functional groups, such as hydroxy, amino, imino, thio, or carboxy groups (if these are desired in the final product), to avoid undesired participation in the reaction.Detailed descriptions of the techniques applicable to the creation and removal of protective groups are described in Greene and Wuts, Protective Groups in Organic Synthesis, 3rd Ed., John Wiley&Sons, New York, NY, 1999 and Kocienski, Protective Groups, Thieme Verlag, New York, NY, 1994 (which are incorporated herein by reference for such disclosure).

[0175] In some embodiments, the compounds are synthesized as described in the Examples section.

[0176] II. Anti-biofouling coatings In one aspect, described herein is an anti-biofouling coating comprising a compound of formula (I): [ka] During the ceremony, A is -C(=O)-, -S(=O)-, -S(=O) 2 - and -S(=O)(-NR 3 )- is selected from L is -OQ, -NR 3 Q, and -N(R 3 ) 2 Q + is selected from Q is a structure represented by the following formula: [ka] Z is -CR 6a R 6b -, -C(=O)-, -C(=NH)-, and -C(=NH)NR 7 - selected from m is an integer selected from 0, 1, 2, 3, 4, 5, 6, 7, and 8; Each R 1a and R 1b is independently selected from hydrogen and halogen; Each R 2a and R 2b are independently selected from halogen, -CN, and optionally substituted C 1 -C 6 fluoroalkyl; Each R 3 are independently hydrogen, optionally substituted C 1 -C 4 Alkyl, -X-optionally substituted C 1 -C 4 selected from alkyl, optionally substituted aryl, and -X-optionally substituted aryl; X is -C(=O)-, -S(=O)-, or -S(=O) 2 - and Each R 4a , R 4b , R 5a , R 5c , R 6a , and R 6b are independently hydrogen, halogen, -CN, -OR 9 , optionally substituted C 1 -C 4 Alkyl, optionally substituted C 1 -C 4 Fluoroalkyl, optionally substituted aryl, -NR 8a R 8b , -NR 8a R 8b R 8c+ , -S(=O) 2 O - , -S(=O) 2 OR 9 , -C(=O)O - , and -C(=O)OR 9 is selected from R 5b -OR 10b , -NR 10a R 10b , or -NR 10a R 10b R 10c+ and Each R 7 , R 8a , R 8b , R 8c , and R 9 are independently hydrogen and optionally substituted C 1 -C 4 selected from alkyl and optionally substituted aryl; Each R 10a and R 10c are independently hydrogen, optionally substituted C 1 -C 4 Alkyl, optionally substituted aryl, -(optionally substituted C 1 -C 8 Alkylene)S(=O) 2 O - , -(optionally substituted C 1 -C 8 Alkylene)S(=O) 2 OH, -(optionally substituted C 1 -C 8 Alkylene)C(=O)O - , and -(optionally substituted C 1 -C 8 alkylene)C(=O)OH; R 10b is -C(=O)-C 2 -C 6 Alkenyl, -S(=O)-C 2 -C 6 Alkenyl, or -S(=O) 2 -C 2 -C 6 It is alkenyl.

[0177] In some embodiments, the compound of formula (I) is N-(2-((4-azido-2,3,5,6-tetrafluorophenyl)sulfonamido)ethyl)methacrylamide, N-(2-acrylamidoethyl)-4-azido-2,3,5,6-tetrafluorobenzamide, or Not 2-(methacryloyloxy)ethyl 4-azido-2,3,5,6-tetrafluorobenzoate.

[0178] In some embodiments, the anti-biofouling coating comprising a compound of formula (I) comprises a residue of a compound of formula (I). In some embodiments, the residue of a compound of formula (I) comprises a singlet nitrene residue.

[0179] In some embodiments, the compound of formula (I) has the structure above.

[0180] In some embodiments, the different variables of the compound of formula (I) are as described above.

[0181] In some embodiments, the compound of formula (I) has the structure of formula (Ia), (Ib), (Ic), (Id), (Ie), (If), (Ig), or (Ih) above.

[0182] In some embodiments, the compound of formula (I) is selected from the compounds described above.

[0183] In another aspect, described herein is an anti-biofouling coating comprising a compound of formula (II): [ka] During the ceremony, Each R 1a and R 1b is independently selected from hydrogen and halogen; Each R 2a and R 2b are independently selected from halogen, -CN, and optionally substituted C 1 -C 6 fluoroalkyl; Each A 1 , A 2 , and A 3 are independently -C(=O)-, -S(=O)-, -S(=O) 2 - and -S(=O)(=NR 3c )- is selected from Each B 1 , B 2 , and B.3 are independently -O- and -NR 3c - selected from D is -S(=O) 2 O - , -S(=O) 2 OR 9a , -C(=O)O - , or -C(=O)OR 9a and Z 1 is -(CR 6c R 6d ) s - and Z 2 is -(CR 6c R 6d ) t - and Z 3 is -(CR 6c R 6d ) p - and Each R 3a and R 3b are independently hydrogen, optionally substituted C 1 -C 4 alkyl, and optionally substituted benzyl; Each R 4c , R 4d , R 5d , R 5e , R 6c , and R 6d are independently hydrogen, halogen, -CN, -OR 9a , optionally substituted C 1 -C 4 Alkyl, optionally substituted C 1 -C 4 Fluoroalkyl, optionally substituted C 2 -C 6 Alkenyl, -NR 3c R 3d , -S(=O) 2 O - , -S(=O) 2 OR 9a , -C(=O)O - , and -C(=O)OR 9a is selected from Each R3c and R 3d are independently hydrogen, optionally substituted C 1 -C 4 Alkyl, -X-optionally substituted C 1 -C 4 Alkyl, optionally substituted C 2 -C 6 alkenyl, and optionally substituted aryl; X is -C(=O)-, -S(=O)-, or -S(=O) 2 - and Each R 9a , R 11a , R 11b , R 11c , R 12a , R 12b , and R 12c are independently hydrogen, optionally substituted C 1 -C 4 alkyl, and optionally substituted aryl; n is an integer selected from 0, 1, 2, 3, 4, 5, 6, 7, and 8; s is an integer selected from 1, 2, 3, 4, or 5; t is an integer selected from 1, 2, 3, 4, or 5; p is an integer selected from 1, 2, 3, 4, or 5; 0 <x<1であり、 The compounds of formula (II) are charged or zwitterionic.

[0184] In some embodiments, the compound of formula (II) is [ka] isn't it.

[0185] In some embodiments, x in formula (II) is not about 0.9434.

[0186] In some embodiments, the compound of formula (II) is not obtained by using 2 g of sulfobetaine methacrylate monomer and 156 mg of perfluorophenyl azide methacrylamide monomer.

[0187] In some embodiments, the different variables of the compound of formula (II) are as described above.

[0188] In another aspect, described herein is an anti-biofouling coating comprising a compound of formula (III): [ka] During the ceremony, Each R 1a and R 1b is independently selected from hydrogen and halogen; Each R 2a and R 2b are independently selected from halogen, -CN, and optionally substituted C 1 -C 6 fluoroalkyl; Each A 1 , A 2 , and A 3 are independently -C(=O)-, -S(=O)-, -S(=O) 2 - and -S(=O)(=NR 3c )- is selected from Each B 1 , B 2 , and B. 3 are independently -O- and -NR 3c - selected from Z 1 is -(CR 6c R 6d ) s - and Z 2 is -(CR 6c R 6d ) t - and E is -CN, -OR 9a , -NR 9a R 9b , -NR 9a R9b R 9c+ , optionally substituted C 1 -C 4 Alkyl, optionally substituted C 1 -C 6 Fluoroalkyl, -S(=O) 2 O - , -S(=O) 2 OR 9a , -C(=O)O - , or -C(=O)OR 9a and Each R 4c , R 4d , R 5d , R 5e , R 6c , and R 6d are independently hydrogen, halogen, -CN, -OR 9a , optionally substituted C 1 -C 4 Alkyl, optionally substituted C 1 -C 4 Fluoroalkyl, optionally substituted C 2 -C 6 Alkenyl, -NR 3c R 3d , -S(=O) 2 O - , -S(=O) 2 OR 9a , -C(=O)O - , and -C(=O)OR 9a is selected from Each R 3c and R 3d are independently hydrogen, optionally substituted C 1 -C 4 Alkyl, -X-optionally substituted C 1 -C 4 Alkyl, optionally substituted C 2 -C 6 alkenyl, and optionally substituted aryl; X is -C(=O)-, -S(=O)-, or -S(=O) 2 - and Each R 9a , R 9b , R9c , R 11a , R 11b , R 11c , R 12a , R 12b , and R 12c are independently hydrogen, optionally substituted C 1 -C 4 alkyl, and optionally substituted aryl; n is an integer selected from 0, 1, 2, 3, 4, 5, 6, 7, and 8; s is an integer selected from 1, 2, 3, 4, or 5; t is an integer selected from 1, 2, 3, 4, or 5; 0 <x<1である。

[0189] In some embodiments, the compound of formula (III) is charged or zwitterionic. In some embodiments, the compound of formula (III) comprises a positively charged repeat unit. In some embodiments, the compound of formula (III) comprises a negatively charged repeat unit. In some embodiments, the compound of formula (III) comprises a positively charged repeat unit and a negatively charged repeat unit. In some embodiments, the ratio of the positively charged repeat unit to the negatively charged repeat unit in the compound of formula (III) is about 10:1 to about 1:10. In some embodiments, the ratio of the positively charged repeat unit to the negatively charged repeat unit in the compound of formula (III) is about 5:1 to about 1:5. In some embodiments, the ratio of the positively charged repeat unit to the negatively charged repeat unit in the compound of formula (III) is about 2:1 to about 1:2. In some embodiments, the ratio of the positively charged repeat unit to the negatively charged repeat unit in the compound of formula (III) is about 1:1.

[0190] In some embodiments, the different variables of the compound of formula (III) are as described above.

[0191] In another aspect, described herein is an anti-biofouling coating comprising a copolymer, the coating comprising: a) a repeating unit of formula (VII): [ka] (In the formula, Each R 1a and R 1b is independently selected from hydrogen and halogen; Each R 2a and R 2b are independently selected from halogen, -CN, and optionally substituted C 1 -C 6 fluoroalkyl; Each A 1 and A 2 are independently -C(=O)-, -S(=O)-, -S(=O) 2 - and -S(=O)(=NR 3c )- is selected from Each B 1 and B. 2 are independently -O- and -NR 3c - selected from Z 1 is -(CR 6c R 6d ) s - and Each R 4c , R 4d , R 5d , R 5e , R 6c , and R 6d are independently hydrogen, halogen, -CN, -OR 9a , optionally substituted C 1 -C 4 Alkyl, optionally substituted C 1 -C 4 Fluoroalkyl, optionally substituted C 2 -C 6 Alkenyl, -NR 3c R 3d , -S(=O) 2 O - , -S(=O) 2 OR 9a , -C(=O)O - , and -C(=O)OR 9a is selected from Each R 3c and R3d are independently hydrogen, optionally substituted C 1 -C 4 Alkyl, -X-optionally substituted C 1 -C 4 Alkyl, optionally substituted C 2 -C 6 alkenyl, and optionally substituted aryl; X is -C(=O)-, -S(=O)-, or -S(=O) 2 - and Each R 9a , R 11a , R 11b , and R 11c are independently hydrogen, optionally substituted C 1 -C 4 alkyl, and optionally substituted aryl; n is an integer selected from 0, 1, 2, 3, 4, 5, 6, 7, and 8; s is an integer selected from 1, 2, 3, 4, and 5; b) A repeating unit of formula (VIII): [ka] (In the formula, A 3 -C(=O)-, -S(=O)-, -S(=O) 2 - or -S(=O)(=NR 3c )-and B 3 is -O- or -NR 3c - and D is -S(=O) 2 O - , -S(=O) 2 OR 9a , -C(=O)O - , or -C(=O)OR 9a and Z 2 is -(CR 6c R 6d ) t - and Z 3 is -(CR6c R 6d ) p - and Each R 3a and R 3b are independently hydrogen, optionally substituted C 1 -C 4 alkyl, and optionally substituted benzyl; Each R 6c and R 6d are independently hydrogen, halogen, -CN, -OR 9a , optionally substituted C 1 -C 4 Alkyl, optionally substituted C 1 -C 4 Fluoroalkyl, optionally substituted C 2 -C 6 Alkenyl, -NR 3c R 3d , -S(=O) 2 O - , -S(=O) 2 OR 9a , -C(=O)O - , and -C(=O)OR 9a is selected from Each R 3c and R 3d are independently hydrogen, optionally substituted C 1 -C 4 Alkyl, -X-optionally substituted C 1 -C 4 Alkyl, optionally substituted C 2 -C 6 alkenyl, and optionally substituted aryl; X is -C(=O)-, -S(=O)-, or -S(=O) 2 - and Each R 9a , R 12a , R 12b , and R 12c are independently hydrogen, optionally substituted C 1 -C 4 alkyl, and optionally substituted aryl; t is an integer selected from 1, 2, 3, 4, or 5; p is an integer selected from 1, 2, 3, 4, or 5; A repeat unit of formula (VIII), wherein the repeat unit of formula (VIII) is charged or zwitterionic; c) A repeating unit of formula (IX): [ka] (A 4 -C(=O)-, -S(=O)-, -S(=O) 2 - or -S(=O)(=NR 3c )-and B 4 is -O- or -NR 3c - and Z 4 is -(CR 6c R 6d ) k - and E is -CN, -OR 9a , -NR 9a R 9b , -NR 9a R 9b R 9c+ , optionally substituted C 1 -C 4 Alkyl, optionally substituted C 1 -C 6 Fluoroalkyl, -S(=O) 2 O - , -S(=O) 2 OR 9a , -C(=O)O - , or -C(=O)OR 9a and Each R 6c and R 6d are independently hydrogen, halogen, -CN, -OR 9a , optionally substituted C 1 -C 4 Alkyl, optionally substituted C 1 -C 4 Fluoroalkyl, optionally substituted C 2 -C 6 Alkenyl, -NR3c R 3d , -S(=O) 2 O - , -S(=O) 2 OR 9a , -C(=O)O - , and -C(=O)OR 9a is selected from Each R 3c and R 3d are independently hydrogen, optionally substituted C 1 -C 4 Alkyl, -X-optionally substituted C 1 -C 4 Alkyl, optionally substituted C 2 -C 6 alkenyl, and optionally substituted aryl; X is -C(=O)-, -S(=O)-, or -S(=O) 2 - and Each R 9a , R 9b , R 9c , R 13a , R 13b , and R 13c are independently hydrogen, optionally substituted C 1 -C 4 alkyl, and optionally substituted aryl; and k is an integer selected from 1 to 10.

[0192] In some embodiments, the recurring unit of formula (IX) is charged or zwitterionic.

[0193] In some embodiments, the different variables of the compounds of formula (VII), formula (VIII), and formula (IX) are as described above.

[0194] Any combination of the groups described above or below for the various variables is contemplated herein. Throughout the specification, groups and substituents thereof are chosen by one of ordinary skill in the art to provide stable moieties and compounds.

[0195] In some embodiments, the anti-biofouling coatings described herein comprise one or more compounds of formula (I), (II), or (III).

[0196] In some embodiments, the anti-biofouling coatings described herein comprise one or more copolymers of formula (II) or (III). In some embodiments, the anti-biofouling coatings described herein comprise one or more copolymers comprising repeat units of formula (VII), (VIII), and (IX).

[0197] In some embodiments, an anti-biofouling coating comprising one or more compounds of formula (I), (II), and (III) is applied onto the surface of the device. In some embodiments, an anti-biofouling coating comprising one or more copolymers comprising repeating units of formula (VII), (VIII), and (IX) is applied onto the surface of the device. In some embodiments, the surface of the device comprises a polymer. In some embodiments, the polymer is selected from polysiloxane, polyurethane, polyamide, polyimide, epoxy resin, polyester, polyolefin, polysulfone, polycarbonate, polyvinyl chloride, polyvinylidene fluoride, polyether, polyether terphthalate, or mixtures thereof.

[0198] III. Devices In certain embodiments, provided herein is a device coated with one or more compounds as described herein. In some embodiments, the device is a medical device. In some embodiments, the device is a non-medical device. In some cases, provided herein is a medical device coated with one or more compounds as described herein. In other cases, provided herein is a non-medical device coated with one or more compounds as described herein. In further cases, provided herein is a device coated with one or more compounds as described herein, the coated device reduces the possibility of infection.

[0199] In some embodiments, the device comprises a polymer-based device. In some embodiments, the polymer-based device comprises a polyolefinic device. In some embodiments, the polyolefinic device comprises a device modified with polyethylene (PE), polypropylene (PP), polyamide (PA), polytetrafluoroethylene (PTFE), polyvinylidene fluoride (PVdF), polyvinyl chloride (PVC), or combinations thereof. In some embodiments, the device comprises a microporous device or a non-woven device. In some embodiments, the device comprises a carbon-based device comprising a moiety capable of binding with a compound having a structure of formula (I), (II), or (III). In some embodiments, the device comprises a carbon-based device comprising a moiety capable of binding with a copolymer comprising repeat units of formula (VII), (VIII), and (IX). In some embodiments, the carbon-based device comprises a polymeric moiety. In some embodiments, the carbon-based device comprises a carbon-based polymer. In some embodiments, the carbon-based device comprises a polyolefinic moiety. In some embodiments, the polyolefin portion comprises a polyethylene (PE) portion, a polypropylene (PP) portion, a polyamide (PA) portion, a polytetrafluoroethylene (PTFE) portion, a polyvinylidene fluoride (PVdF) portion, or a polyvinyl chloride (PVC) portion.

[0200] In some embodiments, the device comprises a carbon-based device. In some embodiments, the carbon-based device comprises a carbon-based polymer. In some embodiments, the carbon-based device comprises a polyolefin portion. In some embodiments, the polyolefin portion comprises a polyethylene portion, a polypropylene portion, a polyvinyl chloride portion, a polyvinylidene fluoride portion, a polytetrafluoroethylene portion, a polychlorotrifluoroethylene portion, or a polystyrene portion. In some embodiments, the carbon-based polymer comprises a polyamide portion, a polyurethane portion, a phenol-formaldehyde resin portion, a polycarbonate portion, a polychloroprene portion, a polyacrylonitrile portion, a polyimide portion, or a polyester portion. In some embodiments, the carbon-based polymer comprises nylon. In some embodiments, the carbon-based polymer comprises polyethylene terephthalate.

[0201] In some embodiments, the device comprises a silicon-based device. In some embodiments, the silicon-based device comprises a silicon-based polymer portion. In some embodiments, the device comprises a silicon-based device comprising a portion capable of bonding with a compound having the structure of formula (I), (II), or (III). In some embodiments, the device comprises a silicon-based device comprising a portion capable of bonding with a copolymer comprising repeating units of formula (VII), (VIII), and (IX). In some embodiments, the silicon-based device comprises a polymer portion. In some embodiments, the silicon-based device comprises a siloxane polymer portion, a sesquisiloxane polymer portion, a siloxane-silarylene polymer portion, a silakylene polymer portion, a polysilane portion, a polysilylene portion, or a polysilazane portion.

[0202] In some embodiments, the silicon based device comprises a siloxane polymer portion. In some embodiments, the silicon based device comprises a silicone polymer. In some embodiments, the silicon based device comprises a silicone based device.

[0203] In some embodiments, the device comprises a carbon-based device or a silicon-based device.

[0204] In some embodiments, the devices described herein coated with the compounds described herein provide a reduced likelihood of infection compared to devices not coated with the compounds. In some cases, the reduced likelihood of infection is about 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80%, 90%, 95%, 99%, 99.5%, 99.9% or more compared to devices not coated with the compounds. In some cases, the reduced likelihood of infection is about 10% or more compared to devices not coated with the compounds. In some cases, the reduced likelihood of infection is about 20% or more compared to devices not coated with the compounds. In some cases, the reduced likelihood of infection is about 30% or more compared to devices not coated with the compounds. In some cases, the reduced likelihood of infection is about 40% or more compared to devices not coated with the compounds. In some cases, the reduced likelihood of infection is about 50% or more compared to devices not coated with the compounds. In some cases, the reduction in the likelihood of infection is about 60% or more compared to a device not coated with the compound. In some cases, the reduction in the likelihood of infection is about 70% or more compared to a device not coated with the compound. In some cases, the reduction in the likelihood of infection is about 80% or more compared to a device not coated with the compound. In some cases, the reduction in the likelihood of infection is about 90% or more compared to a device not coated with the compound. In some cases, the reduction in the likelihood of infection is about 95% or more compared to a device not coated with the compound. In some cases, the reduction in the likelihood of infection is about 99% or more compared to a device not coated with the compound.In some cases, the reduction in the likelihood of infection is about 99.5% or more compared to a device that is not coated with the compound. In some cases, the reduction in the likelihood of infection is about 99.9% or more compared to a device that is not coated with the compound.

[0205] Medical Devices In some embodiments, the devices described herein are medical devices. In some cases, the medical devices described herein include dental instruments or medical instruments. In some cases, the medical devices include implants, IVs, prostheses, suture material, valves, stents, catheters, rods, shunts, scopes, contact lenses, tubing, wires, electrodes, clips, fasteners, syringes, containers, or combinations thereof. In some embodiments, the medical device includes an implant. In some embodiments, the medical device includes an IV. In some embodiments, the medical device includes a prosthesis. In some embodiments, the medical device includes suture material. In some embodiments, the medical device includes a valve. In some embodiments, the medical device includes a stent. In some embodiments, the medical device includes a catheter. In some embodiments, the medical device includes a rod. In some embodiments, the medical device includes a shunt. In some embodiments, the medical device includes a scope. In some embodiments, the medical device includes a contact lens. In some embodiments, the medical device includes tubing. In some embodiments, the medical device includes wires. In some embodiments, the medical device includes an electrode. In some embodiments, the medical device includes a clip. In some embodiments, the medical device includes a fastener. In some embodiments, the medical device comprises a syringe. In some embodiments, the medical device comprises a container. In some cases, the devices described herein comprise a dental instrument or a medical instrument. In some cases, the devices described herein comprise an implant, an IV, a prosthesis, a suture material, a valve, a stent, a catheter, a rod, a shunt, a scope, a contact lens, tubing, wiring, an electrode, a clip, a fastener, a syringe, a container, or a combination thereof. In some embodiments, the device comprises an implant. In some embodiments, the device comprises an IV. In some embodiments, the device comprises a prosthesis. In some embodiments, the device comprises a suture material. In some embodiments, the device comprises a valve.In some embodiments, the device comprises a stent. In some embodiments, the device comprises a catheter. In some embodiments, the device comprises a rod. In some embodiments, the device comprises a shunt. In some embodiments, the device comprises a scope. In some embodiments, the device comprises a contact lens. In some embodiments, the device comprises tubing. In some embodiments, the device comprises a wire. In some embodiments, the device comprises an electrode. In some embodiments, the device comprises a clip. In some embodiments, the device comprises a fastener. In some embodiments, the device comprises a syringe. In some embodiments, the device comprises a container.

[0206] In some embodiments, the compounds described herein are coated on medical devices. In some cases, the compounds described herein are coated on medical devices to prevent and / or reduce biofouling (e.g., bacterial adhesion or micro-biofouling, such as biofilms). In some cases, the compounds described herein are coated on dental or medical instruments to prevent and / or reduce biofouling (e.g., bacterial adhesion or micro-biofouling, such as biofilms). In some cases, the compounds described herein are coated on implants, IVs, prostheses, suture materials, valves, stents, catheters, rods, shunts, scopes, contact lenses, tubing, wiring, electrodes, clips, fasteners, syringes, containers, or combinations thereof to prevent and / or reduce biofouling (e.g., bacterial adhesion or micro-biofouling, such as biofilms).

[0207] In some cases, the devices described herein include a catheter. In some cases, the catheter includes an indwelling catheter. In some cases, the catheter includes a permcath. In some cases, the catheter includes a ureteral catheter or a Foley catheter.

[0208] In some cases, the compounds described herein are coated onto catheters to prevent and / or reduce biofouling (e.g., bacterial adhesion or micro-biofouling such as biofilms). In some cases, the compounds described herein are coated onto indwelling catheters to prevent and / or reduce biofouling (e.g., bacterial adhesion or micro-biofouling such as biofilms). In some cases, the compounds described herein are coated onto permacus to prevent and / or reduce biofouling (e.g., bacterial adhesion or micro-biofouling such as biofilms). In some cases, the compounds described herein are coated onto ureteral catheters to prevent and / or reduce biofouling (e.g., bacterial adhesion or micro-biofouling such as biofilms). In some cases, the compounds described herein are coated onto Foley catheters to prevent and / or reduce biofouling (e.g., bacterial adhesion or micro-biofouling such as biofilms).

[0209] In some cases, the devices described herein include an implant. In some cases, the implant includes a dental implant or an orthopedic implant. In some cases, the devices described herein include a dental implant. In other cases, the devices described herein include an orthopedic implant.

[0210] In some cases, the compounds described herein are coated onto implants to prevent and / or reduce biofouling (e.g., bacterial adhesion or microbiofouling such as biofilms). In some cases, the compounds described herein are coated onto dental implants to prevent and / or reduce biofouling (e.g., bacterial adhesion or microbiofouling such as biofilms). In some cases, the compounds described herein are coated onto orthopedic implants to prevent and / or reduce biofouling (e.g., bacterial adhesion or microbiofouling such as biofilms).

[0211] In some embodiments, the devices described herein include an IV. In some cases, a compound described herein is coated onto the IV to prevent and / or reduce biofouling (e.g., bacterial adhesion or microbiofouling such as biofilms).

[0212] In some embodiments, the devices described herein include a prosthesis. In some cases, the prosthesis includes an artificial bone, an artificial joint, an artificial organ, or a denture. In some cases, the artificial organ includes an artificial pancreas, an artificial heart, a prosthetic limb, or a heart valve. In some embodiments, the devices described herein include an artificial bone, an artificial joint, an artificial organ, or a denture. In some embodiments, the devices described herein include an artificial pancreas, an artificial heart, a prosthetic limb, or a heart valve.

[0213] In some cases, the compounds described herein are coated onto a prosthesis to prevent and / or reduce biofouling (e.g., bacterial adhesion or micro-biofouling such as biofilms). In some cases, the compounds described herein are coated onto an artificial bone, an artificial joint, an artificial organ, or a denture to prevent and / or reduce biofouling (e.g., bacterial adhesion or micro-biofouling such as biofilms). In some cases, the compounds described herein are coated onto an artificial pancreas, an artificial heart, an artificial limb, or a heart valve to prevent and / or reduce biofouling (e.g., bacterial adhesion or micro-biofouling such as biofilms).

[0214] In some embodiments, the devices described herein include stents. In some cases, stents are small, expandable tubes used to keep open passages in blood vessels or ducts. In some cases, stents include coronary stents, vascular stents, or biliary stents. In some cases, coronary stents are also referred to as cardiac stents or heart stents. In some embodiments, the devices described herein include coronary stents, vascular stents, or biliary stents.

[0215] In some cases, the compounds described herein are coated onto a stent to prevent and / or reduce biofouling (e.g., bacterial adhesion or microbiofouling such as biofilms). In some cases, the compounds described herein are coated onto a coronary stent, a vascular stent, or a biliary stent to prevent and / or reduce biofouling (e.g., bacterial adhesion or microbiofouling such as biofilms).

[0216] In some cases, the devices described herein include a shunt. In some cases, a shunt is a hole or small passageway that allows the movement of fluid from one part of the body to another. In some cases, a shunt differs from a stent in that a shunt connects two previously unconnected parts. In some cases, a shunt is an acquired shunt. In some cases, a shunt includes a cardiac shunt, a cerebral shunt, a lumbar-peritoneal shunt, a peritoneovenous shunt, a pulmonary shunt, a portosystemic shunt (PSS), a portocaval shunt, or a vesico-amniotic shunt. In some cases, a cardiac shunt includes a right-to-left, left-to-right, or bidirectional shunt. In some cases, a cerebral shunt includes the drainage of excess cerebrospinal fluid from the brain into the thoracic or peritoneal cavity. In some cases, a lumbar-peritoneal shunt includes the channeling of cerebrospinal fluid from the lumbar thecal sac into the peritoneal cavity. In some cases, a peritoneovenous shunt (also called a Denver shunt) drains ascites from the peritoneum into the veins. In some cases, the portosystemic shunt (PSS) is a liver shunt that allows bypass of the liver by the circulatory system. In some cases, the portocaval shunt connects the portal vein with the inferior vena cava for the treatment of hypertension in the liver. In some cases, the vesicoamniotic shunt is for draining excess fluid in the fetal bladder to the surrounding area. In some cases, the devices described herein include a cardiac shunt, a cerebral shunt, a lumboperitoneal shunt, a peritoneal venous shunt, a pulmonary shunt, a portosystemic shunt (PSS), a portocaval shunt, or a vesicoamniotic shunt.

[0217] In some cases, a compound described herein is coated onto a shunt to prevent and / or reduce biofouling (e.g., bacterial adhesion or microbiofouling such as biofilms). In some cases, a compound described herein is coated onto a cardiac shunt, a cerebral shunt, a lumbar-peritoneal shunt, a peritoneovenous shunt, a pulmonary shunt, a portosystemic shunt (PSS), a portocaval shunt, or a bladder-amniotic shunt to prevent and / or reduce biofouling (e.g., bacterial adhesion or microbiofouling such as biofilms).

[0218] In some cases, the devices described herein include a scope. In some cases, the scope is a medical instrument used in image-guided surgery. In some cases, the scope includes an endoscope or a laparoscope. Endoscopy is a medical procedure for examining the digestive tract with an endoscope. In some cases, endoscopy further includes sigmoidoscopy and colonoscopy. Laparoscopy is a diagnostic procedure for examining internal organs utilizing a laparoscope. In some cases, the devices described herein include a scope used in endoscopy. In other cases, the devices described herein include a scope used in laparoscopy.

[0219] In some cases, the compounds described herein are coated onto a scope to prevent and / or reduce biofouling (e.g., bacterial adhesion or micro-biofouling such as biofilms). In some cases, the compounds described herein are coated onto an endoscope to prevent and / or reduce biofouling (e.g., bacterial adhesion or micro-biofouling such as biofilms). In some cases, the compounds described herein are coated onto a laparoscope to prevent and / or reduce biofouling (e.g., bacterial adhesion or micro-biofouling such as biofilms).

[0220] In some embodiments, the devices described herein include suture material, valves, rods, tubing, wires, electrodes, clips, fasteners, or combinations thereof. In some cases, the compounds described herein are coated onto suture material, valves, rods, tubing, wires, electrodes, clips, fasteners, or combinations thereof to prevent and / or reduce biofouling (e.g., bacterial adhesion or microbiofouling such as biofilms).

[0221] In some embodiments, the device described herein comprises a syringe. In some cases, the syringe further comprises a needle. In some cases, the compound described herein is coated onto the syringe to prevent and / or reduce biofouling (e.g., bacterial adhesion or microbiofouling such as biofilms).

[0222] In some embodiments, the devices described herein include a container, such as for storing one or more medical devices. In some cases, the compounds described herein are coated onto the container to prevent and / or reduce biofouling (e.g., bacterial adhesion or microbiofouling such as biofilms).

[0223] In some embodiments, the devices described herein comprise a bandage or patch. In some cases, the devices described herein comprise a bandage. In other cases, the devices described herein comprise a patch.

[0224] In some cases, the compounds described herein are coated onto a dressing to prevent and / or reduce biofouling (e.g., bacterial adhesion or microbiofouling such as biofilms). In some cases, the compounds described herein are coated onto a patch to prevent and / or reduce biofouling (e.g., bacterial adhesion or microbiofouling such as biofilms).

[0225] In one aspect, described herein is a device coated with a compound of formula (I): [ka] During the ceremony, A is -C(=O)-, -S(=O)-, -S(=O) 2 - and -S(=O)(-NR 3 )- is selected from L is -OQ, -NR 3 Q, and -N(R 3 ) 2 Q +is selected from Q is a structure represented by the following formula: [ka] Z is -CR 6a R 6b -, -C(=O)-, -C(=NH)-, and -C(=NH)NR 7 - selected from m is an integer selected from 0, 1, 2, 3, 4, 5, 6, 7, and 8; Each R 1a and R 1b is independently selected from hydrogen and halogen; Each R 2a and R 2b are independently selected from halogen, -CN, and optionally substituted C 1 -C 6 fluoroalkyl; Each R 3 are independently hydrogen, optionally substituted C 1 -C 4 Alkyl, -X-optionally substituted C 1 -C 4 selected from alkyl, optionally substituted aryl, and -X-optionally substituted aryl; X is -C(=O)-, -S(=O)-, or -S(=O) 2 - and Each R 4a , R 4b , R 5a , R 5c , R 6a , and R 6b are independently hydrogen, halogen, -CN, -OR 9 , optionally substituted C 1 -C 4 Alkyl, optionally substituted C 1 -C 4 Fluoroalkyl, optionally substituted aryl, -NR 8a R 8b , -NR 8a R 8b R 8c+ , -S(=O)2 O - , -S(=O) 2 OR 9 , -C(=O)O - , and -C(=O)OR 9 is selected from R 5b -OR 10b , -NR 10a R 10b , or -NR 10a R 10b R 10c+ and Each R 7 , R 8a , R 8b , R 8c , and R 9 are independently hydrogen and optionally substituted C 1 -C 4 selected from alkyl and optionally substituted aryl; Each R 10a and R 10c are independently hydrogen, optionally substituted C 1 -C 4 Alkyl, optionally substituted aryl, -(optionally substituted C 1 -C 8 Alkylene)S(=O) 2 O - , -(optionally substituted C 1 -C 8 Alkylene)S(=O) 2 OH, -(optionally substituted C 1 -C 8 Alkylene)C(=O)O - , and -(optionally substituted C 1 -C 8 alkylene)C(=O)OH; R 10b is -C(=O)-C 2 -C 6 Alkenyl, -S(=O)-C 2 -C 6 Alkenyl, or -S(=O) 2 -C 2 -C 6 It is alkenyl.

[0226] In some embodiments, the compound of formula (I) is N-(2-((4-azido-2,3,5,6-tetrafluorophenyl)sulfonamido)ethyl)methacrylamide, N-(2-acrylamidoethyl)-4-azido-2,3,5,6-tetrafluorobenzamide, or Not 2-(methacryloyloxy)ethyl 4-azido-2,3,5,6-tetrafluorobenzoate.

[0227] In some embodiments, the device coated with the compound of formula (I) comprises a residue of the compound of formula (I). In some embodiments, the residue of the compound of formula (I) comprises a singlet nitrene residue.

[0228] In some embodiments, the compound of formula (I) has the structure above.

[0229] In some embodiments, the different variables of the compound of formula (I) are as described above.

[0230] In some embodiments, the compound of formula (I) has the structure of formula (Ia), (Ib), (Ic), (Id), (Ie), (If), (Ig), or (Ih) above.

[0231] In some embodiments, the compound of formula (I) is selected from the compounds described above.

[0232] In another aspect, described herein is a device coated with a compound of formula (II): [ka] During the ceremony, Each R 1a and R 1b is independently selected from hydrogen and halogen; Each R 2a and R 2bare independently selected from halogen, -CN, and optionally substituted C 1 -C 6 fluoroalkyl; Each A 1 , A 2 , and A 3 are independently -C(=O)-, -S(=O)-, -S(=O) 2 - and -S(=O)(=NR 3c )- is selected from Each B 1 , B 2 , and B. 3 are independently -O- and -NR 3c - selected from D is -S(=O) 2 O - , -S(=O) 2 OR 9a , -C(=O)O - , or -C(=O)OR 9a and Z 1 is -(CR 6c R 6d ) s - and Z 2 is -(CR 6c R 6d ) t - and Z 3 is -(CR 6c R 6d ) p - and Each R 3a and R 3b are independently hydrogen, optionally substituted C 1 -C 4 alkyl, and optionally substituted benzyl; Each R 4c , R 4d , R 5d , R 5e , R 6c , and R 6d are independently hydrogen, halogen, -CN, -OR 9a , optionally substituted C 1 -C 4Alkyl, optionally substituted C 1 -C 4 Fluoroalkyl, optionally substituted C 2 -C 6 Alkenyl, -NR 3c R 3d , -S(=O) 2 O - , -S(=O) 2 OR 9a , -C(=O)O - , and -C(=O)OR 9a is selected from Each R 3c and R 3d are independently hydrogen, optionally substituted C 1 -C 4 Alkyl, -X-optionally substituted C 1 -C 4 Alkyl, optionally substituted C 2 -C 6 alkenyl, and optionally substituted aryl; X is -C(=O)-, -S(=O)-, or -S(=O) 2 - and Each R 9a , R 11a , R 11b , R 11c , R 12a , R 12b , and R 12c are independently hydrogen, optionally substituted C 1 -C 4 alkyl, and optionally substituted aryl; n is an integer selected from 0, 1, 2, 3, 4, 5, 6, 7, and 8; s is an integer selected from 1, 2, 3, 4, or 5; t is an integer selected from 1, 2, 3, 4, or 5; p is an integer selected from 1, 2, 3, 4, or 5; 0 <x<1であり、 The compounds of formula (II) are charged or zwitterionic.

[0233] In some embodiments, the compound of formula (II) is [ka] isn't it.

[0234] In some embodiments, x in formula (II) is not about 0.9434.

[0235] In some embodiments, the compound of formula (II) is not obtained by using 2 g of sulfobetaine methacrylate monomer and 156 mg of perfluorophenyl azide methacrylamide monomer.

[0236] In some embodiments, the different variables of the compound of formula (II) are as described above.

[0237] In another aspect, described herein is a device coated with a compound of formula (III): [ka] During the ceremony, Each R 1a and R 1b is independently selected from hydrogen and halogen; Each R 2a and R 2b are independently selected from halogen, -CN, and optionally substituted C 1 -C 6 fluoroalkyl; Each A 1 , A 2 , and A 3 are independently -C(=O)-, -S(=O)-, -S(=O) 2 - and -S(=O)(=NR 3c )- is selected from Each B 1 , B 2 , and B. 3 are independently -O- and -NR 3c - selected from Z 1 is -(CR6c R 6d ) s - and Z 2 is -(CR 6c R 6d ) t - and E is -CN, -OR 9a , -NR 9a R 9b , -NR 9a R 9b R 9c+ , optionally substituted C 1 -C 4 Alkyl, optionally substituted C 1 -C 6 Fluoroalkyl, -S(=O) 2 O - , -S(=O) 2 OR 9a , -C(=O)O - , or -C(=O)OR 9a and Each R 4c , R 4d , R 5d , R 5e , R 6c , and R 6d are independently hydrogen, halogen, -CN, -OR 9a , optionally substituted C 1 -C 4 Alkyl, optionally substituted C 1 -C 4 Fluoroalkyl, optionally substituted C 2 -C 6 Alkenyl, -NR 3c R 3d , -S(=O) 2 O - , -S(=O) 2 OR 9a , -C(=O)O - , and -C(=O)OR 9a is selected from Each R 3c and R 3d are independently hydrogen, optionally substituted C 1 -C 4 Alkyl, -X-optionally substituted C1 -C 4 Alkyl, optionally substituted C 2 -C 6 alkenyl, and optionally substituted aryl; X is -C(=O)-, -S(=O)-, or -S(=O) 2 - and Each R 9a , R 9b , R 9c , R 11a , R 11b , R 11c , R 12a , R 12b , and R 12c are independently hydrogen, optionally substituted C 1 -C 4 alkyl, and optionally substituted aryl; n is an integer selected from 0, 1, 2, 3, 4, 5, 6, 7, and 8; s is an integer selected from 1, 2, 3, 4, or 5; t is an integer selected from 1, 2, 3, 4, or 5; 0 <x<1である。

[0238] In some embodiments, the compound of formula (III) is charged or zwitterionic. In some embodiments, the compound of formula (III) comprises a positively charged repeat unit. In some embodiments, the compound of formula (III) comprises a negatively charged repeat unit. In some embodiments, the compound of formula (III) comprises a positively charged repeat unit and a negatively charged repeat unit. In some embodiments, the ratio of the positively charged repeat unit to the negatively charged repeat unit in the compound of formula (III) is about 10:1 to about 1:10. In some embodiments, the ratio of the positively charged repeat unit to the negatively charged repeat unit in the compound of formula (III) is about 5:1 to about 1:5. In some embodiments, the ratio of the positively charged repeat unit to the negatively charged repeat unit in the compound of formula (III) is about 2:1 to about 1:2. In some embodiments, the ratio of the positively charged repeat unit to the negatively charged repeat unit in the compound of formula (III) is about 1:1.

[0239] In some embodiments, the different variables of the compound of formula (III) are as described above.

[0240] In another aspect, described herein is a device coated with a copolymer, the copolymer comprising: a) a repeating unit of formula (VII): [ka] (In the formula, Each R 1a and R 1b is independently selected from hydrogen and halogen; Each R 2a and R 2b are independently selected from halogen, -CN, and optionally substituted C 1 -C 6 fluoroalkyl; Each A 1 and A 2 are independently -C(=O)-, -S(=O)-, -S(=O) 2 - and -S(=O)(=NR 3c )- is selected from Each B 1 and B. 2 are independently -O- and -NR 3c - selected from Z 1 is -(CR 6c R 6d ) s - and Each R 4c , R 4d , R 5d , R 5e , R 6c , and R 6d are independently hydrogen, halogen, -CN, -OR 9a , optionally substituted C 1 -C 4 Alkyl, optionally substituted C 1 -C 4 Fluoroalkyl, optionally substituted C 2 -C6 Alkenyl, -NR 3c R 3d , -S(=O) 2 O - , -S(=O) 2 OR 9a , -C(=O)O - , and -C(=O)OR 9a is selected from Each R 3c and R 3d are independently hydrogen, optionally substituted C 1 -C 4 Alkyl, -X-optionally substituted C 1 -C 4 Alkyl, optionally substituted C 2 -C 6 alkenyl, and optionally substituted aryl; X is -C(=O)-, -S(=O)-, or -S(=O) 2 - and Each R 9a , R 11a , R 11b , and R 11c are independently hydrogen, optionally substituted C 1 -C 4 alkyl, and optionally substituted aryl; n is an integer selected from 0, 1, 2, 3, 4, 5, 6, 7, and 8; s is an integer selected from 1, 2, 3, 4, and 5; b) A repeating unit of formula (VIII): [ka] (In the formula, A 3 -C(=O)-, -S(=O)-, -S(=O) 2 - or -S(=O)(=NR 3c )-and B 3 is -O- or -NR 3c - and D is -S(=O) 2 O -, -S(=O) 2 OR 9a , -C(=O)O - , or -C(=O)OR 9a and Z 2 is -(CR 6c R 6d ) t - and Z 3 is -(CR 6c R 6d ) p - and Each R 3a and R 3b are independently hydrogen, optionally substituted C 1 -C 4 alkyl, and optionally substituted benzyl; Each R 6c and R 6d are independently hydrogen, halogen, -CN, -OR 9a , optionally substituted C 1 -C 4 Alkyl, optionally substituted C 1 -C 4 Fluoroalkyl, optionally substituted C 2 -C 6 Alkenyl, -NR 3c R 3d , -S(=O) 2 O - , -S(=O) 2 OR 9a , -C(=O)O - , and -C(=O)OR 9a is selected from Each R 3c and R 3d are independently hydrogen, optionally substituted C 1 -C 4 Alkyl, -X-optionally substituted C 1 -C 4 Alkyl, optionally substituted C 2 -C 6 alkenyl, and optionally substituted aryl; X is -C(=O)-, -S(=O)-, or -S(=O)2 - and Each R 9a , R 12a , R 12b , and R 12c are independently hydrogen, optionally substituted C 1 -C 4 alkyl, and optionally substituted aryl; t is an integer selected from 1, 2, 3, 4, or 5; p is an integer selected from 1, 2, 3, 4, or 5; A repeat unit of formula (VIII), wherein the repeat unit of formula (VIII) is charged or zwitterionic; c) A repeating unit of formula (IX): [ka] (A 4 -C(=O)-, -S(=O)-, -S(=O) 2 - or -S(=O)(=NR 3c )-and B 4 is -O- or -NR 3c - and Z 4 is -(CR 6c R 6d ) k - and E is -CN, -OR 9a , -NR 9a R 9b , -NR 9a R 9b R 9c+ , optionally substituted C 1 -C 4 Alkyl, optionally substituted C 1 -C 6 Fluoroalkyl, -S(=O) 2 O - , -S(=O) 2 OR 9a , -C(=O)O - , or -C(=O)OR 9a and Each R 6c and R6d are independently hydrogen, halogen, -CN, -OR 9a , optionally substituted C 1 -C 4 Alkyl, optionally substituted C 1 -C 4 Fluoroalkyl, optionally substituted C 2 -C 6 Alkenyl, -NR 3c R 3d , -S(=O) 2 O - , -S(=O) 2 OR 9a , -C(=O)O - , and -C(=O)OR 9a is selected from Each R 3c and R 3d are independently hydrogen, optionally substituted C 1 -C 4 Alkyl, -X-optionally substituted C 1 -C 4 Alkyl, optionally substituted C 2 -C 6 alkenyl, and optionally substituted aryl; X is -C(=O)-, -S(=O)-, or -S(=O) 2 - and Each R 9a , R 9b , R 9c , R 13a , R 13b , and R 13c are independently hydrogen, optionally substituted C 1 -C 4 alkyl, and optionally substituted aryl; and k is an integer selected from 1 to 10.

[0241] In some embodiments, the recurring unit of formula (IX) is charged or zwitterionic.

[0242] In some embodiments, the different variables of the compounds of formula (VII), formula (VIII), and formula (IX) are as described above.

[0243] Biofouling Resistant Devices In some embodiments, biofouling resistant medical devices are disclosed herein, where the surface of the medical device is coated with one or more compounds of formula (I), (II), or (III) described herein having a number average molecular weight of about 10,000 to about 250,000. In some embodiments, biofouling resistant medical devices are disclosed herein, where the surface of the medical device is coated with one or more copolymers comprising repeat units of formula (VII), (VIII), and (IX) described herein having a number average molecular weight of about 10,000 to about 250,000.

[0244] In some embodiments, the phenyl azide-based copolymers have a number average molecular weight of at least about 10,000, about 20,000, about 30,000, about 40,000, about 50,000, about 60,000, about 70,000, about 80,000, about 90,000, about 100,000, about 110,000, about 120,000, about 130,000, about 140,000, about 150,000, about 160,000, about 170,000, about 180,000, about 190,000, or about 200,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of less than or equal to about 10,000, about 20,000, about 30,000, about 40,000, about 50,000, about 60,000, about 70,000, about 80,000, about 90,000, about 100,000, about 110,000, about 120,000, about 130,000, about 140,000, about 150,000, about 160,000, about 170,000, about 180,000, about 190,000, or about 200,000.

[0245] In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 10,000 to about 20,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 10,000 to about 40,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 10,000 to about 60,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 10,000 to about 80,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 10,000 to about 100,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 10,000 to about 120,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 10,000 to about 140,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 10,000 to about 160,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 10,000 to about 200,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 20,000 to about 40,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 20,000 to about 60,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 20,000 to about 80,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 20,000 to about 100,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 20,000 to about 120,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 20,000 to about 140,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 20,000 to about 160,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 20,000 to about 200,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 20,000 to about 250,000.In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 40,000 to about 60,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 40,000 to about 80,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 40,000 to about 100,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 40,000 to about 120,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 40,000 to about 140,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 40,000 to about 160,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 40,000 to about 200,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 40,000 to about 250,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 60,000 to about 80,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 60,000 to about 100,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 60,000 to about 120,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 60,000 to about 140,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 60,000 to about 160,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 60,000 to about 200,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 60,000 to about 250,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 80,000 to about 100,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 80,000 to about 120,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 80,000 to about 140,000.In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 80,000 to about 160,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 80,000 to about 200,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 80,000 to about 250,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 100,000 to about 120,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 100,000 to about 140,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 100,000 to about 160,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 100,000 to about 200,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 100,000 to about 250,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 120,000 to about 140,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 120,000 to about 160,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 120,000 to about 200,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 120,000 to about 250,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 140,000 to about 160,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 140,000 to about 200,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 140,000 to about 250,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 160,000 to about 200,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 160,000 to about 250,000.In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 200,000 to about 250,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 10,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 20,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 40,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 60,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 80,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 100,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 120,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 140,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 160,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 200,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 250,000.

[0246] In some embodiments, biofouling resistant medical devices are disclosed herein, where the surface of the medical device is coated with one or more compounds of formula (I), (II), or (III) described herein having a number average molecular weight of about 14,000 to about 21,000. In some embodiments, biofouling resistant medical devices are disclosed herein, where the surface of the medical device is coated with one or more copolymers comprising repeat units of formula (VII), (VIII), and (IX) described herein having a number average molecular weight of about 14,000 to about 21,000.

[0247] In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 14,000 to about 15,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 14,000 to about 16,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 14,000 to about 17,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 14,000 to about 18,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 14,000 to about 19,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 14,000 to about 20,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 15,000 to about 16,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 15,000 to about 17,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 15,000 to about 18,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 15,000 to about 19,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 15,000 to about 20,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 15,000 to about 21,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 16,000 to about 17,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 16,000 to about 18,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 16,000 to about 19,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 16,000 to about 20,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 16,000 to about 21,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 17,000 to about 18,000.In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 17,000 to about 19,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 17,000 to about 20,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 17,000 to about 21,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 18,000 to about 19,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 18,000 to about 20,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 18,000 to about 20,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 18,000 to about 21,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 19,000 to about 20,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 19,000 to about 21,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 20,000 to about 21,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 14,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 15,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 16,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 17,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 18,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 19,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 20,000. In some embodiments, the phenyl azide-based copolymer has a number average molecular weight of about 21,000.

[0248] In some embodiments, biofouling resistant medical devices are disclosed herein, where the surface of the medical device is coated with one or more compounds of formula (I), (II), or (III) described herein having a polydispersity index (PDI) of about 1 to about 1.5. In some embodiments, biofouling resistant medical devices are disclosed herein, where the surface of the medical device is coated with one or more copolymers comprising repeat units of formula (VII), (VIII), and (IX) described herein having a polydispersity index (PDI) of about 1 to about 1.5.

[0249] In some embodiments, the surface of a medical device is coated with a phenylazide-based copolymer having a polydispersity index (PDI) of at least about 1, about 1.1, about 1.2, about 1.3, about 1.4, or about 1.5. In some embodiments, the surface of a medical device is coated with a phenylazide-based copolymer having a polydispersity index (PDI) of at least about 1, about 1.1, about 1.2, about 1.3, about 1.4, or about 1.5 or less.

[0250] In some embodiments, the surface of the medical device is coated with a phenyl azide-based copolymer having a polydispersity index (PDI) of about 1-1.1. In some embodiments, the surface of the medical device is coated with a phenyl azide-based copolymer having a polydispersity index (PDI) of about 1-1.2. In some embodiments, the surface of the medical device is coated with a phenyl azide-based copolymer having a polydispersity index (PDI) of about 1-1.3. In some embodiments, the surface of the medical device is coated with a phenyl azide-based copolymer having a polydispersity index (PDI) of about 1-1.4. In some embodiments, the surface of the medical device is coated with a phenyl azide-based copolymer having a polydispersity index (PDI) of about 1-1.5. In some embodiments, the surface of the medical device is coated with a phenyl azide-based copolymer having a polydispersity index (PDI) of about 1.1-1.2. In some embodiments, the surface of the medical device is coated with a phenyl azide-based copolymer having a polydispersity index (PDI) of about 1.1-1.3. In some embodiments, the surface of the medical device is coated with a phenyl azide-based copolymer having a polydispersity index (PDI) of about 1.1-1.4. In some embodiments, the surface of the medical device is coated with a phenyl azide-based copolymer having a polydispersity index (PDI) of about 1.1-1.5. In some embodiments, the surface of the medical device is coated with a phenyl azide-based copolymer having a polydispersity index (PDI) of about 1.2-1.3. In some embodiments, the surface of the medical device is coated with a phenyl azide-based copolymer having a polydispersity index (PDI) of about 1.2-1.4. In some embodiments, the surface of the medical device is coated with a phenyl azide-based copolymer having a polydispersity index (PDI) of about 1.2-1.5. In some embodiments, the surface of the medical device is coated with a phenyl azide-based copolymer having a polydispersity index (PDI) of about 1.3-1.4. In some embodiments, the surface of the medical device is coated with a phenyl azide-based copolymer having a polydispersity index (PDI) of about 1.3 to 1.5.In some embodiments, the surface of the medical device is coated with a phenyl azide-based copolymer having a polydispersity index (PDI) of about 1.4 to 1.5. In some embodiments, the PDI is about 1. In some embodiments, the PDI is about 1.1. In some embodiments, the PDI is about 1.2. In some embodiments, the PDI is about 1.3. In some embodiments, the PDI is about 1.4. In some embodiments, the PDI is about 1.5. In some embodiments, the PDI is about 1.11. In some embodiments, the PDI is about 1.12. In some embodiments, the PDI is about 1.13. In some embodiments, the PDI is about 1.14. In some embodiments, the PDI is about 1.15. In some embodiments, the PDI is about 1.16. In some embodiments, the PDI is about 1.17. In some embodiments, the PDI is about 1.18. In some embodiments, the PDI is about 1.19. In some embodiments, the PDI is about 1.21. In some embodiments, the PDI is about 1.22. In some embodiments, the PDI is about 1.23. In some embodiments, the PDI is about 1.24. In some embodiments, the PDI is about 1.25.

[0251] In some embodiments, the medical device comprises a dental instrument or a medical instrument. In some embodiments, the medical device comprises an implant, an IV, a prosthesis, a suture material, a valve, a stent, a catheter, a rod, a shunt, a scope, a contact lens, tubing, a wire, an electrode, a clip, a fastener, a syringe, a container, or a combination thereof. In some embodiments, the medical device is a contact lens. In some embodiments, the medical device is a catheter. In some embodiments, the catheter is an indwelling catheter. In some embodiments, the catheter comprises a ureteral catheter or a Foley catheter. In some embodiments, the medical device is a scope. In some embodiments, the scope comprises a scope utilized in image-guided surgery. In some embodiments, the scope comprises a scope utilized in endoscopy or laparoscopy.

[0252] In some embodiments, the medical device comprises a hearing aid, an artificial larynx, a dental implant, a breast implant, a penile implant, a cranial / facial tendon, a tendon, a ligament, a meniscus, or an intervertebral disc. In some embodiments, the medical device comprises an artificial bone, an artificial joint, or an artificial organ. In some embodiments, the artificial organ comprises an artificial pancreas, an artificial heart, an artificial limb, or a heart valve. In some embodiments, the medical device comprises a bandage or patch.

[0253] In some embodiments, the copolymer comprises a zwitterionic copolymer. In some embodiments, the zwitterionic copolymer comprises polysulfobetaine.

[0254] In some embodiments, the biofouling is caused by bacteria, viruses, and / or fungi.

[0255] Non-medical devices In some embodiments, the device described herein comprises a non-medical device. In some cases, the non-medical device comprises a vessel or underwater structure. In some cases, the surface of the non-medical device for coating with the compound described herein comprises a surface that is immersed in water. In some cases, the immersion is at least 30 minutes, 1 hour, 6 hours, 12 hours, 1 day, 2 days, 3 days, 4 days, 5 days, 6 days, 7 days, 8 days, 9 days, 10 days, 11 days, 12 days, 13 days, 14 days, 15 days, 30 days, 1 month, 2 months, 3 months, 4 months, 5 months, 6 months, 7 months, 8 months, 9 months, 10 months, 11 months, 1 year, 2 years, 3 years, 4 years, 5 years, 10 years, or more.

[0256] In some cases, the device described herein comprises a vessel. In some cases, the surface of the vessel comprises a surface that is submerged in water. In some cases, the surface of the vessel comprises a surface that is submerged in water for at least 30 minutes, 1 hour, 6 hours, 12 hours, 1 day, 2 days, 3 days, 4 days, 5 days, 6 days, 7 days, 8 days, 9 days, 10 days, 11 days, 12 days, 13 days, 14 days, 15 days, 30 days, 1 month, 2 months, 3 months, 4 months, 5 months, 6 months, 7 months, 8 months, 9 months, 10 months, 11 months, 1 year, 2 years, 3 years, 4 years, 5 years, 10 years, or more. In some cases, the surface of the device for coating with the compound described herein comprises the hull of a vessel.

[0257] In some cases, the devices described herein include an underwater structure. In some cases, the underwater structure includes an underwater cable, a current measurement device, or an offshore oil platform. In some cases, the devices described herein include an underwater cable. In some cases, the devices described herein include a current measurement device. In other cases, the devices described herein include an offshore oil platform.

[0258] In some cases, a submersible structure is one where the structure is submerged in water for at least 30 minutes, 1 hour, 6 hours, 12 hours, 1 day, 2 days, 3 days, 4 days, 5 days, 6 days, 7 days, 8 days, 9 days, 10 days, 11 days, 12 days, 13 days, 14 days, 15 days, 30 days, 1 month, 2 months, 3 months, 4 months, 5 months, 6 months, 7 months, 8 months, 9 months, 10 months, 11 months, 1 year, 2 years, 3 years, 4 years, 5 years, or more. In some cases, the surface of the submersible structure is a structure where the surface is submerged in water for at least 30 minutes, 1 hour, 6 hours, 12 hours, 1 day, 2 days, 3 days, 4 days, 5 days, 6 days, 7 days, 8 days, 9 days, 10 days, 11 days, 12 days, 13 days, 14 days, 15 days, 30 days, 1 month, 2 months, 3 months, 4 months, 5 months, 6 months, 7 months, 8 months, 9 months, 10 months, 11 months, 1 year, 2 years, 3 years, 4 years, 5 years, 10 years, or more. In some cases, the devices described herein include submersible structures where the surface is submerged in water for at least 30 minutes, 1 hour, 6 hours, 12 hours, 1 day, 2 days, 3 days, 4 days, 5 days, 6 days, 7 days, 8 days, 9 days, 10 days, 11 days, 12 days, 13 days, 14 days, 15 days, 30 days, 1 month, 2 months, 3 months, 4 months, 5 months, 6 months, 7 months, 8 months, 9 months, 10 months, 11 months, 1 year, 2 years, 3 years, 4 years, 5 years, 10 years, or more.

[0259] In some embodiments, the compounds described herein are coated onto a device (e.g., a medical device or a non-medical device). In some cases, the compounds described herein are directly coated onto a device (e.g., a medical device or a non-medical device). In other cases, the compounds described herein are indirectly coated onto a device (e.g., a medical device or a non-medical device). In some cases, the coating comprises dip coating. In other cases, the coating comprises spray coating.

[0260] In some embodiments, the compounds described herein are coated onto a device (e.g., a medical device or a non-medical device) to reduce the formation of biofouling. In some cases, the formation of biofouling is reduced by about 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80%, 90%, 95%, 99%, 99.5%, 99.9% or more compared to a device not coated with the compound. In some cases, the formation of biofouling is reduced by about 10% or more compared to a device not coated with the compound. In some cases, the formation of biofouling is reduced by about 20% or more compared to a device not coated with the compound. In some cases, the formation of biofouling is reduced by about 30% or more compared to a device not coated with the compound. In some cases, the formation of biofouling is reduced by about 40% or more compared to a device not coated with the compound. In some cases, the formation of biofouling is reduced by about 50% or more compared to a device not coated with the compound. In some cases, the formation of biofouling is reduced by about 60% or more compared to a device not coated with the compound. In some cases, the formation of biofouling is reduced by about 70% or more compared to a device not coated with the compound. In some cases, the formation of biofouling is reduced by about 80% or more compared to a device not coated with the compound. In some cases, the formation of biofouling is reduced by about 90% or more compared to a device not coated with the compound. In some cases, the formation of biofouling is reduced by about 95% or more compared to a device not coated with the compound. In some cases, the formation of biofouling is reduced by about 99% or more compared to a device not coated with the compound. In some cases, the formation of biofouling is reduced by about 99.5% or more compared to a device not coated with the compound.In some cases, biofouling formation is reduced by about 99.9% or more compared to a device that is not coated with the compound.

[0261] IV. Preparation method In a further aspect, described herein is a method of preparing a biofouling resistant device, the method comprising: a) contacting a surface of the device with a mixture (e.g., a solution) comprising a copolymer; b) treating the surface of the device of step a) with a light source for a time sufficient to effect photo-grafting of the copolymer onto the surface of the device, thereby producing a biofouling resistant device; The copolymers include phenyl azide-based copolymers, the copolymers having a number average molecular weight of about 10,000 to about 250,000.

[0262] In some embodiments, a method of preparing a copolymer-modified biofouling resistant silicon-based device is also described herein, the method comprising: a) contacting a surface of a silicon-based device with a mixture (e.g., a solution) comprising a charged or zwitterionic copolymer; b) treating the surface of the device of step a) with a light source for a time sufficient to effect photo-grafting of the copolymer onto the surface of the silicon-based device, thereby producing a charged or zwitterionic modified device; Charged or zwitterionic copolymers include phenylazide-based copolymers.

[0263] Also described herein in some embodiments is a method of preparing a charged or zwitterionic copolymer-modified biofouling resistant device, the method comprising: a) contacting a surface of the device with a mixture (e.g., a solution) comprising a charged or zwitterionic copolymer; b) treating the surface of the device of step a) with a light source for a time sufficient to effect photo-grafting of the copolymer onto the surface of the device, thereby producing a charged or zwitterionic modified device; The charged or zwitterionic copolymers include phenyl azide-based copolymers, the charged or zwitterionic copolymers having a number average molecular weight of about 10,000 to about 250,000.

[0264] In some embodiments, the method comprises a one-step grafting reaction that modifies the surface of the device.

[0265] In some embodiments, the device is a medical device as described herein. In some embodiments, the device is a non-medical device as described herein.

[0266] In some embodiments, the time sufficient to perform photografting is at least 1 minute, at least 2 minutes, 3 minutes, 4 minutes, 5 minutes, 6 minutes, 7 minutes, 8 minutes, 9 minutes, 10 minutes, 15 minutes, 20 minutes, 25 minutes, or 30 minutes.

[0267] In some embodiments, the light source is an ultraviolet light source. In some embodiments, the ultraviolet light source has a radiation intensity of at least 500 μW / cm 2 In some embodiments, the ultraviolet light source has an intensity of at least 600 μW / cm 2 In some embodiments, the ultraviolet light source has an intensity of at least 700 μW / cm 2 In some embodiments, the ultraviolet light source has an intensity of at least 800 μW / cm 2 In some embodiments, the ultraviolet light source has an intensity of at least 900 μW / cm 2 In some embodiments, the ultraviolet light source has an intensity of at least 1000 μW / cm 2 It has a strength of.

[0268] In some embodiments, the ultraviolet light source has a wavelength of 240 nm to 280 nm, 240 nm to 275 nm, 240 nm to 270 nm, 240 nm to 265 nm, 240 nm to 260 nm, 240 nm to 255 nm, 240 nm to 250 nm, 240 nm to 245 nm, 250 nm to 280 nm, 250 nm to 275 nm, 250 nm to 270 nm, 250 nm to 265 nm, 250 nm to 260 nm, 255 nm to 280 nm, 255 nm to 275 nm, 255 nm to 270 nm, 255 nm to 265 nm, 255 nm to 260 nm, 260 nm to 280 nm, 260 nm to 275 nm, 260 nm to 270 nm, or 270 nm to 280 nm.

[0269] In some embodiments, the ultraviolet light source has a wavelength of at least 240 nm, 245 nm, 250 nm, 251 nm, 252 nm, 253 nm, 254 nm, 255 nm, 256 nm, 257 nm, 258 nm, 259 nm, 260 nm, 261 nm, 262 nm, 263 nm, 264 nm, 265 nm, 266 nm, 267 nm, 268 nm, 269 nm, 270 nm, 275 nm, or 280 nm. In some embodiments, the ultraviolet light source has a wavelength of less than or equal to 240 nm, 245 nm, 250 nm, 251 nm, 252 nm, 253 nm, 254 nm, 255 nm, 256 nm, 257 nm, 258 nm, 259 nm, 260 nm, 261 nm, 262 nm, 263 nm, 264 nm, 265 nm, 266 nm, 267 nm, 268 nm, 269 nm, 270 nm, 275 nm, or 280 nm.

[0270] In a further aspect, described herein is a method of preparing a biofouling resistant device, the method comprising: a) contacting a surface of the device with a mixture (e.g., a solution) comprising a copolymer; b) treating the surface of the device of step a) with a heat source for a time sufficient to effect thermal grafting of the copolymer onto the surface of the device, thereby producing a biofouling resistant device; The copolymers include phenyl azide-based copolymers, the copolymers having a number average molecular weight of about 10,000 to about 250,000.

[0271] In some embodiments, a method of preparing a copolymer-modified biofouling resistant silicon-based device is also described herein, the method comprising: a) contacting a surface of a silicon-based device with a mixture (e.g., a solution) comprising a charged or zwitterionic copolymer; b) treating the surface of the device of step a) with a heat source for a time sufficient to effect thermal grafting of the copolymer onto the surface of the silicon-based device, thereby producing a charged or zwitterionic modified device; Charged or zwitterionic copolymers include phenylazide-based copolymers.

[0272] Also described herein in some embodiments is a method of preparing a charged or zwitterionic copolymer-modified biofouling resistant device, the method comprising: a) contacting a surface of the device with a mixture (e.g., a solution) comprising a charged or zwitterionic copolymer; b) treating the surface of the device of step a) with a heat source for a time sufficient to effect thermal grafting of the copolymer onto the surface of the device, thereby producing a charged or zwitterionic modified device; The charged or zwitterionic copolymers include phenyl azide-based copolymers, the charged or zwitterionic copolymers having a number average molecular weight of about 10,000 to about 250,000.

[0273] In some embodiments, the method comprises a one-step grafting reaction that modifies the surface of the device.

[0274] In some embodiments, the device is a medical device as described herein. In some embodiments, the device is a non-medical device as described herein.

[0275] In some embodiments, the time sufficient to perform thermal grafting is 1 minute, 2 minutes, 3 minutes, 4 minutes, 5 minutes, 6 minutes, 7 minutes, 8 minutes, 9 minutes, 10 minutes, 15 minutes, 20 minutes, 25 minutes, 30 minutes, 45 minutes, 1 hour, 1.5 hours, 2 hours, 3 hours, 4 hours, 5 hours, 6 hours, 9 hours, 12 hours, 18 hours, or 24 hours. In some embodiments, the time sufficient to perform thermal grafting is at least 1 minute, at least 2 minutes, at least 3 minutes, at least 4 minutes, at least 5 minutes, at least 6 minutes, at least 7 minutes, at least 8 minutes, at least 9 minutes, at least 10 minutes, at least 15 minutes, at least 20 minutes, at least 25 minutes, at least 30 minutes, at least 45 minutes, at least 1 hour, at least 1.5 hours, at least 2 hours, at least 3 hours, at least 4 hours, at least 5 hours, at least 6 hours, at least 9 hours, at least 12 hours, or at least 18 hours. In some embodiments, the time sufficient to perform thermal grafting is up to 2 minutes, up to 3 minutes, up to 4 minutes, up to 5 minutes, up to 6 minutes, up to 7 minutes, up to 8 minutes, up to 9 minutes, up to 10 minutes, up to 15 minutes, up to 20 minutes, up to 25 minutes, up to 30 minutes, up to 45 minutes, up to 1 hour, up to 1.5 hours, up to 2 hours, up to 3 hours, up to 4 hours, up to 5 hours, up to 6 hours, up to 9 hours, up to 12 hours, up to 18 hours, or up to 24 hours.

[0276] In some embodiments, the heat source provides a grafting temperature between 40 and 380 degrees Celsius (°C). In some embodiments, the heat source provides a grafting temperature between 40°C and 360°C. In some embodiments, the heat source provides a grafting temperature between 60°C and 320°C. In some embodiments, the heat source provides a grafting temperature between 80°C and 260°C. In some embodiments, the heat source provides a grafting temperature between 100°C and 220°C. In some embodiments, the heat source provides a grafting temperature between 120°C and 220°C. In some embodiments, the heat source provides a grafting temperature of 40°C to 60°C, 60°C to 80°C, 80°C to 100°C, 100°C to 120°C, 120°C to 140°C, 140°C to 160°C, 160°C to 180°C, 180°C to 200°C, 200°C to 220°C, 220°C to 240°C, 240°C to 260°C, 260°C to 280°C, 280°C to 300°C, 300°C to 320°C, 320°C to 340°C, or 340°C to 360°C. In some embodiments, the heat source provides a grafting temperature of 60° C. to 80° C., 80° C. to 100° C., 100° C. to 120° C., 120° C. to 140° C., 140° C. to 160° C., 160° C. to 180° C., 180° C. to 200° C., 200° C. to 220° C., or 220° C. to 240° C. In some embodiments, the heat source provides a grafting temperature of 60° C., 80° C., 100° C., 120° C., 140° C., 160° C., 180° C., 200° C., 220° C., 240° C., 260° C., 280° C., or 300° C. In some embodiments, the heat source provides a grafting temperature of 60° C., 80° C., 100° C., 120° C., 140° C., 160° C., 180° C., 200° C., or 220° C. In some embodiments, the heat source provides a grafting temperature of at least 60° C., at least 80° C., at least 100° C., at least 120° C., at least 140° C., at least 160° C., at least 180° C., at least 200° C., at least 220° C., at least 240° C., at least 260° C., or at least 280° C. In some embodiments, the heat source provides a grafting temperature of up to 80° C., up to 100° C., up to 120° C., up to 140° C., up to 160° C., up to 180° C., up to 200° C., up to 220° C., up to 240° C., up to 260° C., up to 280° C., or up to 300° C.

[0277] In some embodiments, the mixture of step a) is an aqueous solution, an aqueous colloid, or an aqueous suspension. In some embodiments, the mixture of step a) is a non-aqueous solution, an aqueous colloid, or an aqueous suspension.

[0278] In some embodiments, the phenyl azide-based copolymer is a compound of formula (II) or (III) described herein.

[0279] In some embodiments, the mixture including the charged or zwitterionic copolymer has a concentration of the charged or zwitterionic copolymer in the mixture of between 1 mg / mL and 30 mg / mL.

[0280] In some embodiments, the concentration of the charged or zwitterionic copolymer in the mixture is from 0.1 mg / mL to 100 mg / mL, from 0.5 mg / mL to 50 mg / mL, from 1 mg / mL to 25 mg / mL, from 1 mg / mL to 20 mg / mL, from 1 mg / mL to 15 mg / mL, from 1 mg / mL to 10 mg / mL, from 1 mg / mL to 5 mg / mL, from 5 mg / mL to 30 mg / mL, from 5 mg / mL to 25 mg / mL, from 5 mg / mL to 2 0mg / mL, 5mg / mL~15mg / mL, 5mg / mL~10mg / mL, 10mg / mL~30mg / mL, 10mg / mL~25mg / mL, 10mg / mL~20mg / mL, 10mg / mL~ 15mg / mL, 15mg / mL~30mg / mL, 15mg / mL~25mg / mL, 15mg / mL~20mg / mL, 20mg / mL~30mg / mL, or 20mg / mL~25mg / mL. In some embodiments, the concentration of the charged or zwitterionic copolymer in the mixture is between 25 mg / mL and 30 mg / mL, between 30 mg / mL and 35 mg / mL, between 35 mg / mL and 40 mg / mL, between 40 mg / mL and 45 mg / mL, between 45 mg / mL and 50 mg / mL, between 50 mg / mL and 55 mg / mL, between 55 mg / mL and 60 mg / mL, between 60 mg / mL and 65 mg / mL, between 65 mg / mL and 70 mg / mL, between 70 mg / mL and 75 mg / mL, between 75 mg / mL and 80 mg / mL, between 80 mg / mL and 85 mg / mL, between 85 mg / mL and 90 mg / mL, between 90 mg / mL and 95 mg / mL, or between 95 mg / mL and 100 mg / mL.

[0281] In some embodiments, the concentration of the charged or zwitterionic copolymer in the mixture is about 1 mg / mL, 2 mg / mL, 3 mg / mL, 4 mg / mL, 5 mg / mL, 6 mg / mL, 7 mg / mL, 8 mg / mL, 9 mg / mL, 10 mg / mL, 11 mg / mL, 12 mg / mL, 13 mg / mL, 14 mg / mL, 15 mg / mL, 16 mg / mL, 17 mg / mL, 18 mg / mL, 19 mg / mL, 20 mg / mL, 21 mg / mL, 22 mg / mL, 23 mg / mL, 24 mg / mL, 25 mg / mL, 26 mg / mL, 27 mg / mL, 28 mg / mL, 29 mg / mL, or 30 mg / mL. In some embodiments, the concentration of the charged or zwitterionic copolymer in the mixture is about 31 mg / mL, 32 mg / mL, 33 mg / mL, 34 mg / mL, 35 mg / mL, 36 mg / mL, 37 mg / mL, 38 mg / mL, 39 mg / mL, 40 mg / mL, 41 mg / mL, 42 mg / mL, 43 mg / mL, 44 mg / mL, 45 mg / mL, 46 mg / mL, 47 mg / mL, 48 mg / mL, 49 mg / mL, 50 mg / mL, 51 mg / mL, 52 mg / mL, 53 mg / mL, 54 mg / mL, 55 mg / mL, 56 mg / mL, 57 mg / mL, 58 mg / mL, 59 mg / mL, or 60 mg / mL.

[0282] In some embodiments, the concentration of the charged or zwitterionic copolymer is 0.01-10 mg per square centimeter of the device. In some embodiments, the concentration of the charged or zwitterionic copolymer is 0.1-1 mg per square centimeter of the device. In some embodiments, the concentration of the charged or zwitterionic copolymer is 0.01-0.05, 0.1-0.2, 0.2-0.3, 0.3-0.4, 0.4-0.5, 0.5-0.6, 0.6-0.7, 0.7-0.8, 0.8-0.9, 0.9-1, 1-2, 2-2, 3-2, 4-2, 5-2, 6-2, 7-2, 8-2, or 9-10 per square centimeter of the device.

[0283] In some embodiments, the device comprises a polymer-based device. In some embodiments, the polymer-based device comprises a polyolefinic device. In some embodiments, the polyolefinic device comprises a device modified with polyethylene (PE), polypropylene (PP), polyamide (PA), polytetrafluoroethylene (PTFE), polyvinylidene fluoride (PVdF), polyvinyl chloride (PVC), or combinations thereof. In some embodiments, the device comprises a microporous device or a non-woven device. In some embodiments, the device comprises a carbon-based device comprising a moiety capable of binding with a compound having a structure of formula (I), (II), or (III). In some embodiments, the device comprises a carbon-based device comprising a moiety capable of binding with a copolymer comprising repeat units of formula (VII), (VIII), and (IX). In some embodiments, the carbon-based device comprises a polymeric moiety. In some embodiments, the carbon-based device comprises a carbon-based polymer. In some embodiments, the carbon-based device comprises a polyolefinic moiety. In some embodiments, the polyolefin portion comprises a polyethylene (PE) portion, a polypropylene (PP) portion, a polyamide (PA) portion, a polytetrafluoroethylene (PTFE) portion, a polyvinylidene fluoride (PVdF) portion, or a polyvinyl chloride (PVC) portion.

[0284] In some embodiments, the device comprises a carbon-based device. In some embodiments, the carbon-based device comprises a carbon-based polymer. In some embodiments, the carbon-based device comprises a polyolefin portion. In some embodiments, the polyolefin portion comprises a polyethylene portion, a polypropylene portion, a polyvinyl chloride portion, a polyvinylidene fluoride portion, a polytetrafluoroethylene portion, a polychlorotrifluoroethylene portion, or a polystyrene portion. In some embodiments, the carbon-based polymer comprises a polyamide portion, a polyurethane portion, a phenol-formaldehyde resin portion, a polycarbonate portion, a polychloroprene portion, a polyacrylonitrile portion, a polyimide portion, or a polyester portion. In some embodiments, the carbon-based polymer comprises nylon. In some embodiments, the carbon-based polymer comprises polyethylene terephthalate.

[0285] In some embodiments, the device comprises a silicon-based device. In some embodiments, the silicon-based device comprises a silicon-based polymer portion. In some embodiments, the device comprises a silicon-based device comprising a portion capable of bonding with a compound having the structure of formula (I), (II), or (III). In some embodiments, the device comprises a silicon-based device comprising a portion capable of bonding with a copolymer comprising repeating units of formula (VII), (VIII), and (IX). In some embodiments, the silicon-based device comprises a polymer portion. In some embodiments, the silicon-based device comprises a siloxane polymer portion, a sesquisiloxane polymer portion, a siloxane-silarylene polymer portion, a silakylene polymer portion, a polysilane portion, a polysilylene portion, or a polysilazane portion.

[0286] In some embodiments, the silicon based device comprises a siloxane polymer portion. In some embodiments, the silicon based device comprises a silicone polymer.

[0287] In some embodiments, the device comprises a carbon-based device or a silicon-based device.

[0288] In some embodiments, the copolymer comprises a zwitterionic copolymer. In some embodiments, the zwitterionic copolymer comprises polysulfobetaine.

[0289] In some embodiments, the biofouling of the biofouling resistant medical devices described herein is caused by bacteria, viruses, and / or fungi.

[0290] V. Synthesis method Methods provided by the present disclosure also include a method of synthesizing a compound of formula (II), the method comprising reacting a compound of formula (IV), or a salt or solvate thereof, with a compound of formula (V): [ka] During the ceremony, Each R 1a and R 1b is independently selected from hydrogen and halogen; Each R 2a and R 2b are independently selected from halogen, -CN, and optionally substituted C 1 -C 6 fluoroalkyl; Each A 1 , A 2 , and A 3 are independently -C(=O)-, -S(=O)-, -S(=O) 2 - and -S(=O)(=NR 3c )- is selected from Each B 1 , B 2 , and B. 3 are independently -O- and -NR 3c - selected from D is -S(=O) 2 O - , -S(=O) 2 OR 9a , -C(=O)O - , or -C(=O)OR 9a and Z 1is -(CR 6c R 6d ) s - and Z 2 is -(CR 6c R 6d ) t - and Z 3 is -(CR 6c R 6d ) p - and Each R 3a and R 3b are independently hydrogen, optionally substituted C 1 -C 4 alkyl, and optionally substituted benzyl; Each R 4c , R 4d , R 5d , R 5e , R 6c , and R 6d are independently hydrogen, halogen, -CN, -OH, optionally substituted C 1 -C 4 Alkyl, optionally substituted C 1 -C 4 Fluoroalkyl, optionally substituted C 2 -C 6 Alkenyl, -NR 3c R 3d , -S(=O) 2 O - , -S(=O) 2 OR 9a , -C(=O)O - , and -C(=O)OR 9a is selected from Each R 3c and R 3d are independently hydrogen, optionally substituted C 1 -C 4 Alkyl, -X-optionally substituted C 1 -C 4 Alkyl, optionally substituted C 2 -C 6 alkenyl, and optionally substituted aryl; X is -C(=O)-, -S(=O)-, or -S(=O) 2 - and Each R 9a , R 11a , R 11b , R 11c , R 12a , R 12b , and R 12c are independently hydrogen, optionally substituted C 1 -C 4 alkyl, and optionally substituted aryl; n is an integer selected from 0, 1, 2, 3, 4, 5, 6, 7, and 8; s is an integer selected from 1, 2, 3, 4, or 5; t is an integer selected from 1, 2, 3, 4, or 5; p is an integer selected from 1, 2, 3, 4, or 5; 0 <x<1であり、 The compounds of formula (II) and formula (V) are each charged or zwitterionic.

[0291] In some embodiments, the compound of formula (II) is [ka] isn't it.

[0292] In some embodiments, x in formula (II) is not about 0.9434.

[0293] In some embodiments, the compound of formula (II) is not obtained by using 2 g of sulfobetaine methacrylate monomer and 156 mg of perfluorophenyl azide methacrylamide monomer.

[0294] In some embodiments, the different variables of the compound of formula (II) are as described above.

[0295] In some embodiments, the compound of formula (IV) has the structure: [ka]

[0296] In some embodiments, the compound of formula (V) has the structure: [ka]

[0297] Methods provided by the present disclosure also include a method of synthesizing a compound of formula (III), the method comprising reacting a compound of formula (IV), or a salt or solvate thereof, with a compound of formula (VI): [ka] During the ceremony, Each R 1a and R 1b is independently selected from hydrogen and halogen; Each R 2a and R 2b are independently selected from halogen, -CN, and optionally substituted C 1 -C 6 fluoroalkyl; Each A 1 , A 2 , and A 3 are independently -C(=O)-, -S(=O)-, -S(=O) 2 - and -S(=O)(=NR 3c )- is selected from Each B 1 , B 2 , and B. 3 are independently -O- and -NR 3c - selected from Z 1 is -(CR 6c R 6d ) s - and Z 2 is -(CR 6c R 6d ) t - and E is -CN, -OR9a , -NR 9a R 9b , -NR 9a R 9b R 9c+ , optionally substituted C 1 -C 4 Alkyl, optionally substituted C 1 -C 6 Fluoroalkyl, -S(=O) 2 O - , -S(=O) 2 OR 9a , -C(=O)O - , or -C(=O)OR 9a and Each R 4c , R 4d , R 5d , R 5e , R 6c , and R 6d are independently hydrogen, halogen, -CN, -OR 9a , optionally substituted C 1 -C 4 Alkyl, optionally substituted C 1 -C 4 Fluoroalkyl, optionally substituted C 2 -C 6 Alkenyl, -NR 3c R 3d , -S(=O) 2 O - , -S(=O) 2 OR 9a , -C(=O)O - , and -C(=O)OR 9a is selected from Each R 3c and R 3d are independently hydrogen, optionally substituted C 1 -C 4 Alkyl, -X-optionally substituted C 1 -C 4 Alkyl, optionally substituted C 2 -C 6 alkenyl, and optionally substituted aryl; X is -C(=O)-, -S(=O)-, or -S(=O)2 - and Each R 9a , R 9b , R 9c , R 11a , R 11b , R 11c , R 12a , R 12b , and R 12c are independently hydrogen, optionally substituted C 1 -C 4 alkyl, and optionally substituted aryl; n is an integer selected from 0, 1, 2, 3, 4, 5, 6, 7, and 8; s is an integer selected from 1, 2, 3, 4, or 5; t is an integer selected from 1, 2, 3, 4, or 5; 0 <x<1である。

[0298] In some embodiments, the compounds of formula (III) and formula (VI) are each charged or zwitterionic. In some embodiments, the compound of formula (VI) comprises a positively charged compound of formula (VI). In some embodiments, the compound of formula (VI) comprises a negatively charged compound of formula (VI). In some embodiments, the compound of formula (III) comprises a positively charged repeat unit. In some embodiments, the compound of formula (III) comprises a negatively charged repeat unit. In some embodiments, the compound of formula (III) comprises a positively charged repeat unit and a negatively charged repeat unit. In some embodiments, the ratio of the positively charged repeat unit to the negatively charged repeat unit in the compound of formula (III) is about 10:1 to about 1:10. In some embodiments, the ratio of the positively charged repeat unit to the negatively charged repeat unit in the compound of formula (III) is about 5:1 to about 1:5. In some embodiments, the ratio of the positively charged repeat unit to the negatively charged repeat unit in the compound of formula (III) is about 2:1 to about 1:2. In some embodiments, the ratio of positively charged repeat units to negatively charged repeat units in the compound of formula (III) is about 1:1.

[0299] In some embodiments, the different variables of the compound of formula (III) are as described above.

[0300] In some embodiments, the compound of formula (IV) has the structure: [ka]

[0301] In some embodiments, the compound of formula (VI) has the structure: [ka]

[0302] In some embodiments, the compound of formula (VI) has the structure: [ka]

[0303] Any combination of the groups described above or below for the various variables is contemplated herein. Throughout the specification, groups and substituents thereof are chosen by one of ordinary skill in the art to provide stable moieties and compounds.

[0304] Anti-biofouling coating properties In some embodiments, the anti-biofouling coatings disclosed herein have a variety of properties that provide superior functionality of the device, including superior flux, improved hydrophilicity, improved resistance to fouling, tunable surface charge properties, greater thermal stability, greater chemical stability, greater solvent stability, or a combination thereof. It is understood that the coatings disclosed herein may also have other properties.

[0305] In some embodiments, the biofouling resistant coatings disclosed herein have a water receding angle of less than about 70°. In some embodiments, the biofouling resistant coatings disclosed herein have a water receding angle of less than about 65°. In some embodiments, the biofouling resistant coatings disclosed herein have a water receding angle of less than about 60°. In some embodiments, the biofouling resistant coatings disclosed herein have a water receding angle of less than about 55°. In some embodiments, the biofouling resistant coatings disclosed herein have a water receding angle of less than about 50°. In some embodiments, the biofouling resistant coatings disclosed herein have a water receding angle of less than about 45°. In some embodiments, the biofouling resistant coatings disclosed herein have a water receding angle of less than about 40°. In some embodiments, the biofouling resistant coatings disclosed herein have a water receding angle of less than about 35°. In some embodiments, the biofouling resistant coatings disclosed herein have a water receding angle of less than about 30°. In some embodiments, the biofouling resistant coatings disclosed herein have a water receding angle of less than about 25°. In some embodiments, the anti-biofouling coatings disclosed herein have a water receding angle of less than about 20°. In some embodiments, the anti-biofouling coatings disclosed herein have a water receding angle of less than about 15°. In some embodiments, the anti-biofouling coatings disclosed herein have a water receding angle of less than about 10°. In some embodiments, the anti-biofouling coatings disclosed herein have a water receding angle of less than about 5°. In some embodiments, the anti-biofouling coatings disclosed herein have a water receding angle of about 0°. In certain embodiments, the devices provided herein coated with one or more anti-biofouling coatings described herein have high fouling resistance.

[0306] In further aspects, the anti-biofouling coatings disclosed herein exhibit an improvement in at least one property selected from resistance to fouling, hydrophilicity, surface charge, salt rejection, and roughness. In some embodiments, the anti-biofouling coatings disclosed herein exhibit an improvement in at least one property selected from resistance to fouling, salt rejection, and hydrophilicity. In some embodiments, the anti-biofouling coatings disclosed herein exhibit an improvement in resistance to fouling. In some embodiments, the anti-biofouling coatings disclosed herein exhibit an improvement in hydrophilicity. In some embodiments, the anti-biofouling coatings disclosed herein exhibit an improvement in surface charge. In some embodiments, the anti-biofouling coatings disclosed herein exhibit an improvement in roughness. In some embodiments, the anti-biofouling coatings disclosed herein exhibit reduced surface roughness. In some embodiments, the anti-biofouling coatings disclosed herein exhibit an improvement in salt rejection.

[0307] In some embodiments, the anti-biofouling coatings disclosed herein, including one or more compounds of formula (I), (II), or (III) as described herein, prevent and / or reduce biofouling. In some embodiments, the anti-biofouling coatings disclosed herein, including one or more copolymers including repeating units of formula (VII), (VIII), and (IX) as described herein, prevent and / or reduce biofouling. In some cases, biofouling includes micro- or macro-biofouling. Micro-biofouling includes microbial adhesion (e.g., bacterial adhesion) and / or the formation of a biofilm. A biofilm is a group of microorganisms that adhere to a surface. In some cases, the attached microorganisms are further embedded in a self-produced matrix of extracellular polymeric material, including extracellular DNA, proteins, and polymeric agglomerates of polysaccharides. Macro-biofouling includes the attachment of larger organisms. In some cases, the anti-biofouling coatings disclosed herein prevent and / or reduce micro-biofouling. In some cases, the anti-biofouling coatings disclosed herein prevent and / or reduce bacterial adhesion. In some cases, the anti-biofouling coatings disclosed herein prevent and / or reduce biofilms. In some cases, the anti-biofouling coatings disclosed herein prevent and / or reduce macro-biofouling. Microbiofouling

[0308] In some cases, the microbiofouling is formed by bacteria or fungi. In some cases, the microbiofouling is formed by bacteria. In some cases, the bacteria is a gram-positive or gram-negative bacteria. In some cases, the bacteria is a marine bacteria.

[0309] In some cases, the microbiofouling is formed by gram-positive bacteria. Exemplary gram-positive bacteria include, but are not limited to, bacteria from the genus Actinomyces, Arthrobacter, Bacillus, Clostridium, Corynebacterium, Enterococcus, Lactococcus, Listeria, Micrococcus, Mycobacterium, Staphylococcus, or Streptococcus. In some cases, the gram-positive bacteria include Actinomyces spp., Arthrobacter spp., Bacillus licheniformis, Clostridium difficile, Clostridium spp., Corynebacterium spp., Enterococcus faecalis, Lactococcus spp., Listeria monocytogenes, Micrococcus spp., Mycobacterium spp., Staphylococcus aureus, Staphylococcus epidermidis, Streptococcus pneumoniae, or Streptococcus pyogenes.

[0310] In some cases, the biofouling is formed by gram-positive bacteria from the genus Actinomyces, Arthrobacter, Bacillus, Clostridium, Corynebacterium, Enterococcus, Lactococcus, Listeria, Micrococcus, Mycobacterium, Staphylococcus, or Streptococcus. In some cases, biofouling is formed by gram-positive bacteria such as Actinomyces spp., Arthrobacter spp., Bacillus licheniformis, Clostridium difficile, Clostridium spp., Corynebacterium spp., Enterococcus faecalis, Lactococcus spp., Listeria monocytogenes, Micrococcus spp., Mycobacterium spp., Staphylococcus aureus, Staphylococcus epidermidis, Streptococcus pneumoniae, or Streptococcus pyogenes.

[0311] In some cases, the anti-biofouling coating disclosed herein is resistant to fouling. In some cases, the anti-biofouling coating disclosed herein prevents and / or reduces micro-biofouling on one or more of its surfaces. In some cases, the anti-biofouling coating disclosed herein prevents and / or reduces micro-biofouling formed by gram-positive bacteria from the genus Actinomyces, Arthrobacter, Bacillus, Clostridium, Corynebacterium, Enterococcus, Lactococcus, Listeria, Micrococcus, Mycobacterium, Staphylococcus, or Streptococcus. In some cases, the anti-biofouling coatings disclosed herein prevent and / or reduce micro-biofouling formed by gram-positive bacteria, such as Actinomyces spp., Arthrobacter spp., Bacillus licheniformis, Clostridium difficile, Clostridium spp., Corynebacterium spp., Enterococcus faecalis, Lactococcus spp., Listeria monocytogenes, Micrococcus spp., Mycobacterium spp., Staphylococcus aureus, Staphylococcus epidermidis, Streptococcus pneumoniae, or Streptococcus pyogenes.

[0312] In some cases, biofouling includes bacterial adhesion. In some cases, the anti-biofouling coatings disclosed herein prevent and / or reduce bacterial adhesion. In some cases, the anti-biofouling coatings disclosed herein prevent and / or reduce bacterial adhesion formed by gram-positive bacteria from the genus Actinomyces, Arthrobacter, Bacillus, Clostridium, Corynebacterium, Enterococcus, Lactococcus, Listeria, Micrococcus, Mycobacterium, Staphylococcus, or Streptococcus. In some cases, the anti-biofouling coatings disclosed herein applied to a material prevent and / or reduce bacterial adhesion formed by gram-positive bacteria, such as Actinomyces spp., Arthrobacter spp., Bacillus licheniformis, Clostridium difficile, Clostridium spp., Corynebacterium spp., Enterococcus faecalis, Lactococcus spp., Listeria monocytogenes, Micrococcus spp., Mycobacterium spp., Staphylococcus aureus, Staphylococcus epidermidis, Streptococcus pneumoniae, or Streptococcus pyogenes.

[0313] In some cases, biofouling includes biofilms. In some cases, the anti-biofouling coatings disclosed herein coated on a material prevent and / or reduce biofilms. In some cases, the anti-biofouling coatings disclosed herein coated on a material prevent and / or reduce biofilms formed by gram-positive bacteria from the genus Actinomyces, Arthrobacter, Bacillus, Clostridium, Corynebacterium, Enterococcus, Lactococcus, Listeria, Micrococcus, Mycobacterium, Staphylococcus, or Streptococcus. In some cases, the anti-biofouling coatings disclosed herein applied to a material prevent and / or reduce biofilms formed by gram-positive bacteria, such as Actinomyces spp., Arthrobacter spp., Bacillus licheniformis, Clostridium difficile, Clostridium spp., Corynebacterium spp., Enterococcus faecalis, Lactococcus spp., Listeria monocytogenes, Micrococcus spp., Mycobacterium spp., Staphylococcus aureus, Staphylococcus epidermidis, Streptococcus pneumoniae, or Streptococcus pyogenes.

[0314] In some cases, the microbiofouling is formed by gram-negative bacteria. Exemplary gram-negative bacteria include, but are not limited to, bacteria from the genera Alteromonas, Aeromonas, Desulfovibrio, Escherichia, Fusobacterium, Geobacter, Haemophilus, Klebsiella, Legionella, Porphyromonas, Proteus, Pseudomonas, Serratia, Shigella, Salmonella, or Vibrio. In some cases, Gram-negative bacteria include Alteromonas spp., Aeromonas spp., Desulfovibrio spp., Escherichia coli, Fusobacterium nucleatum, Geobacter spp., Haemophilus spp., Klebsiella spp., Legionella pneumophila, Porphyromonas spp., Pseudomonas aeruginosa, Proteus vulgaris, Proteus mirabilis, Proteus penneri, Serratia spp., Shigella dysenteriae, Shigella flexneri, Shigella boydii, Shigella sonnei, Salmonella bongori, Salmonella enterica, or Vibrio Cholerae.

[0315] In some cases, microbiofouling is formed by gram-negative bacteria from the genera Alteromonas, Aeromonas, Desulfovibrio, Escherichia, Fusobacterium, Geobacter, Haemophilus, Klebsiella, Legionella, Porphyromonas, Proteus, Pseudomonas, Serratia, Shigella, Salmonella, or Vibrio. In some cases, microbiofouling is formed by gram-negative bacteria such as Alteromonas spp., Aeromonas spp., Desulfovibrio spp., Escherichia coli, Fusobacterium nucleatum, Geobacter spp., Haemophilus spp., Klebsiella spp., Legionella pneumophila, Porphyromonas spp., Pseudomonas aeruginosa, Proteus vulgaris, Proteus mirabilis, Proteus penneri, Serratia spp., Shigella dysenteriae, Shigella flexneri, Shigella boydii, Shigella sonnei, Salmonella bongori, Salmonella enterica, or Vibrio Cholerae.

[0316] In some embodiments, the anti-biofouling coatings disclosed herein prevent and / or reduce micro-biofouling formed by gram-negative bacteria from the genera Alteromonas, Aeromonas, Desulfovibrio, Escherichia, Fusobacterium, Geobacter, Haemophilus, Klebsiella, Legionella, Porphyromonas, Proteus, Pseudomonas, Serratia, Shigella, Salmonella, or Vibrio. In some cases, the anti-biofouling coatings disclosed herein prevent and / or reduce microbiofouling formed by gram-negative bacteria, such as Alteromonas spp., Aeromonas spp., Desulfovibrio spp., Escherichia coli, Fusobacterium nucleatum, Geobacter spp., Haemophilus spp., Klebsiella spp., Legionella pneumophila, Porphyromonas spp., Pseudomonas aeruginosa, Proteus vulgaris, Proteus mirabilis, Proteus penneri, Serratia spp., Shigella dysenteriae, Shigella flexneri, Shigella boydii, Shigella sonnei, Salmonella bongori, Salmonella enterica, or Vibrio Cholerae.

[0317] In some embodiments, microbiofouling comprises bacterial adhesion. In some embodiments, the anti-biofouling coatings disclosed herein prevent and / or reduce bacterial adhesion formed by gram-negative bacteria from the genera Alteromonas, Aeromonas, Desulfovibrio, Escherichia, Fusobacterium, Geobacter, Haemophilus, Klebsiella, Legionella, Porphyromonas, Proteus, Pseudomonas, Serratia, Shigella, Salmonella, or Vibrio. In some cases, the anti-biofouling coatings disclosed herein prevent and / or reduce bacterial adhesion formed by gram-negative bacteria, such as Alteromonas spp., Aeromonas spp., Desulfovibrio spp., Escherichia coli, Fusobacterium nucleatum, Geobacter spp., Haemophilus spp., Klebsiella spp., Legionella pneumophila, Porphyromonas spp., Pseudomonas aeruginosa, Proteus vulgaris, Proteus mirabilis, Proteus penneri, Serratia spp., Shigella dysenteriae, Shigella flexneri, Shigella boydii, Shigella sonnei, Salmonella bongori, Salmonella enterica, or Vibrio Cholerae.

[0318] In some cases, the microbiofouling comprises a biofilm. In some embodiments, the anti-biofouling coatings disclosed herein prevent and / or reduce biofilms formed by gram-negative bacteria from the genera Alteromonas, Aeromonas, Desulfovibrio, Escherichia, Fusobacterium, Geobacter, Haemophilus, Klebsiella, Legionella, Porphyromonas, Proteus, Pseudomonas, Serratia, Shigella, Salmonella, or Vibrio. In some cases, the anti-biofouling coatings disclosed herein prevent and / or reduce biofilms formed by gram-negative bacteria, such as Alteromonas spp., Aeromonas spp., Desulfovibrio spp., Escherichia coli, Fusobacterium nucleatum, Geobacter spp., Haemophilus spp., Klebsiella spp., Legionella pneumophila, Porphyromonas spp., Pseudomonas aeruginosa, Proteus vulgaris, Proteus mirabilis, Proteus penneri, Serratia spp., Shigella dysenteriae, Shigella flexneri, Shigella boydii, Shigella sonnei, Salmonella bongori, Salmonella enterica, or Vibrio Cholerae.

[0319] In some cases, the microbiofouling is formed by marine bacteria. In some cases, the marine bacteria includes Pseudoalteromonas spp. or Shewanella spp. In some cases, the microbiofouling is formed by Pseudoalteromonas spp. or Shewanella spp.

[0320] In some embodiments, the anti-biofouling coatings disclosed herein prevent and / or reduce micro-biofouling formed by marine bacteria. In some cases, the anti-biofouling coatings disclosed herein prevent and / or reduce micro-biofouling formed by Pseudoalteromonas spp. or Shewanella spp.

[0321] In some cases, the microbiofouling comprises bacterial adhesion. In some embodiments, the anti-biofouling coatings disclosed herein prevent and / or reduce bacterial adhesion formed by marine bacteria. In some cases, the anti-biofouling coatings disclosed herein prevent and / or reduce bacterial adhesion formed by Pseudoalteromonas spp. or Shewanella spp.

[0322] In some cases, the microbiofouling comprises a biofilm. In some embodiments, the anti-biofouling coatings disclosed herein prevent and / or reduce biofilms formed by marine bacteria. In some cases, the anti-biofouling coatings disclosed herein prevent and / or reduce biofilms formed by Pseudoalteromonas spp. or Shewanella spp.

[0323] In some embodiments, the microbiofouling is formed by a fungus. Exemplary fungi include, but are not limited to, Candida albicans, Candida glabrata, Candida rugose, Candida parapsilosis, Candida tropicalis, Candida dubliniensis, or Hormoconis resinae. In some cases, the microbiofouling is formed by Candida albicans, Candida glabrata, Candida rugose, Candida parapsilosis, Candida tropicalis, Candida dubliniensis, or Hormoconis resinae.

[0324] In some embodiments, the anti-biofouling coatings disclosed herein prevent and / or reduce micro-biofouling formed by fungi. In some cases, the anti-biofouling coatings disclosed herein prevent and / or reduce micro-biofouling formed by Candida albicans, Candida glabrata, Candida rugose, Candida parapsilosis, Candida tropicalis, Candida dubliniensis, or Hormoconis resinae.

[0325] In some cases, the microbiofouling comprises bacterial adhesion. In some embodiments, the anti-biofouling coatings disclosed herein prevent and / or reduce bacterial adhesion formed by fungi. In some cases, the anti-biofouling coatings disclosed herein prevent and / or reduce bacterial adhesion formed by Candida albicans, Candida glabrata, Candida rugose, Candida parapsilosis, Candida tropicalis, Candida dubliniensis, or Hormoconis resinae.

[0326] In some cases, the microbiofouling comprises a biofilm. In some embodiments, the anti-biofouling coatings disclosed herein prevent and / or reduce biofilms formed by fungi. In some cases, the anti-biofouling coatings disclosed herein prevent and / or reduce biofilms formed by Candida albicans, Candida glabrata, Candida rugose, Candida parapsilosis, Candida tropicalis, Candida dubliniensis, or Hormoconis resinae.

[0327] Macro biofouling In some embodiments, the macrobiofouling includes calcareous or non-calcareous fouling organisms. Calcareous fouling organisms are organisms with hard bodies. In some cases, calcareous fouling organisms include barnacles, bryozoans, mollusks, polychaetes, tube worms, or zebra mussels. Non-calcareous fouling organisms include mollusks. Non-calcareous fouling organisms include seaweeds, hydrozoans, or algae.

[0328] In some cases, macro-biofouling is formed by calcareous fouling organisms. In some cases, macro-biofouling is formed by barnacles, bryozoans, mollusks, polychaetes, tube worms, or zebra mussels.

[0329] In some embodiments, the anti-biofouling coatings disclosed herein prevent and / or reduce macro-biofouling formed by calcareous fouling organisms. In some cases, the anti-biofouling coatings disclosed herein prevent and / or reduce macro-biofouling formed by barnacles, bryozoans, mollusks, polychaetes, tubeworms, or zebra mussels.

[0330] In some cases, the macro-biofouling is formed by non-calcareous fouling organisms, hi some cases, the macro-biofouling is formed by seaweeds, hydrozoans, or algae.

[0331] Also disclosed herein in some embodiments are anti-biofouling coatings that prevent and / or reduce macro-biofouling formed by non-calcareous fouling organisms. In some cases, the anti-biofouling coatings disclosed herein prevent and / or reduce macro-biofouling formed by seaweed, hydroxides, or algae.

[0332] In some embodiments, the anti-biofouling coating disclosed herein reduces the formation of biofouling on its surface. In some cases, the formation of biofouling on the surface of a device modified with a compound of formula (I), (II), or (III) is reduced by about 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80%, 90%, 95%, 99%, 99.5%, 99.9% or more compared to the unmodified surface of the device. In some cases, the formation of biofouling on the surface of a device modified with a copolymer comprising repeating units of formula (VII), (VIII), and (IX) is reduced by about 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80%, 90%, 95%, 99%, 99.5%, 99.9% or more compared to the unmodified surface of the device. In some cases, the formation of biofouling is reduced by at least about 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80%, 90%, 95%, 99%, 99.5%, 99.9%, or more, compared to the unmodified surface of the device. In some cases, the formation of biofouling on the unmodified surface of the device is determined by comparing the amount of biofouling after a period of storage, use, and / or testing of the device. For example, the devices can be tested by exposing them to conditions conducive to biofouling formation (e.g., in vitro biofouling testing techniques known and practiced in the art). In some cases, the formation of biofouling is reduced by about 10% or more, compared to the unmodified surface of the device. In some cases, the formation of biofouling is reduced by about 20% or more, compared to the unmodified surface of the device. In some cases, the formation of biofouling is reduced by about 30% or more, compared to the unmodified surface of the device. In some cases, the formation of biofouling is reduced by about 40% or more compared to the unmodified surface of the device. In some cases, the formation of biofouling is reduced by about 50% or more compared to the unmodified surface of the device. In some cases, the formation of biofouling is reduced by about 60% or more compared to the unmodified surface of the device. In some cases, the formation of biofouling is reduced by about 70% or more compared to the unmodified surface of the device.In some cases, the formation of biofouling is reduced by about 80% or more compared to the unmodified surface of the device. In some cases, the formation of biofouling is reduced by about 90% or more compared to the unmodified surface of the device. In some cases, the formation of biofouling is reduced by about 95% or more compared to the unmodified surface of the device. In some cases, the formation of biofouling is reduced by about 99% or more compared to the unmodified surface of the device. In some cases, the formation of biofouling is reduced by about 99.5% or more compared to the unmodified surface of the device. In some cases, the formation of biofouling is reduced by about 99.9% or more compared to the unmodified surface of the device.

[0333] In some embodiments, the anti-biofouling coatings disclosed herein are further coated with an additional agent. In some cases, the additional agent is an antimicrobial agent. Exemplary antimicrobial agents include quaternary ammonium salts or tertiary amines. In some cases, the additional agent is a chemical germicide. Exemplary chemical germicides include sodium hypochlorite, sodium hydroxide, and benzalkonium chloride.

[0334] definition As used herein, nomenclature for compounds, including organic compounds, may be given using common names, IUPAC, IUBMB, or CAS nomenclature recommendations. When one or more stereochemical features are present, the Cahn-Ingold-Prelog rules for stereochemistry may be used to specify stereochemical priority, E / Z specifications, etc. One of skill in the art can readily ascertain the structure of a compound when a name is given, either by systematic reduction of the compound structure using the naming rules, or by commercially available software such as CHEMDRAW™ (Cambridgesoft Corporation, USA).

[0335] As used in this specification and the appended claims, the singular forms "a," "an," and "the" include plural referents unless the context clearly dictates otherwise. Thus, for example, reference to "a component," "a polymer," or "a particle" includes a mixture of two or more such components, polymers, or particles, etc.

[0336] Ranges can be expressed herein as from "about" one particular value and / or to "about" another particular value. When such a range is expressed, another aspect includes from the one particular value and / or to the other particular value. Similarly, by use of the preposition "about," when values ​​are expressed as approximations, it will be understood that the particular value forms another aspect. It will be further understood that each of the endpoints of a range is significant both in relation to the other endpoint, and independently of the other endpoint. It is also understood that there are several values ​​disclosed herein, and that each value is also disclosed herein as "about" that particular value in addition to the value itself. For example, if the value "10" is disclosed, then "about 10" is also disclosed. In some embodiments, the term "about" includes amounts that are expected to be within experimental error. It is also understood that when a value is disclosed, the value "less than or equal to," the value "greater than or equal to," and possible ranges between the values ​​are also disclosed as would be appropriately understood by one of ordinary skill in the art. For example, if the value "10" is disclosed, then "less than or equal to 10" and "greater than or equal to 10" are also disclosed. It is also understood that throughout this application, data is provided in several different formats, and that this data represents endpoints and starting points, as well as ranges for any combination of the data points. For example, if a specific data point "10" and a specific data point 15 are disclosed, it is understood that greater than, greater than, less than, less than, and equal to 10 and 15, as well as 10 to 15, are considered to be disclosed. It is also understood that each unit between two specific units is also disclosed. For example, if 10 and 15 are disclosed, then 11, 12, 13, and 14 are also disclosed.

[0337] References in this specification and in the concluding claims to parts by weight of a particular element or component in a composition indicate the weight relationship between the element or component and any other element or component in the composition or article for which the parts by weight are expressed. Thus, in a compound containing 2 parts by weight of component X and 5 parts by weight of component Y, X and Y are present in a weight ratio of 2:5, and are present in such ratio regardless of whether additional components are included in the compound.

[0338] Unless specifically stated to the contrary, weight percent (wt %) of a component is based on the total weight of the formulation or composition in which the component is included.

[0339] As used herein, the terms "any" or "optionally" mean that the subsequently described event or circumstance may or may not occur, and that the description includes instances when the event or circumstance occurs and instances when the event or circumstance does not occur.

[0340] As used herein, the terms "effective amount" and "amount effective" refer to an amount sufficient to achieve a desired result or to affect an undesirable condition.

[0341] The term "stable," as used herein, refers to compositions that do not substantially change when subjected to conditions that permit their production, detection, and, in certain embodiments, their recovery, purification, and use for one or more of the purposes disclosed herein.

[0342] As used herein, the term "polymer" refers to a relatively high molecular weight organic compound, natural or synthetic, whose structure can be represented by small repeating unit monomers (e.g., polyethylene, rubber, cellulose). Synthetic polymers are typically formed by addition or condensation polymerization of monomers. Unless otherwise specified, polymer molecular weights are given in Daltons.

[0343] As used herein, the term "homopolymer" refers to a polymer formed from one type of repeating unit (monomer residues).

[0344] As used herein, the term "copolymer" refers to a polymer formed from two or more different repeat units (monomer residues). By way of example and without limitation, a copolymer can be an alternating copolymer, a random copolymer, a block copolymer, or a graft copolymer. In certain aspects, it is also contemplated that the various block segments of a block copolymer can themselves comprise copolymers. In some embodiments, the terms "copolymer" and "compound" are used interchangeably throughout this specification.

[0345] As used herein, the term "oligomer" refers to a relatively low molecular weight polymer having a number of repeat units from 2 to 10, e.g., from 2 to 8, from 2 to 6, or from 2 to 4. In one embodiment, an oligomeric assembly can have an average number of repeat units from about 2 to about 10, e.g., from about 2 to about 8, from about 2 to about 6, or from about 2 to about 4.

[0346] As used herein, the term "crosslinked polymer" refers to a polymer that has bonds connecting one polymer chain to another.

[0347] As used herein, the term "porogen composition" or "porogen" refers to any structural material that can be used to make a porous material.

[0348] "Oxo" refers to the =O substituent.

[0349] "Benzyl" is -CH 2 (C 6 H 5 ) substituent.

[0350] "Alkyl" refers to a straight or branched hydrocarbon chain radical having from 1 to 20 carbon atoms and attached to the remainder of the molecule by a single bond. Alkyl containing up to 10 carbon atoms is C 1 -C 10 Similarly, for example, an alkyl containing up to 6 carbon atoms is referred to as C 1 -C 6 Alkyl. Alkyl (and other moieties defined herein) containing other numbers of carbon atoms are represented similarly. Alkyl groups include, but are not limited to, C 1- C 10 Alkyl, C 1 -C 9 Alkyl, C 1 -C 8 Alkyl, C 1 -C 7 Alkyl, C 1 -C 6 Alkyl, C 1 -C 5 Alkyl, C 1 -C 4 Alkyl, C 1 -C 3 Alkyl, C 1 -C 2 Alkyl, C 2 -C 8 Alkyl, C 3 -C 8 Alkyl, and C 4 -C 8 Representative alkyl groups include, but are not limited to, methyl, ethyl, n-propyl, 1-methylethyl (i-propyl), n-butyl, i-butyl, s-butyl, n-pentyl, 1,1-dimethylethyl (t-butyl), 3-methylhexyl, 2-methylhexyl, 1-ethyl-propyl, and the like. In some embodiments, the alkyl is methyl or ethyl. In some embodiments, the alkyl is -CH(CH 3 ) 2 or -C(CH 3 ) 3 Unless stated otherwise in the specification, an alkyl group may be optionally substituted as described below.

[0351] "Alkylene" or "alkylene chain" refers to a straight or branched divalent hydrocarbon chain that connects the remainder of the molecule to a radical group. In some embodiments, alkylene is -CH 2 -, -CH 2 CH 2 -, or -CH 2 CH 2 CH 2 In some embodiments, alkylene is -CH 2 In some embodiments, alkylene is -CH 2 CH 2 In some embodiments, alkylene is -CH 2 CH 2 CH 2 In some embodiments, alkylene is -CH 2 C(CH 3 )CH 2 -It is.

[0352] "Alkoxy" refers to a radical of the formula -OR, where R is an alkyl radical as defined. Unless stated otherwise in the specification, an alkoxy group may be optionally substituted as described below. Representative alkoxy groups include, but are not limited to, methoxy, ethoxy, propoxy, butoxy, pentoxy. In some embodiments, an alkoxy is methoxy. In some embodiments, an alkoxy is ethoxy.

[0353] "Alkenyl" refers to a type of alkyl group in which at least one carbon-carbon double bond is present. In one embodiment, an alkenyl group has the formula -C(R a )=C(R a ) 2 wherein each R a refers to the remainder of the alkenyl group, which may be the same or different. In some embodiments, each R ais hydrogen or an alkyl group. In some embodiments, alkenyl is selected from ethenyl (i.e., vinyl), propenyl (i.e., allyl), butenyl, pentenyl, pentadienyl, and the like. Non-limiting examples of alkenyl groups include -CH=CH 2 , -C(CH 3 )=CH 2 , -CH=CHCH 3 , -C(CH 3 )=CHCH 3 , and -CH 2 CH=CH 2 Examples include:

[0354] "Heteroalkylene" refers to an alkyl radical as described above in which one or more carbon atoms of the alkyl has been replaced with an O, N, or S atom. "Heteroalkylene" or "heteroalkylene chain" refers to a straight or branched divalent heteroalkyl chain linking the remainder of the molecule to a radical group. Unless stated otherwise in the specification, a heteroalkyl or heteroalkylene group can be optionally substituted as described below. Representative heteroalkyl groups include -OCH 2 OMe, -OCH 2 CH 2 OMe, or -OCH 2 CH 2 OCH 2 CH 2 NH 2 Representative heteroalkylene groups include, but are not limited to, -OCH 2 CH 2 O-, -OCH 2 CH 2 OCH 2 CH 2 O-, or -OCH 2 CH 2 OCH 2 CH 2 OCH 2 CH 2 Examples include, but are not limited to, O-.

[0355] "Alkylamino" refers to a radical of the formula -NHR or -NRR where each R is independently an alkyl radical as defined above. Unless stated otherwise in the specification, an alkylamino group can be optionally substituted as described below.

[0356] The term "aromatic" refers to a planar ring having a delocalized π-electron system containing 4n+2 π-electrons, where n is an integer. An aromatic can be optionally substituted. The term "aromatic" includes both aryl groups (e.g., phenyl, naphthalenyl) and heteroaryl groups (e.g., pyridinyl, quinolinyl).

[0357] "Aryl" refers to an aromatic ring in which each of the atoms forming the ring is a carbon atom. An aryl group can be optionally substituted. Examples of aryl groups include, but are not limited to, phenyl and naphthyl. In some embodiments, an aryl is phenyl. Depending on the structure, an aryl group can be a monoradical or a diradical (i.e., an arylene group). Unless otherwise stated in the specification, the term "aryl" or the prefix "ar-" (e.g., as in "aralkyl") is meant to include aryl radicals that are optionally substituted.

[0358] "Carboxy" is -CO 2 H. In some embodiments, the carboxy moiety may be replaced with a "carboxylic acid bioisostere," which refers to a functional group or moiety that exhibits similar physical and / or chemical properties as a carboxylic acid moiety. A carboxylic acid bioisostere has similar biological properties as a carboxylic acid group. A compound having a carboxylic acid moiety can have a carboxylic acid moiety replaced with a carboxylic acid bioisostere and can have similar physical and / or biological properties when compared to a carboxylic acid-containing compound. For example, in one embodiment, a carboxylic acid bioisostere ionizes at approximately the same physiological pH as a carboxylic acid group. Examples of carboxylic acid bioisosteres include: [ka] These include, but are not limited to:

[0359] "Cycloalkyl" refers to a monocyclic or polycyclic non-aromatic radical in which each of the atoms forming the ring (i.e., skeletal atoms) is a carbon atom. Cycloalkyls can be saturated or partially unsaturated. Cycloalkyls can be fused to an aromatic ring (in which case the cycloalkyl is attached through a non-aromatic ring carbon atom). Cycloalkyl groups include groups having 3 to 10 ring atoms. Representative cycloalkyls include, but are not limited to, cycloalkyls having 3 to 10 carbon atoms, 3 to 8 carbon atoms, 3 to 6 carbon atoms, or 3 to 5 carbon atoms. Monocyclic cycloalkyl radicals include, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl. In some embodiments, the monocyclic cycloalkyl is cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl. In some embodiments, the monocyclic cycloalkyl is cyclopentyl. Polycyclic radicals include, for example, adamantyl, norbornyl, decalinyl, and 3,4-dihydronaphthalen-1(2H)-one.Unless stated otherwise in the specification, a cycloalkyl group can be optionally substituted.

[0360] "Fluoroalkyl" refers to an alkyl in which one or more hydrogen atoms are replaced by fluorine atoms. In one aspect, a fluoroalkyl is 1 -C 6 In some embodiments, fluoroalkyl is selected from trifluoromethyl, difluoromethyl, fluoromethyl, 2,2,2-trifluoroethyl, 1-fluoromethyl-2-fluoroethyl, and the like.

[0361] "Fused" refers to any ring structure described herein that is fused to an existing ring structure. When the fused ring is a heterocyclyl ring or a heteroaryl ring, any carbon atom on the existing ring structure that becomes part of the fused heterocyclyl ring or fused heteroaryl ring can be replaced with a nitrogen atom.

[0362] "Halo" or "halogen" refers to bromo, chloro, fluoro, or iodo.

[0363] "Haloalkyl" refers to an alkyl radical, as defined above, substituted by one or more halo radicals, as defined above, such as trifluoromethyl, difluoromethyl, fluoromethyl, trichloromethyl, 2,2,2-trifluoroethyl, 1,2-difluoroethyl, 3-bromo-2-fluoropropyl, 1,2-dibromoethyl, etc. Unless stated otherwise in the specification, a haloalkyl group can be optionally substituted.

[0364] "Haloalkoxy" refers to an alkoxy radical, as defined above, substituted by one or more halo radicals, as defined above, such as trifluoromethoxy, difluoromethoxy, fluoromethoxy, trichloromethoxy, 2,2,2-trifluoroethoxy, 1,2-difluoroethoxy, 3-bromo-2-fluoropropoxy, 1,2-dibromoethoxy, etc. Unless stated otherwise in the specification, a haloalkoxy group can be optionally substituted.

[0365] "Heterocycloalkyl" or "heterocyclyl" or "heterocyclic ring" refers to a stable 3- to 14-membered non-aromatic ring radical containing 2 to 10 carbon atoms and 1 to 4 heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur. Unless stated otherwise in the specification, a heterocycloalkyl radical can be a monocyclic or bicyclic ring system, which can include fused ring systems (when fused with an aryl or heteroaryl ring, the heterocycloalkyl is attached through a non-aromatic ring atom) or bridged ring systems. The nitrogen, carbon, or sulfur atoms in a heterocyclyl radical can be optionally oxidized. The nitrogen atom can be optionally quaternized. The heterocycloalkyl radical is partially or fully saturated. Examples of such heterocycloalkyl radicals include, but are not limited to, dioxolanyl, thienyl[1,3]dithianyl, decahydroisoquinolyl, imidazolinyl, imidazolidinyl, isothiazolidinyl, isoxazolidinyl, morpholinyl, octahydroindolyl, octahydroisoindolyl, 2-oxopiperazinyl, 2-oxopiperidinyl, 2-oxopyrrolidinyl, oxazolidinyl, piperidinyl, piperazinyl, 4-piperidonyl, pyrrolidinyl, pyrazolidinyl, quinuclidinyl, thiazolidinyl, tetrahydrofuryl, trithianyl, tetrahydropyranyl, thiomorpholinyl, thiamorpholinyl, 1-oxo-thiomorpholinyl, 1,1-dioxo-thiomorpholinyl. The term heterocycloalkyl also includes all ring forms of carbohydrates, including, but not limited to, monosaccharides, disaccharides, and oligosaccharides. Unless otherwise specified, a heterocycloalkyl has 2-10 carbons in the ring. In some embodiments, a heterocycloalkyl has 2-8 carbons in the ring. In some embodiments, a heterocycloalkyl has 2-8 carbons and 1 or 2 N atoms in the ring. In some embodiments, a heterocycloalkyl has 2-10 carbons, 0-2 N atoms, 0-2 O atoms, and 0-1 S atoms in the ring. In some embodiments, a heterocycloalkyl has 2-10 carbons, 1-2 N atoms, 0-1 O atoms, and 0-1 S atoms in the ring.When referring to the number of carbon atoms in a heterocycloalkyl, it is understood that the number of carbon atoms in the heterocycloalkyl is not the same as the total number of atoms (including heteroatoms) that make up the heterocycloalkyl (i.e., the skeletal atoms of the heterocycloalkyl ring). Unless stated otherwise in the specification, a heterocycloalkyl group can be optionally substituted.

[0366] "Heteroaryl" refers to an aryl group containing one or more ring heteroatoms selected from nitrogen, oxygen, and sulfur. Heteroaryl is monocyclic or bicyclic. Illustrative examples of monocyclic heteroaryl include pyridinyl, imidazolyl, pyrimidinyl, pyrazolyl, triazolyl, pyrazinyl, tetrazolyl, furyl, thienyl, isoxazolyl, thiazolyl, oxazolyl, isothiazolyl, pyrrolyl, pyridazinyl, triazinyl, oxadiazolyl, thiadiazolyl, furazanyl, indolizine, indole, benzofuran, benzothiophene, indazole, benzimidazole, purine, quinolizine, quinoline, isoquinoline, cinnoline, phthalazine, quinazoline, quinoxaline, 1,8-naphthyridine, and pteridine. Illustrative examples of monocyclic heteroaryls include pyridinyl, imidazolyl, pyrimidinyl, pyrazolyl, triazolyl, pyrazinyl, tetrazolyl, furyl, thienyl, isoxazolyl, thiazolyl, oxazolyl, isothiazolyl, pyrrolyl, pyridazinyl, triazinyl, oxadiazolyl, thiadiazolyl, and furazanyl. Illustrative examples of bicyclic heteroaryls include indolizine, indole, benzofuran, benzothiophene, indazole, benzimidazole, purine, quinolizine, quinoline, isoquinoline, cinnoline, phthalazine, quinazoline, quinoxaline, 1,8-naphthyridine, and pteridine. In some embodiments, the heteroaryl is pyridinyl, pyrazinyl, pyrimidinyl, thiazolyl, thienyl, thiadiazolyl, or furyl. In some embodiments, the heteroaryl contains 0-4 N atoms in the ring. In some embodiments, the heteroaryl contains 1-4 N atoms in the ring. In some embodiments, the heteroaryl contains 0-4 N atoms, 0-1 O atoms, and 0-1 S atoms in the ring. In some embodiments, the heteroaryl contains 1-4 N atoms, 0-1 O atoms, and 0-1 S atoms in the ring. In some embodiments, the heteroaryl is a C1-C9 heteroaryl. In some embodiments, the monocyclic heteroaryl is a C1-C5 heteroaryl.In some embodiments, the monocyclic heteroaryl is a 5- or 6-membered heteroaryl. In some embodiments, the bicyclic heteroaryl is a C6-C9 heteroaryl.

[0367] The term “optionally substituted” or “substituted” refers to any group to which the referenced group is individually and independently selected from alkyl, haloalkyl, cycloalkyl, aryl, heteroaryl, heterocycloalkyl, —OH, alkoxy, aryloxy, alkylthio, arylthio, alkylsulfoxide, arylsulfoxide, alkylsulfone, arylsulfone, —CN, alkyne, C 1 -C 6 Alkyl alkyne, halogen, acyl, acyloxy, -CO 2 H, -CO 2 Alkyl, nitro, and amino (mono- and di-substituted amino groups (e.g., -NH 2 , -NHR, -N(R) 2 ), and protected derivatives thereof. In some embodiments, the optional substituents are independently alkyl, alkoxy, haloalkyl, cycloalkyl, halogen, -CN, -NH 2 , -NH(CH 3 ), -N(CH 3 ) 2 , -OH, -CO 2 H, and -CO 2 In some embodiments, the optional substituents are independently selected from fluoro, chloro, bromo, iodo, -CH 3 , -CH 2 CH 3 , -CF 3 , -OCH 3 , and -OCF 3In some embodiments, a substituted group is substituted with one or two of the aforementioned groups. In some embodiments, any substituent on an aliphatic carbon atom (acyclic or cyclic, saturated or unsaturated carbon atom, excluding aromatic carbon atoms) includes oxo (=O). The compounds described herein may contain one or more double bonds and thus potentially give rise to cis / trans (E / Z) isomers, as well as other conformational isomers. Unless stated to the contrary, the compounds disclosed herein include all such possible isomers, as well as mixtures of such isomers.

[0368] In some embodiments, PSB and PFPA-PSB are used interchangeably to refer to poly(sulfobetaine methacrylate-co-perfluorophenyl azide methacrylate).

[0369] Certain of the materials, compounds, compositions, and components disclosed herein can be obtained commercially or readily synthesized using techniques commonly known to those of skill in the art. For example, starting materials and reagents used in preparing the disclosed compounds and compositions are available from commercial suppliers such as Aldrich Chemical Co., Milwaukee, Wis.), Acros Organics (Morris Plains, NJ), Fisher Scientific (Pittsburgh, Pa.), or Sigma (St. Louis, Mo.), or may be readily obtained from such publications as Fieser and Fieser's Reagents for Organic Synthesis, Volumes 1-17 (John Wiley and Sons, 1991), Rodd's Chemistry of Carbon Compounds, Volumes 1-5 and Supplemental volumes (Elsevier Science Publishers, 1989), Organic Reactions, Volumes 1-40 (John Wiley and Sons, 1991), March's Advanced Organic Chemistry, (John Wiley and Sons, 4th Edition), and Larock's Comprehensive Organic Transformations (VCH Publishers, 1997). These compounds are either prepared according to procedures described in references such as (E. G., et al., J. Am. Chem. Soc., 1989) or by methods known to those skilled in the art.

[0370] Unless expressly stated otherwise, it is never intended that any method described herein be construed as requiring its steps to be performed in a particular order. Thus, where a method claim does not in fact recite an order that its steps should follow, or where the claim or description does not specifically state that the steps are to be limited to a particular order, no order is ever intended to be inferred in any respect. This holds true against any possible implicit grounds of interpretation, including questions of logic regarding the placement of steps or flow of operations, obvious meanings derived from grammatical organization or punctuation, and the number or type of embodiments described herein. EXAMPLES

[0371] The following examples are provided for illustrative purposes only and are intended to be merely illustrative of the present disclosure and are not intended to limit the scope of the claims provided herein. Efforts have been made to ensure accuracy with respect to numbers (e.g., amounts, temperatures, etc.), but some error and deviation should be accounted for.

[0372] material α-Bromoisobutyryl bromide, N-Boc-ethanolamine, trifluoroacetic acid, 1,1,4,7,10,10-hexamethyltriethylenetetramine (97%), [2-(methacryloyloxy)ethyl]dimethyl-(3-sulfopropyl)ammonium hydroxide, tetrabutylammonium chloride, and copper(I) chloride are used as received from Sigma Aldrich. Sodium bicarbonate, methylene chloride, magnesium sulfate, and 2,2,2-trifluoroethanol are purchased from Alfa Aesar. Sylgard 184 kit (Dow Corning) is obtained from Fisher Chemical.

[0373] A zwitterionic polymer, polysulfobetaine (PSB), is chosen as the antifouling component of the coating. By electrostatically adsorbing water, the PSB coating forms a thin hydration barrier that prevents organic materials from adhering to its surface. Commonly used approaches to attach PSB coatings to surfaces, such as radical-initiated graft polymerization of PSB-methacrylate, require the use of oxygen-free conditions that do not meet scalability requirements, preconditioning steps, or long reaction times. To avoid the use of air-free graft polymerization, perfluorophenyl azide (PFPA) is used as a molecular anchor to graft PSB coatings to the surfaces of polymeric materials under ambient conditions. When induced with UV light, the PFPA moiety generates highly reactive nitrenes that form covalent bonds with materials containing amines, C=C double bonds, and C-H bonds. In this method, it is surprisingly found that PSB is rapidly coated onto a variety of substrates using UV light under ambient conditions without the need for a preconditioning step. In addition, it is unexpectedly found that water provides an optimal solvent for photografting of PFPA-PSB coatings, and photografting of PFPA-PSB does not proceed well in the presence of organic solvents.

[0374] Example 1. Synthesis of ATRP initiator 2-aminoethyl 2-bromoisobutyrate The ATRP initiator 2-aminoethyl 2-bromoisobutyrate is synthesized according to the following procedure. 5 g of 2-bromoisobutyryl bromide is added to a solution of 3.8 g of t-Boc-aminoethyl alcohol and 2.5 g of triethylamine in 12 ml of methylene chloride in an ice bath. After 16 hours, the salts are filtered off and the filtrate is extracted with saturated sodium bicarbonate solution. The methylene chloride phase is dried over magnesium sulfate and evaporated. The resulting t-Boc-aminoethyl 2-bromoisobutyrate is treated with 15 mL of trifluoroacetic acid (TFA) for 2 hours and crystallizes upon the addition of ethyl ether.

[0375] Example 2. Synthesis of PFPAS-methacrylate / acrylate [ka] 2-Aminoethyl methacrylate / acrylate hydrochloride is dissolved in DI water at a concentration of 0.56M. Two equivalents of sodium bicarbonate are added dropwise to the solution. In a separate vial, one equivalent of pentafluorobenzenesulfonyl chloride is dissolved in acetone at a concentration of 0.186M. Both solutions are cooled to 4°C. The solution containing 2-aminoethyl methacrylate / acrylate and sodium bicarbonate is added dropwise to the pentafluorobenzenesulfonyl chloride solution on ice. The reaction is stirred and allowed to warm gradually to room temperature. After 3 hours, 3 equivalents of sodium azide are added to the solution and the reaction is allowed to stir at room temperature for an additional 18 hours. The acetone is then removed under reduced pressure. Three times the reaction volume of methyl tert-butyl ether is added to the crude mixture and poured into a separatory funnel. DI water is added three times to wash the organic layer. The methyl tert-butyl ether is removed under reduced pressure to give the desired product.

[0376] Example 3. Synthesis of PFPAA-methacrylate / methacrylamide / acrylate / acrylamide [ka] 4-Azidotetrafluorobenzoic acid was prepared according to the published procedure by Keana et al. (J. Org. Chem. 1990, 55(11), 3640-7). To prepare PFPAA-methacrylate, N-3-aminopropyl methacrylate hydrochloride and triethylamine are dissolved in dichloromethane to a concentration of 0.31 M each. This solution is stirred for 3 hours. 4-Azidotetrafluorobenzoic acid is then dissolved to a concentration of 0.235 M. 4-Dimethylaminopyridine is then added to the solution containing 4-Azidotetrafluorobenzoic acid (0.26 M). A second portion of triethylamine is added so that the final concentration of triethylamine in the reaction is 0.56 M. The reaction is then stirred for 48 hours, washed three times with DI water, and the organic layer is evaporated under reduced pressure to give the desired product. This procedure is used to prepare different PFPA amide-methacrylate / methacrylamide / acrylate / acrylamide compounds.

[0377] Example 4. Synthesis of PFPAE-methacrylate / methacrylamide / acrylate / acrylamide [ka] 4-Azidotetrafluorobenzoic acid was prepared according to the published procedure by Keana et al. (J. Org. Chem. 1990, 55(11), 3640-7). To prepare PFPAE-methacrylamide, 2-hydroxyethylmethacrylamide and triethylamine are dissolved in dichloromethane to a concentration of 0.31 M each. This solution is stirred for 3 hours. 4-Azidotetrafluorobenzoic acid is then dissolved to a concentration of 0.235 M. 4-Dimethylaminopyridine is then added to the solution containing 4-Azidotetrafluorobenzoic acid (0.26 M). A second portion of triethylamine is added so that the final concentration of triethylamine in the reaction is 0.56 M. The reaction is then stirred for 48 hours, washed three times with DI water, and the organic layer was evaporated under reduced pressure to give the desired product. This procedure is used to prepare different PFPA ester-methacrylate / methacrylamide / acrylate / acrylamide compounds.

[0378] Example 5. Polymerization of sulfobetaine methacrylate and perfluorophenyl azide to form a copolymer [ka] The copolymers are synthesized as follows: 2 g of sulfobetaine methacrylate monomer 5-1, 100 mg, 150 mg, or 200 mg of perfluorophenyl azide monomer 5-2, and 2 g of tetrabutylammonium chloride are dissolved in 30 mL of trifluoroethanol in a Schlenk tube and subjected to two vacuum-argon cycles. Then, 14 mg of Cu(I)Cl and 76 μL of 1,1,4,7,10,10-hexamethyltriethylenetetramine are added. The Schlenk tube is sealed with a rubber septum and subjected to two more vacuum-argon cycles. Finally, 44 mg of TFA-protected 2-aminoethyl 2-bromoisobutyrate as an ATRP initiator is dissolved in a small amount of trifluoroethanol (approximately 0.5 mL) and injected with a syringe into the Schlenk tube, followed by two more vacuum-argon cycles. Polymerization is carried out at 60 °C under argon. After 24 hours, the reaction mixture is cooled to room temperature and the copolymer is purified by performing membrane dialysis using a membrane with a molecular weight cut-off of 1000 Daltons. The copolymer obtained is lyophilized before further use.

[0379] NMR spectra are recorded on a Bruker DPX300 spectrometer. Chemical shifts are calibrated to the residual solvent signal. Molecular weights and dispersities are measured by gel permeation chromatography on a Shimadzu HPLC system equipped with a refractive index detector S3 RID-10A, one Tosoh TSKGel guard column, and one Tosoh TSKGel G4000PW column. The eluent was 0.1 M NaNO at 25 °C. 3 +20 mM phosphate buffer (pH 7 + 20% MeCN) (flow rate 0.7 mL / min). Calibration is performed using near monodisperse PEG standards from Polymer Laboratories. Light scattering is used to obtain absolute molecular weights.

[0380] Example 6. Synthesis of mixed-charged copolymers [ka] Monomers 6-2, 6-3, and 6-4 are dissolved in different molar ratios in a solution of 4:1 TFE:DMF at a total concentration of 0.37M. 6-1 is added at a concentration of 0.022M, and the radical initiator (AIBN) is added at a concentration of 0.0037M. The reaction is carried out protected under argon gas using common Schlenk line techniques. Oxygen is removed under reduced pressure and filled with argon gas three times. The reaction is stirred with a mechanical stir bar and heated to 60°C using an oil bath. After 72 hours, the reaction solvent is removed under reduced pressure using a rotary evaporator to ¼ of the original reaction volume. Once concentrated, the polymer crude mixture is diluted with DI water by 10 times its volume. Residual monomers and oligomers are removed by pipetting the crude polymer reaction mixture into a cellulose dialysis bag with a molecular weight cutoff of 10,000 Daltons and placing the filled dialysis bag in a large water bath. The water bath is replenished with fresh deionized water for 7 consecutive days. The purified polymer solution dispersed in water in a dialysis bag is lyophilized to remove the water and obtain a white powder. The molar ratios of 6-2, 6-3, and 6-4 can be varied to synthesize mixed-charged copolymers of different isoelectric points.

[0381] Example 7. Synthesis of mixed-charged copolymers [ka] Monomers 6-3 and 6-4 are dissolved in different molar ratios in a solution of 4:1 TFE:DMF at a total concentration of 0.37M. 6-1 is added at a concentration of 0.022M and the radical initiator (AIBN) is added at a concentration of 0.0037M. The reaction is carried out protected under argon gas using common Schlenk line techniques. Oxygen is removed under reduced pressure and filled with argon gas three times. The reaction is stirred with a mechanical stir bar and heated to 60°C using an oil bath. After 72 hours, the reaction solvent is removed under reduced pressure using a rotary evaporator to ¼ of the original reaction volume. Once concentrated, the polymer crude mixture is diluted with DI water by 10 times its volume. Residual monomers and oligomers are removed by pipetting the crude polymer reaction mixture into a cellulose dialysis bag with a molecular weight cutoff of 10,000 Daltons and placing the filled dialysis bag in a large water bath. The water bath is replenished with fresh deionized water for 7 consecutive days. The purified polymer solution dispersed in water in a dialysis bag is lyophilized to remove the water and obtain a white powder. The molar ratio of 6-3 and 6-4 can be altered to synthesize mixed-charged copolymers of different isoelectric points.

[0382] Example 8. Synthesis of PFPA positively and PFPA negatively charged copolymers It is hypothesized that a surface with a 1:1 molar ratio of positive and negative moieties will have superior anti-fouling properties. To achieve a 1:1 molar ratio of positive and negative moieties on a surface, two separate copolymers can be polymerized, each containing either positively or negatively charged moieties, and then blended together in a 1:1 molar ratio in solution. An example of this is shown below. [ka]

[0383] To synthesize the negatively charged PFPA-sulfonic acid copolymer, monomer 6-3 is dissolved in a solution of 4:1 TFE:DMF at a concentration of 0.37M. 6-1 is added at a concentration of 0.022M, and a radical initiator (AIBN) is added at a concentration of 0.0037M. The reaction is carried out under protection of argon gas using common Schlenk line techniques. Oxygen is removed under reduced pressure and filled with argon gas three times. The reaction is stirred with a mechanical stir bar and heated to 60°C using an oil bath. After 72 hours, the reaction solvent is removed under reduced pressure using a rotary evaporator to ¼ of the original reaction volume. Once concentrated, the polymer crude mixture is diluted with deionized water by 10 times its volume. Residual monomers and oligomers are removed by pipetting the crude polymer reaction mixture into a cellulose dialysis bag with a molecular weight cutoff of 10,000 Daltons and placing the filled dialysis bag in a large water bath. The water bath is replenished with fresh deionized water for 7 consecutive days. The purified polymer solution dispersed in water in a dialysis bag is freeze-dried to remove the water and obtain a white powder. [ka]

[0384] To synthesize the positively charged PFPA-quaternary ammonium copolymer, monomer 6-4 is dissolved in a solution of 4:1 TFE:DMF at a concentration of 0.37M. 6-1 is added at a concentration of 0.022M, and a radical initiator (AIBN) is added at a concentration of 0.0037M. The reaction is carried out under protection of argon gas using common Schlenk line techniques. Oxygen is removed under reduced pressure and filled with argon gas three times. The reaction is stirred with a mechanical stir bar and heated to 60°C using an oil bath. After 72 hours, the reaction solvent is removed under reduced pressure using a rotary evaporator to ¼ of the original reaction volume. Once concentrated, the polymer crude mixture is diluted with deionized water by 10 times its volume. Residual monomers and oligomers are removed by pipetting the crude polymer reaction mixture into a cellulose dialysis bag with a molecular weight cutoff of 10,000 Daltons and placing the filled dialysis bag in a large water bath. The water bath is replenished with fresh deionized water for 7 consecutive days. The purified polymer solution dispersed in water in a dialysis bag is freeze-dried to remove the water and obtain a white powder.

[0385] Once the powders of the positively charged copolymer and the negatively charged copolymer are obtained, they are each dissolved in a suitable solvent (H 2 2,3,4-Trifluoroethanol (DMF, 2,2,2-trifluoroethanol, DMSO, DMAc, etc.) to create a 1:1 molar ratio of sulfonic acid moieties and quaternary ammonium moieties. The resulting mixture is used to modify the surface.

[0386] Example 9. UV light silicone surface modification and characterization The copolymers of Examples 5 or 6 are dissolved or suspended in DI water to prepare 2-20 mg / mL aqueous mixtures. Silicone elastomer films are prepared by mixing 10:1 (by weight) base:crosslinker (Sylgard 184), followed by degassing under vacuum and then crosslinking at 70°C for 8 hours. For biofouling resistance experiments, 2 mg / mL of the copolymer aqueous mixture is spread on the cured silicone elastomer surface and exposed to 254 nm UV light irradiation for 10 minutes. The silicone elastomer surface is then rinsed with copious amounts of DI water to remove unreacted and physically adsorbed copolymer molecules from the surface and stored under water layer before further use.

[0387] The contact angle of deionized water (18 MΩ / cm, Millipore) on the polymer coating is measured using a Rame-Hart Model 590 goniometer. The advancing angle (θ ADV ) is measured, while the receding angle (θ REC ) is measured. The total drop volume is about 5 μL and the pump dispense rate is about 0.2 μL / sec. Measurements are taken at three or more different locations on each surface and values ​​reported are in the form of mean ± standard deviation.

[0388] For surface modification, the following photoreaction takes place: 2 PFPA decomposes by releasing phenylnitrene to obtain singlet phenylnitrene upon activation of the compound by UV light. Singlet phenylnitrene further undergoes CH or NH insertion and C=C addition reactions that contribute to covalent bond formation with the target surface (Liu, L.-H. et al. Perfluorophenyl azides: new applications in surface functionalization and nanomaterial synthesis. Accounts of Chemical Research 2010,43(11),1434-1443). In this process, the "singlet phenylnitrene" reaction intermediate is a strong nucleophile and its stability is not affected by the presence of oxygen and water molecules.

[0389] Example 10. Silicone surface thermal modification and characterization Four 2 cm segments of catheters (16fr) were immersed in a solution of 10 mg / mL PFPA-PSB copolymer dissolved in DI water in a sealed flask and subjected to a 1 hour heating period at various temperatures (80° C., 100° C., 120° C., 140° C., 160° C., 180° C., 200° C., or 220° C.). The catheter segments were then removed from the solution and rinsed by slowly immersing twice in fresh DI water and blotted with paper towels to remove liquid from the lumen of the samples. The catheters were then allowed to dry.

[0390] A dye solution of 3 mg / mL crystal violet-HCl solution in DI water was stirred overnight. The modified catheter segments and a similar set of unmodified catheter segments were individually immersed in the crystal violet solution for 1 minute, then rinsed by immersing twice in fresh DI water and blotting with a paper towel to remove liquid from the lumen of the samples. The catheter segments were then placed in scintillation vials.

[0391] 10 mL of 2:1 DI water:acetic acid was added to each vial. Each vial was shaken vigorously for 30 seconds to remove any adsorbed crystal violet from the catheters. 2 mL of solution was removed from each tube and placed in a cuvette and the absorbance was measured at 580 nm. Each solution was diluted 2-fold because the initial readings were too high. The absorbance measurements at 580 nm of unmodified (control) and modified catheters with heat treatment at different temperatures are listed in Table E-10 below. [Table 1]

[0392] Example 11. Substrate modification and characterization Coat the substrate with PSB: Prepare the PDMS substrate by mixing elastomer to curing agent in a 10:1 ratio, followed by curing at 80 °C for 1 h. Cut the PDMS disks into 3 mm diameter disks with a laser cutter. Approximately 2, 5, or 10 mg mL -1 30 μL of the coating (PSB) mixture having a concentration of is placed and spread on the surface of each disk. The PSB is then crosslinked onto the disk by exposure to 254 nm UV light for 10 minutes under sterile conditions, followed by rinsing with Milli-Q water and air drying.

[0393] Visualization and measurement of contact angles: Water contact angles of various substrates such as PDMS, nylon 66, polystyrene, polyvinyl chloride, and polyethylene are visualized by placing 17 μL of Milli-Q water on the flat substrates at room temperature and subsequently imaging them. Fta32 version 2.1 software is used to analyze the images and measure the contact angles. To study the recovery of water contact angles of PDMS substrates, they are divided into two groups: (i) O 2 The PDMS sheets were divided into (i) uncoated PDMS sheets, which were treated with plasma (Plasma Etch PE25-JW Plasma Cleaner, NV, US) for 1 min, followed by measurement of the water contact angle after 1, 2, 4, 7, and 10 days, and (ii) PDMS sheets, which were coated with PSB, and similarly the contact angle was measured over time.

[0394] XPS studies are performed on a Kratos AXIS Ultra DLD with a monochromatic Al Kα X-ray source operating at 10 mA and 15 kV. Survey spectra and individual high-resolution spectra are collected using pass energies of 160 and 20 eV, respectively. Data processing is performed using CasaXPS 2.3 software to calibrate the spectral binding energies by assigning the hydrocarbon peak of the C1s high-resolution spectrum to 284.6 eV.

[0395] Cell culture: NIH / 3T3 fibroblasts are cultured in cell culture flasks containing DMEM with 10% FBS and 1% P / S and passaged twice a week. For this purpose, a standard cell culture incubator (Thermo Fisher Scientific, PA, USA) is used, maintained at 5% CO 2 Provide atmosphere and temperature = 37° C. To perform cell studies, trypsinize fibroblasts using 0.5% trypsin-EDTA, count them using a hemocytometer, and subsequently seed them onto the desired substrate.

[0396] Cell attachment: Trypsinized fibroblasts were plated onto treated well plates with 100 µL of cell suspension (approximately 1 × 10 cells in 1 mL of medium). 5 The cells are seeded into PSB-coated 96-well plates by plating 100 μl of cells at a cell density of 1000 μg / ml each (cell density of 1000 μg / ml) and cultured for 24 h. An uncoated well plate is used as a control.

[0397] Cytotoxicity assessment: To assess the cytotoxicity of uncrosslinked PSB, trypsinized fibroblasts were cultured in 100 µL of cell suspension (approximately 1 × 10 in 1 mL of medium). 5 The cells were seeded into 96-well plates by placing 500 µL of cell suspension (approximately 2 × 10 cells in 1 mL of medium) in a 24-well plate and incubated for 24 h, followed by adding a desired amount of non-crosslinked PSB to the medium and culturing for an additional 72 h. The cytotoxicity of crosslinked PSB was evaluated by adding 500 µL of cell suspension (approximately 2 × 10 cells in 1 mL of medium) to a 24-well plate. 5 The cells are seeded at a cell density of 1000 x 1000 mm and cultured for 24 hours, followed by placing a PSB-coated PDMS disk (approximately 6 mm in diameter and 3 mm in height) in the medium and culturing for an additional 72 hours.

[0398] Metabolic activity assessment: MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) (Thermo Fisher Scientific) staining solution was diluted to approximately 5 mg mL in DPBS. -1The cell culture medium is removed from the well plate, followed by rinsing once with DPBS. The wells are then filled with fresh medium and MTT solution in a 9:1 ratio. The well plate is wrapped in aluminum foil and stored at 37°C and 5% CO. 2 After 4 hours, the wells are aspirated with a pipette and 200 or 500 μL of DMSO is added to the 96- and 24-well plates, respectively. The well plates are wrapped in aluminum foil again and placed on a rotator for 30 minutes, after which the absorbance is recorded at 570 nm using a microplate reader (Synergy HTX multimode reader, BioTek, VT, USA).

[0399] Live / Dead Assay: A Live / Dead fluorescent assay is used to assess cell viability. The staining solution is prepared by adding ethidium homodimer-1 (20 μL) and calcein AM (5 μL) to DPBS (10 mL). To perform the assay, cells are incubated with 1 mL of staining solution for approximately 20 min and imaged using a fluorescence microscope (Axio Observer 5, Zeiss, Germany) at excitation / emission wavelengths of approximately 494 / 515 nm for calcein and 528 / 617 nm for ethidium homodimer-1.

[0400] Protein adsorption: Protein adsorption is 50 μg mL of 100 μg -1The fluorescence intensity of BSA conjugated with Alexa Fluor™ 488 (AF) is evaluated on each PDMS substrate by incubating it for 1 hour at 37°C. Aluminum foil is used to wrap the substrate to inhibit photodegradation of AF. The PDMS substrate is then gently rinsed with Milli-Q water and imaged using a fluorescence microscope (Axio Observer 5, Zeiss, Germany) at excitation / emission wavelengths of approximately 488 / 517 nm with a constant exposure time of approximately 1.13 ms. ImageJ (National Institutes of Health, US) is used to quantify the emitted fluorescence by the mean gray value analysis tool. The mean pixel brightness indirectly reflects the amount of protein adsorbed to the substrate. AF-free samples are used as controls to exclude background autofluorescence.

[0401] Bacterial Culture: The bacterial species E. coli, S. epidermidis, S. aureus Rosenbach, S. aureus (MRSA), P. aeruginosa, and C. albicans are used in this work. All strains are incubated at 30°C at 150 rpm until they reach mid-log phase, at which point the cells are harvested by centrifugation at 3800xg for 8 minutes. E. coli is grown on Luria-Bertani (LB) broth, S. epidermidis, P. aeruginosa, and S. aureus Rosenbach are grown on nutrient broth, S. aureus (MRSA) is grown on trypticase soy broth (TSB), and C. albicans is grown on yeast mold (YM) broth. These initial cultures are then adjusted to an optical density of 1 at 600 nm and 1 x 10 per mL. 7 Cells ~ 1 x 10 per mL 8 The initial total cell numbers ranged from 100 to 200 cells.

[0402] Bacterial attachment: 55 mm diameter Petri dishes are filled with 10:1 elastomer to curing agent (Sylgard 184) and cured at room temperature for at least 48 h to form a 3 mm thick PDMS film on the bottom of the dish. The modified plates are coated with a solution containing PFPA-PSB and irradiated with 254 nm UV light. Each of the modified and unmodified PDMS-lined dishes is seeded with 4 mL of bacterial or fungal suspension and incubated at 35 °C for 24-72 h (shaking at 25 rpm). The bacterial or fungal suspension is then removed and stored for further microscopic examination. The Petri dishes are gently rinsed with sterile deionized water using a Pasteur pipette and covered with 4 mL of dye solution (SYTO 9 live / dead Baclight Bacterial Viability Kit L13152, Molecular Probes) for 15 min. SYTO 9 solution is prepared by dissolving the contents of component A of the kit in 30 mL of sterile deionized water. After staining is completed, the Petri dishes are gently rinsed with deionized water and imaged using a 4x CCD camera (Axiocam MRm System) mounted on a Zeiss Axioskop 2 microscope equipped with a 10x objective, a 40x objective, a fluorescent lamp, and a blue excitation filter. During observation, images are taken with an excitation range of 450-490 nm. The number of attached microorganisms on all fluorescent images is determined using ImageJ software.

[0403] Statistical analysis: Data are reported as the mean ± standard deviation of at least triplicate experiments. One-way analysis of variance (ANOVA) and Tukey's multiple comparisons were used to identify statistically significant differences for p-values ​​less than 0.05 (*p<0.05), 0.01 (**p<0.01), 0.001 (***p<0.001), and 0.0001 (****p<0.0001).

[0404] Escherichia coli is used as a model bacterium for this study. Pure bacterial cell cultures are suspended in Luria-Bertani (LB) broth and grown at 35°C with shaking at 150 rpm until they reach mid-log phase, at which point the cells are harvested by centrifugation at 3800 x g for 8 minutes. The cells are then diluted with fresh LB medium at 4 x 10 7 Resuspend to a concentration of 100 cells / mL. 2 Membrane coupons are incubated in this bacterial suspension for 24 hours at 25 rpm and 35°C. The coupons are then removed from the suspension and rinsed gently with fresh LB broth using a Pasteur pipette. Once rinsed, the coupons are immersed in dye solution (SYTO 9 live / dead Baclight Bacterial Viability Kit L13152, Molecular Probes) for 15 minutes. SYTO 9 solution is prepared by dissolving the contents of component A of the kit in 30 mL of sterile distilled water. After staining is complete, the coupons are gently rinsed with fresh LB broth and imaged using a microscope (Olympus BX51 microscope) equipped with a fluorescent light and green / red fluorescent filters, and a 4x CCD camera attachment (FVIEW-II, Soft Imaging System, USA).

[0405] Although preferred embodiments of the present disclosure have been shown and described herein, it will be apparent to those skilled in the art that such embodiments are provided by way of example only. Numerous variations, changes, and substitutions will occur to those skilled in the art without departing from the present disclosure. It should be understood that various alternatives to the embodiments of the present disclosure described herein can be used in the practice of the present disclosure. The following claims define the scope of the present disclosure, and it is intended that methods and structures within the scope of these claims and their equivalents be covered thereby.

[0406] Numbered Embodiments Embodiment 1 is a compound having the structure of formula (I): [ka] During the ceremony, A is -C(=O)-, -S(=O)-, -S(=O) 2 - and -S(=O)(-NR 3 )- is selected from L is -OQ, -NR 3 Q, and -N(R 3 ) 2 Q + is selected from Q is a structure represented by the following formula: [ka] Z is -CR 6a R 6b -, -C(=O)-, -C(=NH)-, and -C(=NH)NR 7 - selected from m is an integer selected from 0, 1, 2, 3, 4, 5, 6, 7, and 8; Each R 1a and R 1b is independently selected from hydrogen and halogen; Each R 2a and R 2b are independently selected from halogen, -CN, and optionally substituted C 1 -C 6 fluoroalkyl; Each R 3 are independently hydrogen, optionally substituted C 1 -C 4 Alkyl, -X-optionally substituted C 1 -C 4 selected from alkyl, optionally substituted aryl, and -X-optionally substituted aryl; X is -C(=O)-, -S(=O)-, or -S(=O) 2 - and Each R 4a , R 4b , R 5a , R 5c , R 6a , and R 6bare independently hydrogen, halogen, -CN, -OH, optionally substituted C 1 -C 4 Alkyl, optionally substituted C 1 -C 4 Fluoroalkyl, optionally substituted aryl, -NR 8a R 8b , -NR 8a R 8b R 8c+ , -S(=O) 2 O - , -S(=O) 2 OR 9 , -C(=O)O - , and -C(=O)OR 9 is selected from R 5b -OR 10b , -NR 10a R 10b , or -NR 10a R 10b R 10c+ and Each R 7 , R 8a , R 8b , R 8c , and R 9 are independently hydrogen and optionally substituted C 1 -C 4 selected from alkyl and optionally substituted aryl; Each R 10a and R 10c are independently hydrogen, optionally substituted C 1 -C 4 Alkyl, optionally substituted aryl, -(optionally substituted C 1 -C 8 Alkylene)S(=O) 2 O - , -(optionally substituted C 1 -C 8 Alkylene)S(=O) 2 OH, -(optionally substituted C 1 -C 8 Alkylene)C(=O)O - , and -(optionally substituted C 1 -C8 alkylene)C(=O)OH; R 10b is -C(=O)-C 2 -C 6 Alkenyl, -S(=O)-C 2 -C 6 Alkenyl, or -S(=O) 2 -C 2 -C 6 Although it is alkenyl, With the proviso that the compound of formula (I) is N-(2-((4-azido-2,3,5,6-tetrafluorophenyl)sulfonamido)ethyl)methacrylamide, N-(2-acrylamidoethyl)-4-azido-2,3,5,6-tetrafluorobenzamide, or Not 2-(methacryloyloxy)ethyl 4-azido-2,3,5,6-tetrafluorobenzoate.

[0407] Embodiment 2 is a compound according to embodiment 1, wherein the compound is [ka] The structure is selected from:

[0408] Embodiment 3 is a compound according to embodiment 1 or 2, wherein the compound is [ka] The structure is selected from:

[0409] Embodiment 4 is a compound according to any one of embodiments 1 to 3, wherein the compound is [ka] The structure is selected from:

[0410] Embodiment 5 is a compound according to embodiment 1, wherein the compound is [ka] The structure is selected from:

[0411] Embodiment 6 is a compound described in embodiment 1, wherein the compound has the structure: [ka] .

[0412] Embodiment 7 is a compound according to embodiment 5 or 6, wherein R 1a , R 1b , R 2a , and R 2b are each -F.

[0413] Embodiment 8 is a compound according to any one of embodiments 1 to 7, wherein Z is -CR 6a R 6b -It is.

[0414] Embodiment 9 is a compound according to embodiment 8, wherein R 6a and R 6b are each hydrogen.

[0415] Embodiment 10 is a compound of any one of embodiments 1-9, wherein m is 0, 1, 2, or 3.

[0416] Embodiment 11 is a compound of embodiment 10, wherein m is 0.

[0417] Embodiment 12 is a compound according to any one of embodiments 1 to 11, wherein R 5a is hydrogen and R 5b -NR 10a R 10b and R 5c is hydrogen.

[0418] Embodiment 13 is a compound according to any one of embodiments 1 to 11, wherein R 5a is hydrogen and R 5b -OR 10b and R 5c is hydrogen.

[0419] Embodiment 14 is a compound according to embodiment 1, wherein the compound has formula (Ia): [ka] It has the structure:

[0420] Embodiment 15 is a compound according to embodiment 1, wherein the compound has formula (Ib): [ka] It has the structure:

[0421] Embodiment 16 is a compound according to embodiment 1, wherein the compound of formula (I) has formula (Ic): [ka] It has the structure:

[0422] Embodiment 17 is a compound according to embodiment 1, wherein the compound of formula (I) has the formula (Id): [ka] It has the structure:

[0423] Embodiment 18 is a compound according to any one of embodiments 1 to 17, wherein R 10a is hydrogen.

[0424] Embodiment 19 is a compound according to embodiment 1, wherein the compound of formula (I) has formula (Ie): [ka] It has the structure:

[0425] Embodiment 20 is the compound of embodiment 1, wherein the compound of formula (I) has the formula (If): [ka] It has the structure:

[0426] Embodiment 21 is a compound according to embodiment 1, wherein the compound of formula (I) has formula (Ig): [ka] It has the structure:

[0427] Embodiment 22 is the compound of embodiment 1, wherein the compound of formula (I) has formula (Ih): [ka] It has the structure:

[0428] Embodiment 23 is a compound according to any one of embodiments 1 to 15, 19, or 20, wherein R 3 is hydrogen.

[0429] Embodiment 24 is a compound having the structure of formula (II): [ka] During the ceremony, Each R 1a and R 1b is independently selected from hydrogen and halogen; Each R 2a and R 2b is independently selected from halogen, —CN, and optionally substituted C1-C6 fluoroalkyl; Each A 1 , A 2 , and A 3 are independently -C(=O)-, -S(=O)-, -S(=O) 2 - and -S(=O)(=NR 3c )- is selected from Each B 1 , B 2 , and B. 3 are independently -O- and -NR 3c - selected from D is -S(=O)2 O - , -S(=O) 2 OR 9a , -C(=O)O - , or -C(=O)OR 9a and Z 1 is -(CR 6c R 6d ) s - and Z 2 is -(CR 6c R 6d ) t - and Z 3 is -(CR 6c R 6d ) p - and Each R 3a and R 3b are independently hydrogen, optionally substituted C 1 -C 4 alkyl, and optionally substituted benzyl; Each R 4c , R 4d , R 5d , R 5e , R 6c , and R 6d are independently hydrogen, halogen, -CN, -OH, optionally substituted C 1 -C 4 Alkyl, optionally substituted C 1 -C 4 Fluoroalkyl, optionally substituted C 2 -C 6 Alkenyl, -NR 3c R 3d , -S(=O) 2 O - , -S(=O) 2 OR 9a , -C(=O)O - , and -C(=O)OR 9a is selected from Each R 3c and R 3d are independently hydrogen, optionally substituted C 1 -C 4Alkyl, -X-optionally substituted C 1 -C 4 Alkyl, optionally substituted C 2 -C 6 alkenyl, and optionally substituted aryl; X is -C(=O)-, -S(=O)-, or -S(=O) 2 - and Each R 9a , R 11a , R 11b , R 11c , R 12a , R 12b , and R 12c are independently hydrogen, optionally substituted C 1 -C 4 alkyl, and optionally substituted aryl; n is an integer selected from 0, 1, 2, 3, 4, 5, 6, 7, and 8; s is an integer selected from 1, 2, 3, 4, or 5; t is an integer selected from 1, 2, 3, 4, or 5; p is an integer selected from 1, 2, 3, 4, or 5; x is 0.001 to 0.999, The compounds of formula (II) are charged or zwitterionic, However, the compound of formula (II) [ka] isn't it.

[0430] Embodiment 25 is a compound according to embodiment 24, wherein each R 1a and R 1b are independently halogen.

[0431] Embodiment 26 is a compound according to embodiment 24 or 25, wherein each R 1a and R 1b is independently F or Cl.

[0432] Embodiment 27 is a compound according to any one of embodiments 24 to 26, wherein R 1a and R 1b are each F.

[0433] Embodiment 28 is a compound according to any one of embodiments 24 to 27, wherein each R 2a and R 2b are independently halogen, -CN, and -CF 3 is selected from.

[0434] Embodiment 29 is a compound according to any one of embodiments 24 to 28, wherein each R 2a and R 2b are independently F, Cl, -CN, and -CF 3 is selected from.

[0435] Embodiment 30 is a compound according to any one of embodiments 24 to 29, wherein R 2a and R 2b are each F.

[0436] Embodiment 31 is a compound according to any one of embodiments 24 to 30, 1 is -S(=O) 2 - and A 2 is -C(=O)-, and A 3 is -C(=O)-.

[0437] Embodiment 32 is a compound according to any one of embodiments 24 to 31, 1 and B. 2 are respectively, -NR 3c -It is.

[0438] Embodiment 33 is a compound according to embodiment 32, wherein R 3c is hydrogen or -CH 3 It is.

[0439] Embodiment 34 is a compound according to embodiment 33, wherein R 3c is hydrogen.

[0440] Embodiment 35 is a compound according to any one of embodiments 24 to 34, wherein B 3 is -O-.

[0441] Embodiment 36 is a compound according to any one of embodiments 24 to 35, wherein D is -S(=O) 2 OR 9a OR -C(=O)OR 9a It is.

[0442] Embodiment 37 is a compound according to embodiment 36, wherein R 9a is hydrogen or -CH 3 It is.

[0443] Embodiment 38 is a compound according to any one of embodiments 24 to 35, wherein D is -S(=O) 2 O - or -C(=O)O - It is.

[0444] Embodiment 39 is a compound according to embodiment 38, wherein D is -S(=O) 2 O - It is.

[0445] Embodiment 40 is a compound according to any one of embodiments 24 to 39, wherein each R 6c and R 6d is hydrogen.

[0446] Embodiment 41 is a compound according to any one of embodiments 24 to 40, wherein each R 3a and R 3b -CH 3 It is.

[0447] Embodiment 42 is a compound according to any one of embodiments 24 to 41, wherein R 11a is hydrogen or -CH 3 It is.

[0448] Embodiment 43 is a compound according to embodiment 42, wherein R 11a -CH3 It is.

[0449] Embodiment 44 is a compound according to any one of embodiments 24 to 43, wherein R 12a is hydrogen or -CH 3 It is.

[0450] Embodiment 45 is a compound according to embodiment 44, wherein R 12a -CH 3 It is.

[0451] Embodiment 46 is a compound according to any one of embodiments 24 to 45, wherein each R 11b , R 11c , R 12b , and R 12c is hydrogen.

[0452] Embodiment 47 is a compound having the structure of formula (III): [ka] During the ceremony, Each R 1a and R 1b is independently selected from hydrogen and halogen; Each R 2a and R 2b are independently selected from halogen, -CN, and optionally substituted C 1 -C 6 fluoroalkyl; Each A 1 , A 2 , and A 3 are independently -C(=O)-, -S(=O)-, -S(=O) 2 - and -S(=O)(=NR 3c )- is selected from Each B 1 , B 2 , and B. 3 are independently -O- and -NR 3c - selected from Z 1 is -(CR 6c R 6d )s - and Z 2 is -(CR 6c R 6d ) t - and E is -CN, -OR 9a , -NR 9a R 9b , -NR 9a R 9b R 9c+ , optionally substituted C 1 -C 4 Alkyl, optionally substituted C 1 -C 6 Fluoroalkyl, -S(=O) 2 O - , -S(=O) 2 OR 9a , -C(=O)O - , or -C(=O)OR 9a and Each R 4c , R 4d , R 5d , R 5e , R 6c , and R 6d are independently hydrogen, halogen, -CN, -OR 9a , optionally substituted C 1 -C 4 Alkyl, optionally substituted C 1 -C 4 Fluoroalkyl, optionally substituted C 2 -C 6 Alkenyl, -NR 3c R 3d , -S(=O) 2 O - , -S(=O) 2 OR 9a , -C(=O)O - , and -C(=O)OR 9a is selected from Each R 3c and R 3d are independently hydrogen, optionally substituted C 1 -C 4 Alkyl, -X-optionally substituted C 1 -C 4Alkyl, optionally substituted C 2 -C 6 alkenyl, and optionally substituted aryl; X is -C(=O)-, -S(=O)-, or -S(=O) 2 - and Each R 9a , R 9b , R 9c , R 11a , R 11b , R 11c , R 12a , R 12b , and R 12c are independently hydrogen, optionally substituted C 1 -C 4 alkyl, and optionally substituted aryl; n is an integer selected from 0, 1, 2, 3, 4, 5, 6, 7, and 8; s is an integer selected from 1, 2, 3, 4, or 5; t is an integer selected from 1, 2, 3, 4, or 5; x is between 0.001 and 0.999.

[0453] Embodiment 48 is a compound according to embodiment 47, wherein each R 1a and R 1b are independently halogen.

[0454] Embodiment 49 is a compound according to embodiment 47 or 48, wherein each R 1a and R 1b is independently F or Cl.

[0455] Embodiment 50 is a compound according to any one of embodiments 47 to 49, wherein R 1a and R 1b are each F.

[0456] Embodiment 51 is a compound according to any one of embodiments 47 to 50, wherein each R 2a and R 2b are independently halogen, -CN, and -CF3 is selected from.

[0457] Embodiment 52 is a compound according to any one of embodiments 47 to 51, wherein each R 2a and R 2b are independently F, Cl, -CN, and -CF 3 is selected from.

[0458] Embodiment 53 is a compound according to any one of embodiments 47 to 52, wherein R 2a and R 2b are each F.

[0459] Embodiment 54 is a compound according to any one of embodiments 47 to 53, wherein A 1 is -S(=O) 2 - and A 2 is -C(=O)-, and A 3 is -C(=O)-.

[0460] Embodiment 55 is a compound according to any one of embodiments 47 to 54, wherein B 1 and B. 2 are respectively, -NR 3c -It is.

[0461] Embodiment 56 is a compound according to embodiment 55, wherein R 3c is hydrogen or -CH 3 It is.

[0462] Embodiment 57 is a compound according to embodiment 56, wherein R 3c is hydrogen.

[0463] Embodiment 58 is a compound according to any one of embodiments 47 to 57, wherein B 3 -NR 3c -It is.

[0464] Embodiment 59 is a compound according to embodiment 58, wherein R 3c is hydrogen.

[0465] Embodiment 60 is a compound according to any one of embodiments 47 to 59, wherein E is -NR 9a R 9b R 9c+ or -S(=O) 2 OR 9a It is.

[0466] Embodiment 61 is a compound according to embodiment 60, wherein E is -NR 9a R 9b R 9c+ It is.

[0467] Embodiment 62 is a compound according to embodiment 61, wherein each R 9a , R 9b , and R 9c is hydrogen or -CH 3 It is.

[0468] Embodiment 63 is a compound according to embodiment 62, wherein each R 9a , R 9b , and R 9c is hydrogen.

[0469] Embodiment 64 is a compound according to embodiment 62, wherein each R 9a , R 9b , and R 9c -CH 3 It is.

[0470] Embodiment 65 is a compound according to embodiment 60, wherein E is -S(=O) 2 OR 9a It is.

[0471] Embodiment 66 is a compound according to embodiment 65, wherein R 9a is hydrogen or -CH 3 It is.

[0472] Embodiment 67 is a compound according to embodiment 66, wherein each R 9a is hydrogen.

[0473] Embodiment 68 is a compound of embodiment 66, wherein each R 9a -CH 3 It is.

[0474] Embodiment 69 is a compound according to any one of embodiments 47 to 68, wherein each R 6c and R 6d are independently halogen and -CH 3 is selected from.

[0475] Embodiment 70 is a compound according to any one of embodiments 47 to 69, wherein each R 3a and R 3b -CH 3 It is.

[0476] Embodiment 71 is a compound according to any one of embodiments 47 to 70, wherein R 11a is hydrogen or -CH 3 It is.

[0477] Embodiment 72 is a compound according to embodiment 71, wherein R 11a -CH 3 It is.

[0478] Embodiment 73 is a compound according to any one of embodiments 47 to 72, wherein R 12a is hydrogen or -CH 3 It is.

[0479] Embodiment 74 is a compound according to embodiment 73, wherein R 12a -CH 3 It is.

[0480] Embodiment 75 is a compound according to any one of embodiments 47 to 74, wherein each R 11b , R 11c , R 12b , and R 12c is hydrogen.

[0481] Embodiment 76 is a copolymer, the copolymer comprising: a) a repeating unit of formula (VII): [ka] (In the formula, Each R 1a and R 1b is independently selected from hydrogen and halogen; Each R 2a and R 2b are independently selected from halogen, -CN, and optionally substituted C 1 -C 6 fluoroalkyl; Each A 1 and A 2 are independently -C(=O)-, -S(=O)-, -S(=O) 2 - and -S(=O)(=NR 3c )- is selected from Each B 1 and B. 2 are independently -O- and -NR 3c - selected from Z 1 is -(CR 6c R 6d ) s - and Each R 4c , R 4d , R 5d , R 5e , R 6c , and R 6d are independently hydrogen, halogen, -CN, -OR 9a , optionally substituted C 1 -C 4 Alkyl, optionally substituted C 1 -C 4 Fluoroalkyl, optionally substituted C 2 -C 6 Alkenyl, -NR 3c R 3d , -S(=O) 2 O - , -S(=O) 2 OR 9a , -C(=O)O - , and -C(=O)OR 9a is selected from Each R3c and R 3d are independently hydrogen, optionally substituted C 1 -C 4 Alkyl, -X-optionally substituted C 1 -C 4 Alkyl, optionally substituted C 2 -C 6 alkenyl, and optionally substituted aryl; X is -C(=O)-, -S(=O)-, or -S(=O) 2 - and Each R 9a , R 11a , R 11b , and R 11c are independently hydrogen, optionally substituted C 1 -C 4 alkyl, and optionally substituted aryl; n is an integer selected from 0, 1, 2, 3, 4, 5, 6, 7, and 8; s is an integer selected from 1, 2, 3, 4, and 5; b) A repeating unit of formula (VIII): [ka] (In the formula, A 3 -C(=O)-, -S(=O)-, -S(=O) 2 - or -S(=O)(=NR 3c )-and B 3 is -O- or -NR 3c - and D is -S(=O) 2 O - , -S(=O) 2 OR 9a , -C(=O)O - , or -C(=O)OR 9a and Z 2 is -(CR 6c R 6d ) t - and Z3 is -(CR 6c R 6d ) p - and Each R 3a and R 3b are independently hydrogen, optionally substituted C 1 -C 4 alkyl, and optionally substituted benzyl; Each R 6c and R 6d are independently hydrogen, halogen, -CN, -OR 9a , optionally substituted C 1 -C 4 Alkyl, optionally substituted C 1 -C 4 Fluoroalkyl, optionally substituted C 2 -C 6 Alkenyl, -NR 3c R 3d , -S(=O) 2 O - , -S(=O) 2 OR 9a , -C(=O)O - , and -C(=O)OR 9a is selected from Each R 3c and R 3d are independently hydrogen, optionally substituted C 1 -C 4 Alkyl, -X-optionally substituted C 1 -C 4 Alkyl, optionally substituted C 2 -C 6 alkenyl, and optionally substituted aryl; X is -C(=O)-, -S(=O)-, or -S(=O) 2 - and Each R 9a , R 12a , R 12b , and R 12c are independently hydrogen, optionally substituted C 1 -C 4 alkyl, and optionally substituted aryl; t is an integer selected from 1, 2, 3, 4, or 5; p is an integer selected from 1, 2, 3, 4, or 5; A repeat unit of formula (VIII), wherein the repeat unit of formula (VIII) is charged or zwitterionic; c) A repeating unit of formula (IX): [ka] (A 4 -C(=O)-, -S(=O)-, -S(=O) 2 - or -S(=O)(=NR 3c )-and B 4 is -O- or -NR 3c - and Z 4 is -(CR 6c R 6d ) k - and E is -CN, -OR 9a , -NR 9a R 9b , -NR 9a R 9b R 9c+ , optionally substituted C 1 -C 4 Alkyl, optionally substituted C 1 -C 6 Fluoroalkyl, -S(=O) 2 O - , -S(=O) 2 OR 9a , -C(=O)O - , or -C(=O)OR 9a and Each R 6c and R 6d are independently hydrogen, halogen, -CN, -OR 9a , optionally substituted C 1 -C 4 Alkyl, optionally substituted C 1 -C 4 Fluoroalkyl, optionally substituted C 2 -C 6Alkenyl, -NR 3c R 3d , -S(=O) 2 O - , -S(=O) 2 OR 9a , -C(=O)O - , and -C(=O)OR 9a is selected from Each R 3c and R 3d are independently hydrogen, optionally substituted C 1 -C 4 Alkyl, -X-optionally substituted C 1 -C 4 Alkyl, optionally substituted C 2 -C 6 alkenyl, and optionally substituted aryl; X is -C(=O)-, -S(=O)-, or -S(=O) 2 - and Each R 9a , R 9b , R 9c , R 13a , R 13b , and R 13c are independently hydrogen, optionally substituted C 1 -C 4 alkyl, and optionally substituted aryl; k is an integer selected from 1, 2, 3, 4, or 5.

[0482] Embodiment 77 is the copolymer of embodiment 76, wherein each R 1a and R 1b are independently halogen.

[0483] Embodiment 78 is the copolymer of embodiment 76 or 77, wherein each R 1a and R 1b is independently F or Cl.

[0484] Embodiment 79 is the copolymer of any one of embodiments 76 to 78, wherein each R 1a and R1b is F.

[0485] Embodiment 80 is the copolymer of any one of embodiments 76 to 79, wherein each R 2a and R 2b are independently halogen, -CN, and -CF 3 is selected from.

[0486] Embodiment 81 is the copolymer of any one of embodiments 76 to 80, wherein each R 2a and R 2b are independently F, Cl, -CN, and -CF 3 is selected from.

[0487] Embodiment 82 is the copolymer of any one of embodiments 76 to 81, wherein each R 2a and R 2b is F.

[0488] Embodiment 83 is the copolymer of any one of embodiments 76 to 82, 1 is -S(=O) 2 - and each A 2 , A 3 , and A 4 is -C(=O)-.

[0489] Embodiment 84 is the copolymer of any one of embodiments 76 to 83, wherein each B 1 , B 2 , and B. 3 are independently -O- or -NR 3c -It is.

[0490] Embodiment 85 is the copolymer of any one of embodiments 76 to 84, wherein R 3c is hydrogen or -CH 3 It is.

[0491] Embodiment 86 is the copolymer of any one of embodiments 76 to 85, wherein D is -S(=O) 2 O -or -C(=O)O - It is.

[0492] Embodiment 87 is the copolymer of any one of embodiments 76 to 86, wherein E is -NR 9a R 9b R 9c+ or -S(=O) 2 OR 9a It is.

[0493] Embodiment 88 is the copolymer of any one of embodiments 76 to 87, wherein each R 9a , R 9b , and R 9c are independently hydrogen or C 1 -C 4 It is an alkyl.

[0494] Embodiment 89 is the copolymer of any one of embodiments 76 to 88, wherein each R 3a and R 3b -CH 3 It is.

[0495] Embodiment 90 is the copolymer of any one of embodiments 76 to 89, wherein each R 4c , R 4d , R 5d , and R 5e is hydrogen.

[0496] Embodiment 91 is the copolymer of any one of embodiments 76 to 90, wherein each R 3c , R 3d , R 6c , and R 6d is hydrogen.

[0497] Embodiment 92 is the copolymer of any one of embodiments 76 to 91, wherein each R 11a , R 12a , and R 13a is hydrogen or -CH 3 It is.

[0498] Embodiment 93 is the copolymer of any one of embodiments 76 to 92, wherein each R 11b , R 11c , R 12b , R 12c , R 13b , and R 13c is hydrogen.

[0499] Embodiment 94 is the copolymer of any one of embodiments 76-93, wherein n is 0, 1, or 2.

[0500] Embodiment 95 is the copolymer of any one of embodiments 76-94, wherein each s, t, p, and k is independently 1, 2, or 3.

[0501] Embodiment 96 is a medical device coated with a compound according to any one of embodiments 1 to 95.

[0502] Embodiment 97 is a biofouling resistant medical device, the surface of which is coated with a phenylazide-based copolymer having a number average molecular weight of about 10,000 to about 250,000.

[0503] Embodiment 98 is the biofouling-resistant medical device of embodiment 97, wherein the phenyl azide-based copolymer has a number average molecular weight of about 10,000 to about 20,000.

[0504] Embodiment 99 is the biofouling-resistant medical device of embodiment 97, wherein the phenyl azide-based copolymer has a number average molecular weight of about 10,000 to about 40,000.

[0505] Embodiment 100 is the biofouling resistant medical device of embodiment 97, wherein the phenyl azide-based copolymer has a number average molecular weight of about 20,000 to about 60,000.

[0506] Embodiment 101 is the biofouling-resistant medical device of embodiment 97, wherein the phenyl azide-based copolymer has a number average molecular weight of about 40,000 to about 100,000.

[0507] Embodiment 102 is the biofouling-resistant medical device of embodiment 97, wherein the phenyl azide-based copolymer has a number average molecular weight of about 80,000 to about 160,000.

[0508] Embodiment 103 is the biofouling-resistant medical device of embodiment 97, wherein the phenyl azide-based copolymer has a number average molecular weight of about 120,000 to about 200,000.

[0509] Embodiment 104 is the biofouling-resistant medical device of embodiment 97, wherein the phenyl azide-based copolymer has a number average molecular weight of about 14,000 to about 21,000.

[0510] Embodiment 105 is the biofouling-resistant medical device of embodiment 97, wherein the phenyl azide-based copolymer has a number average molecular weight of about 15,000 to about 18,000.

[0511] Embodiment 106 is a biofouling-resistant medical device according to any one of embodiments 97 to 105, wherein the phenyl azide-based copolymer is a compound according to any one of embodiments 24 to 75 or a copolymer according to any one of embodiments 76 to 95.

[0512] Embodiment 107 is a biofouling resistant medical device, the surface of the medical device is coated with a phenyl azide-based copolymer having a polydispersity index (PDI) of about 1 to about 1.5.

[0513] Embodiment 108 is a biofouling resistant medical device according to embodiment 107, wherein the PDI is about 1.4, 1.3, 1.2, or 1.1.

[0514] Embodiment 109 is a biofouling resistant medical device according to embodiment 107, wherein the PDI is about 1.19.

[0515] Embodiment 110 is a biofouling resistant medical device according to any one of embodiments 97 to 109, wherein the medical device comprises a dental instrument or a medical instrument.

[0516] Embodiment 111 is a biofouling resistant medical device according to any one of embodiments 97 to 110, wherein the medical device comprises an implant, an IV, a prosthesis, a suture material, a valve, a stent, a catheter, a rod, a shunt, a scope, a contact lens, tubing, wiring, an electrode, a clip, a fastener, a syringe, a container, or a combination thereof.

[0517] Embodiment 112 is a biofouling resistant medical device according to embodiment 111, wherein the medical device is a contact lens.

[0518] Embodiment 113 is a biofouling-resistant medical device according to embodiment 111, wherein the medical device is a catheter.

[0519] Embodiment 114 is a biofouling-resistant medical device according to embodiment 113, wherein the catheter is an indwelling catheter.

[0520] Embodiment 115 is a biofouling-resistant medical device according to embodiment 113, wherein the catheter comprises a ureteral catheter or a Foley catheter.

[0521] Embodiment 116 is a biofouling-resistant medical device according to embodiment 111, wherein the medical device is a scope.

[0522] Embodiment 117 is a biofouling-resistant medical device as described in embodiment 116, wherein the scope comprises a scope utilized in image-guided surgery.

[0523] Embodiment 118 is a biofouling-resistant medical device as described in embodiment 116, wherein the scope comprises a scope utilized in endoscopy or laparoscopy.

[0524] Embodiment 119 is a biofouling resistant medical device according to embodiment 110 or 111, wherein the medical device comprises a hearing aid, an artificial larynx, a dental implant, a breast implant, a penile implant, a cranial / facial tendon, a tendon, a ligament, a meniscus, or an intervertebral disc.

[0525] Embodiment 120 is a biofouling resistant medical device according to any one of embodiments 110, 111, or 119, wherein the medical device comprises an artificial bone, an artificial joint, or an artificial organ.

[0526] Embodiment 121 is a biofouling resistant medical device according to embodiment 120, wherein the artificial organ comprises an artificial pancreas, an artificial heart, an artificial limb, or a heart valve.

[0527] Embodiment 122 is a biofouling resistant medical device according to any one of embodiments 97 to 109, wherein the medical device comprises a bandage or patch.

[0528] Embodiment 123 is a biofouling resistant medical device according to any one of embodiments 107 to 122, wherein the phenyl azide-based copolymer comprises a compound according to any one of embodiments 1 to 75, or a copolymer according to any one of embodiments 76 to 95.

[0529] Embodiment 124 is a biofouling resistant medical device according to any one of embodiments 107 to 122, wherein the copolymer comprises a zwitterionic copolymer.

[0530] Embodiment 125 is a biofouling resistant medical device according to embodiment 124, wherein the zwitterionic copolymer is polysulfobetaine.

[0531] Embodiment 126 is a biofouling-resistant medical device according to any one of embodiments 107 to 125, wherein the biofouling is caused by bacteria, viruses, and / or fungi.

[0532] Embodiment 127 is a method of making a biofouling resistant medical device, the method comprising: a) contacting a surface of a medical device with a solution or suspension comprising a charged or zwitterionic copolymer; b) treating the surface of the medical device of step a) with a light source for a time sufficient to effect photo-grafting of a charged or zwitterionic copolymer onto the surface of the medical device, thereby producing a biofouling resistant medical device; The charged or zwitterionic copolymers include phenyl azide-based copolymers, the charged or zwitterionic copolymers having a number average molecular weight of about 10,000 to about 250,000.

[0533]

[00131] Embodiment 128 is a method of making a charged or zwitterionic copolymer modified biofouling resistant device, the method comprising: a) contacting a surface of a silicon-based device with a solution or suspension comprising a charged or zwitterionic copolymer; b) treating the surface of the device of step a) with a light source for a time sufficient to effect photo-grafting of a charged or zwitterionic copolymer onto the surface of the silicon-based device, thereby producing a charged or zwitterionic modified device; Charged or zwitterionic copolymers include phenylazide-based copolymers.

[0534]

[00131] Embodiment 129 is a method of making a charged or zwitterionic copolymer modified biofouling resistant device, the method comprising: a) contacting the surface of the device with a solution or suspension comprising a charged or zwitterionic copolymer; b) treating the surface of the device of step a) with a light source for a time sufficient to effect photo-grafting of a charged or zwitterionic copolymer onto the surface of the device, thereby producing a charged or zwitterionic modified device; Charged or zwitterionic copolymers include phenyl azide-based copolymers; The charged or zwitterionic copolymers have a number average molecular weight of about 10,000 to about 250,000.

[0535] Embodiment 130 is a method according to any one of embodiments 127 to 129, wherein the time sufficient for photografting is at least 1 minute, at least 2 minutes, 3 minutes, 4 minutes, 5 minutes, 6 minutes, 7 minutes, 8 minutes, 9 minutes, 10 minutes, 15 minutes, 20 minutes, 25 minutes, or 30 minutes.

[0536] Embodiment 131 is the method of any one of embodiments 127 to 130, wherein the light source is an ultraviolet light source.

[0537] Embodiment 132 is the method of embodiment 131, wherein the ultraviolet light source has a wavelength of at least 900 μW / cm 2 It has a strength of.

[0538] Embodiment 133 is the method of embodiment 131 or 132, wherein the ultraviolet light source has a wavelength of 240 nm to 280 nm, 240 nm to 275 nm, 240 nm to 270 nm, 240 nm to 265 nm, 240 nm to 260 nm, 240 nm to 255 nm, 240 nm to 250 nm, 240 nm to 245 nm, 250 nm to 280 nm, 250 nm to 275 nm, 250 nm to 270 nm, 250 nm to 265 nm, 250 nm to 260 nm, 255 nm to 280 nm, 255 nm to 275 nm, 255 nm to 270 nm, 255 nm to 265 nm, 255 nm to 260 nm, 260 nm to 280 nm, 260 nm to 275 nm, 260 nm to 270 nm, or 270 nm to 280 nm.

[0539] Embodiment 134 is the method of embodiment 131 or 132, wherein the ultraviolet light source has a wavelength of at least 240 nm, 245 nm, 250 nm, 251 nm, 252 nm, 253 nm, 254 nm, 255 nm, 256 nm, 257 nm, 258 nm, 259 nm, 260 nm, 261 nm, 262 nm, 263 nm, 264 nm, 265 nm, 266 nm, 267 nm, 268 nm, 269 nm, 270 nm, 275 nm, or 280 nm.

[0540] Embodiment 135 is the method of any one of embodiments 127 to 134, wherein the solution or suspension in step a) is an aqueous solution or aqueous suspension.

[0541] Embodiment 136 is the method according to any one of embodiments 127 to 135, wherein the photografting in step b) is not affected by the presence of oxygen.

[0542] Embodiment 137 is the method of any one of embodiments 127-136, wherein the charged or zwitterionic copolymer is a compound of any one of embodiments 24-75, or a copolymer of any one of embodiments 76-95.

[0543] Embodiment 138 is the method of any one of embodiments 127 to 137, wherein the solution or suspension comprising the charged or zwitterionic copolymer has a concentration of the charged or zwitterionic copolymer in the solution or suspension of 1 mg / mL to 30 mg / mL.

[0544] Embodiment 139 is the method of embodiment 138, wherein the concentration of the charged or zwitterionic copolymer in the solution or suspension is from 1 mg / mL to 25 mg / mL, from 1 mg / mL to 20 mg / mL, from 1 mg / mL to 15 mg / mL, from 1 mg / mL to 10 mg / mL, from 1 mg / mL to 5 mg / mL, from 5 mg / mL to 30 mg / mL, from 5 mg / mL to 25 mg / mL, from 5 mg / mL to 20 mg / mL, from 5 mg / mL to 5 ... g / mL~15mg / mL, 5mg / mL~10mg / mL, 10mg / mL~30mg / mL, 10mg / mL~25mg / mL, 10mg / mL~20mg / mL, 10mg / mL~15mg / mL, 15 mg / mL to 30 mg / mL, 15 mg / mL to 25 mg / mL, 15 mg / mL to 20 mg / mL, 20 mg / mL to 30 mg / mL, or 20 mg / mL to 25 mg / mL.

[0545] Embodiment 140 is the method of embodiment 138, wherein the concentration of the charged or zwitterionic copolymer in the solution or suspension is about 1 mg / mL, 2 mg / mL, 3 mg / mL, 4 mg / mL, 5 mg / mL, 6 mg / mL, 7 mg / mL, 8 mg / mL, 9 mg / mL, 10 mg / mL, 11 mg / mL, 12 mg / mL, 13 mg / mL, 14 mg / mL, 15 mg / mL, 16 mg / mL, 17 mg / mL, 18 mg / mL, 19 mg / mL, 20 mg / mL, 21 mg / mL, 22 mg / mL, 23 mg / mL, 24 mg / mL, 25 mg / mL, 26 mg / mL, 27 mg / mL, 28 mg / mL, 29 mg / mL, or 30 mg / mL.

[0546] Embodiment 141 is the method of any one of embodiments 127 to 140, wherein the concentration of the charged or zwitterionic copolymer is 0.1 to 1 mg per square centimeter of the device.

[0547] Embodiment 142 is the method of embodiment 128, wherein the charged or zwitterionic copolymer has a number average molecular weight of about 10,000 to about 250,000.

[0548] Embodiment 143 is the method of any one of embodiments 127 or 129-142, wherein the charged or zwitterionic copolymer has a number average molecular weight of about 10,000 to about 20,000.

[0549] Embodiment 144 is the method of any one of embodiments 127 or 129-142, wherein the charged or zwitterionic copolymer has a number average molecular weight of about 10,000 to about 40,000.

[0550] Embodiment 145 is the method of any one of embodiments 127 or 129-142, wherein the charged or zwitterionic copolymer has a number average molecular weight of about 20,000 to about 60,000.

[0551] Embodiment 146 is the method of any one of embodiments 127 or 129-142, wherein the charged or zwitterionic copolymer has a number average molecular weight of about 40,000 to about 100,000.

[0552] Embodiment 147 is the method of any one of embodiments 127 or 129-142, wherein the charged or zwitterionic copolymer has a number average molecular weight of about 80,000 to about 160,000.

[0553] Embodiment 148 is the method of any one of embodiments 127 or 129-142, wherein the charged or zwitterionic copolymer has a number average molecular weight of about 120,000 to about 200,000.

[0554] Embodiment 149 is the method of any one of embodiments 127 or 129-142, wherein the charged or zwitterionic copolymer has a number average molecular weight of about 14,000 to about 21,000.

[0555] Embodiment 150 is the method of any one of embodiments 127 or 129-142, wherein the charged or zwitterionic copolymer has a number average molecular weight of about 15,000 to about 18,000.

[0556] Embodiment 151 is the method of embodiment 127 or 129, in which the device comprises a carbon-based device or a silicon-based device.

[0557] Embodiment 152 is the method of embodiment 151, in which the device comprises a silicon-based device.

[0558] Embodiment 153 is the method of embodiment 128 or 152, wherein the silicon based device comprises a silicon based polymer portion.

[0559] Embodiment 154 is the method of embodiment 153, in which the silicon-based polymer moiety comprises a siloxane polymer moiety, a sesquisiloxane polymer moiety, a siloxane-silarylene polymer moiety, a silalkylene polymer moiety, a polysilane moiety, a polysilylene moiety, or a polysilazane moiety.

[0560] Embodiment 155 is the method of embodiment 154, wherein the silicon-based device comprises a siloxane polymer portion.

[0561] Embodiment 156 is the method of embodiment 151, in which the device comprises a carbon-based device.

[0562] Embodiment 157 is the method of embodiment 156, in which the carbon-based device comprises a carbon-based polymer.

[0563] Embodiment 158 ​​is the method of embodiment 156, wherein the carbon-based device comprises a polyolefin portion.

[0564] Embodiment 159 is the method of embodiment 158, wherein the polyolefin portion comprises a polyethylene portion, a polypropylene portion, a polyvinyl chloride portion, a polyvinylidene fluoride portion, a polytetrafluoroethylene portion, a polychlorotrifluoroethylene portion, or a polystyrene portion.

[0565] Embodiment 160 is the method of embodiment 157, in which the carbon-based polymer comprises a polyamide portion, a polyurethane portion, a phenol-formaldehyde resin portion, a polycarbonate portion, a polychloroprene portion, a polyacrylonitrile portion, a polyimide portion, or a polyester portion.

[0566] Embodiment 161 is the method of embodiment 157, in which the carbon-based polymer comprises nylon.

[0567] Embodiment 162 is the method of embodiment 157, wherein the carbon-based polymer comprises polyethylene terephthalate.

[0568] Embodiment 163 is the method of any one of embodiments 127 to 162, wherein the copolymer comprises a zwitterionic copolymer.

[0569] Embodiment 164 is the method of embodiment 163, in which the zwitterionic copolymer is polysulfobetaine.

[0570] Embodiment 165 is the method of any one of embodiments 127 to 164, wherein the biofouling is caused by bacteria, viruses, and / or fungi.

[0571] Embodiment 166 is a method for synthesizing a compound of formula (II), the method comprising reacting a compound of formula (IV), or a salt or solvate thereof, with a compound of formula (V): [ka] During the ceremony, Each R 1a and R 1b is independently selected from hydrogen and halogen; Each R 2a and R 2b are independently selected from halogen, -CN, and optionally substituted C 1 -C 6 fluoroalkyl; Each A1 , A 2 , and A 3 are independently -C(=O)-, -S(=O)-, -S(=O) 2 - and -S(=O)(=NR 3c )- is selected from Each B 1 , B 2 , and B. 3 are independently -O- and -NR 3c - selected from D is -S(=O) 2 O - , -S(=O) 2 OR 9a , -C(=O)O - , or -C(=O)OR 9a and Z 1 is -(CR 6c R 6d ) s - and Z 2 is -(CR 6c R 6d ) t - and Z 3 is -(CR 6c R 6d ) p - and Each R 3a and R 3b are independently hydrogen, optionally substituted C 1 -C 4 alkyl, and optionally substituted benzyl; Each R 4c , R 4d , R 5d , R 5e , R 6c , and R 6d are independently hydrogen, halogen, -CN, -OH, optionally substituted C 1 -C 4 Alkyl, optionally substituted C 1 -C 4 Fluoroalkyl, optionally substituted C 2 -C 6 Alkenyl, -NR 3cR 3d , -S(=O) 2 O - , -S(=O) 2 OR 9a , -C(=O)O - , and -C(=O)OR 9a is selected from Each R 3c and R 3d are independently hydrogen, optionally substituted C 1 -C 4 Alkyl, -X-optionally substituted C 1 -C 4 Alkyl, optionally substituted C 2 -C 6 alkenyl, and optionally substituted aryl; X is -C(=O)-, -S(=O)-, or -S(=O) 2 - and Each R 9a , R 11a , R 11b , R 11c , R 12a , R 12b , and R 12c are independently hydrogen, optionally substituted C 1 -C 4 alkyl, and optionally substituted aryl; n is an integer selected from 0, 1, 2, 3, 4, 5, 6, 7, and 8; s is an integer selected from 1, 2, 3, 4, or 5; t is an integer selected from 1, 2, 3, 4, or 5; p is an integer selected from 1, 2, 3, 4, or 5; x is 0.001 to 0.999, The compounds of formula (II) and formula (V) are each independently charged or zwitterionic, However, the compound of formula (II) [ka] isn't it.

[0572] Embodiment 167 is the method of embodiment 166, wherein each R 1a and R 1b are independently halogen.

[0573] Embodiment 168 is the method of embodiment 166 or 167, wherein each R 1a and R 1b is independently F or Cl.

[0574] Embodiment 169 is the method of any one of embodiments 166 to 168, further comprising: 1a and R 1b are each F.

[0575] Embodiment 170 is the method of any one of embodiments 166 to 169, wherein each R 2a and R 2b are independently halogen, -CN, and -CF 3 is selected from.

[0576] Embodiment 171 is the method of any one of embodiments 166 to 170, wherein each R 2a and R 2b are independently F, Cl, -CN, and -CF 3 is selected from.

[0577] Embodiment 172 is the method of any one of embodiments 166 to 171, further comprising: 2a and R 2b are each F.

[0578] Embodiment 173 is the method according to any one of embodiments 166 to 172, further comprising: 1 is -S(=O) 2 - and A 2 is -C(=O)-, and A 3 is -C(=O)-.

[0579] Embodiment 174 is the method according to any one of embodiments 166 to 173, further comprising: 1and B. 2 are respectively, -NR 3c -It is.

[0580] Embodiment 175 is the method of embodiment 174, wherein R 3c is hydrogen or -CH 3 It is.

[0581] Embodiment 176 is the method of embodiment 175, wherein R 3c is hydrogen.

[0582] Embodiment 177 is the method according to any one of embodiments 166 to 176, further comprising: 3 is -O-.

[0583] Embodiment 178 is the method of any one of embodiments 166 to 177, wherein D is -S(=O) 2 OR 9a OR -C(=O)OR 9a It is.

[0584] Embodiment 179 is the method of embodiment 178, wherein R 9a is hydrogen or -CH 3 It is.

[0585] Embodiment 180 is the method of any one of embodiments 166 to 177, wherein D is -S(=O) 2 O - or -C(=O)O - It is.

[0586] Embodiment 181 is the method of embodiment 180, wherein D is -S(=O) 2 O - It is.

[0587] Embodiment 182 is the method of any one of embodiments 166 to 181, wherein each R 6c and R 6d is hydrogen.

[0588] Embodiment 183 is the method of any one of embodiments 166 to 182, wherein each R 3a and R 3b -CH 3 It is.

[0589] Embodiment 184 is the method of any one of embodiments 166 to 183, further comprising: 11a is hydrogen or -CH 3 It is.

[0590] Embodiment 185 is the method of embodiment 184, wherein R 11a -CH 3 It is.

[0591] Embodiment 186 is the method of any one of embodiments 166 to 185, further comprising: 12a is hydrogen or -CH 3 It is.

[0592] Embodiment 187 is the method of embodiment 186, wherein R 12a -CH 3 It is.

[0593] Embodiment 188 is the method of any one of embodiments 166 to 187, wherein each R 11b , R 11c , R 12b , and R 12c is hydrogen.

[0594] Embodiment 189 is a method for synthesizing a compound of formula (III), the method comprising reacting a compound of formula (IV), or a salt or solvate thereof, with a compound of formula (VI): [ka] During the ceremony, Each R 1a and R 1b is independently selected from hydrogen and halogen; Each R 2a and R 2bare independently selected from halogen, -CN, and optionally substituted C 1 -C 6 fluoroalkyl; Each A 1 , A 2 , and A 3 are independently -C(=O)-, -S(=O)-, -S(=O) 2 - and -S(=O)(=NR 3c )- is selected from Each B 1 , B 2 , and B. 3 are independently -O- and -NR 3c - selected from Z 1 is -(CR 6c R 6d ) s - and Z 2 is -(CR 6c R 6d ) t - and E is -CN, -OR 9a , -NR 9a R 9b , -NR 9a R 9b R 9c+ , optionally substituted C 1 -C 4 Alkyl, optionally substituted C 1 -C 6 Fluoroalkyl, -S(=O) 2 O - , -S(=O) 2 OR 9a , -C(=O)O - , or -C(=O)OR 9a and Each R 4c , R 4d , R 5d , R 5e , R 6c , and R 6d are independently hydrogen, halogen, -CN, -OR 9a , optionally substituted C 1 -C 4 Alkyl, optionally substituted C1 -C 4 Fluoroalkyl, optionally substituted C 2 -C 6 Alkenyl, -NR 3c R 3d , -S(=O) 2 O - , -S(=O) 2 OR 9a , -C(=O)O - , and -C(=O)OR 9a is selected from Each R 3c and R 3d are independently hydrogen, optionally substituted C 1 -C 4 Alkyl, -X-optionally substituted C 1 -C 4 Alkyl, optionally substituted C 2 -C 6 alkenyl, and optionally substituted aryl; X is -C(=O)-, -S(=O)-, or -S(=O) 2 - and Each R 9a , R 9b , R 9c , R 11a , R 11b , R 11c , R 12a , R 12b , and R 12c are independently hydrogen, optionally substituted C 1 -C 4 alkyl, and optionally substituted aryl; n is an integer selected from 0, 1, 2, 3, 4, 5, 6, 7, and 8; s is an integer selected from 1, 2, 3, 4, or 5; t is an integer selected from 1, 2, 3, 4, or 5; x is between 0.001 and 0.999.

[0595] Embodiment 190 is the method of embodiment 189, wherein each R 1a and R 1bare independently halogen.

[0596] Embodiment 191 is the method of embodiment 189 or 190, wherein each R 1a and R 1b is independently F or Cl.

[0597] Embodiment 192 is the method of any one of embodiments 189 to 191, further comprising: 1a and R 1b are each F.

[0598] Embodiment 193 is the method of any one of embodiments 1...

Claims

1. A copolymer comprising: a) A repeating unit of formula (VII): 【Chemistry 104】 (In the formula, Each R １ａ and R １ｂ is independently selected from hydrogen and halogen; Each R ２ａ and R ２ｂ are independently selected from halogen, —CN, and optionally substituted C １ -C ６ fluoroalkyl; Each A １ and A ２ are independently -C(=O)-, -S(=O)-, -S(=O) ２ -, and -S(=O)(=NR ３ｃ ) - is selected from Each B １ and B ２ are independently —O— and —NR ３ｃ - selected from Z １ is -(CR ６ｃ R ６ｄ ) ｓ - and Each R ４ｃ , R ４ｄ , R ５ｄ , R ５ｅ , R ６ｃ , and R ６ｄ are independently hydrogen, halogen, -CN, -OR ９ａ , optionally substituted C １ -C ４ Alkyl, optionally substituted C １ -C ４ Fluoroalkyl, optionally substituted C ２ -C ６ Alkenyl, -NR ３ｃ R ３ｄ , -S(=O) ２ O － , -S(=O) ２ OR ９ａ , -C(=O)O － and -C(=O)OR ９ａ is selected from Each R ３ｃ and R ３ｄ are independently hydrogen, optionally substituted C １ -C ４ Alkyl, -X-optionally substituted C １ -C ４ Alkyl, optionally substituted C ２ -C ６ alkenyl, and optionally substituted aryl; X is -C(=O)-, -S(=O)-, or -S(=O) ２ - and Each R ９ａ , R １１ａ , R １１ｂ , and R １１ｃ are independently hydrogen, optionally substituted C １ -C ４ alkyl, and optionally substituted aryl; n is an integer selected from 0, 1, 2, 3, 4, 5, 6, 7, and 8; s is an integer selected from 1, 2, 3, 4, and 5; b) A repeat unit of formula (VIII): 【Chemistry 105】 (In the formula, A ３ is -C(=O)-, -S(=O)-, -S(=O) ２ - or -S(=O)(=NR ３ｃ ) - and B ３ is -O- or -NR ３ｃ - and D is -S(=O) ２ O － , -S(=O) ２ OR ９ａ , -C(=O)O － or -C(=O)OR ９ａ and Z ２ is -(CR ６ｃ R ６ｄ ) ｔ - and Z ３ is -(CR ６ｃ R ６ｄ ) ｐ - and Each R ３ａ and R ３ｂ are independently hydrogen, optionally substituted C １ -C ４ alkyl, and optionally substituted benzyl; Each R ６ｃ and R ６ｄ are independently hydrogen, halogen, -CN, -OR ９ａ , optionally substituted C １ -C ４ Alkyl, optionally substituted C １ -C ４ Fluoroalkyl, optionally substituted C ２ -C ６ Alkenyl, -NR ３ｃ R ３ｄ , -S(=O) ２ O － , -S(=O) ２ OR ９ａ , -C(=O)O － and -C(=O)OR ９ａ is selected from Each R ３ｃ and R ３ｄ are independently hydrogen, optionally substituted C １ -C ４ Alkyl, -X-optionally substituted C １ -C ４ Alkyl, optionally substituted C ２ -C ６ alkenyl, and optionally substituted aryl; X is -C(=O)-, -S(=O)-, or -S(=O) ２ - and Each R ９ａ , R １２ａ , R １２ｂ , and R １２ｃ are independently hydrogen, optionally substituted C １ -C ４ alkyl, and optionally substituted aryl; t is an integer selected from 1, 2, 3, 4, or 5; p is an integer selected from 1, 2, 3, 4, or 5; A repeat unit of formula (VIII), wherein the repeat unit of formula (VIII) is charged or zwitterionic; c) A repeating unit of formula (IX): 【Chemistry 106】 (A ４ is -C(=O)-, -S(=O)-, -S(=O) ２ - or -S(=O)(=NR ３ｃ ) - and B ４ is -O- or -NR ３ｃ - and Z ４ is -(CR ６ｃ R ６ｄ ) ｋ - and E is -CN, -OR ９ａ , -NR ９ａ R ９ｂ , -NR ９ａ R ９ｂ R ９ｃ＋ , optionally substituted C １ -C ４ Alkyl, optionally substituted C １ -C ６ Fluoroalkyl, -S(=O) ２ O － , -S(=O) ２ OR ９ａ , -C(=O)O － or -C(=O)OR ９ａ and Each R ６ｃ and R ６ｄ are independently hydrogen, halogen, -CN, -OR ９ａ , optionally substituted C １ -C ４ Alkyl, optionally substituted C １ -C ４ Fluoroalkyl, optionally substituted C ２ -C ６ Alkenyl, -NR ３ｃ R ３ｄ , -S(=O) ２ O － , -S(=O) ２ OR ９ａ , -C(=O)O － and -C(=O)OR ９ａ is selected from Each R ３ｃ and R ３ｄ are independently hydrogen, optionally substituted C １ -C ４ Alkyl, -X-optionally substituted C １ -C ４ Alkyl, optionally substituted C ２ -C ６ alkenyl, and optionally substituted aryl; X is -C(=O)-, -S(=O)-, or -S(=O) ２ - and Each R ９ａ , R ９ｂ , R ９ｃ , R １３ａ , R １３ｂ , and R １３ｃ are independently hydrogen, optionally substituted C １ -C ４ alkyl, and optionally substituted aryl; and k is an integer selected from 1, 2, 3, 4, or 5.

2. Each R １ａ , R １ｂ , R ２ａ , and R ２ｂ The copolymer of claim 1 , wherein:

3. A １ But -S(=O) ２ - and each A ２ , A ３ , and A ４ The copolymer of claim 1 , wherein is —C(═O)—.

4. Each B １ , B ２ , and B ３ are independently -O- or -NR ３ｃ The copolymer of claim 1, wherein

5. Each R ３ｃ is hydrogen or -CH ３ The copolymer of claim 4 ,

6. D is -S(=O) ２ O － Or -C(=O)O － 2. The copolymer of claim 1 ,

7. E is -NR ９ａ R ９ｂ R ９ｃ＋ Or -S(=O) ２ OR ９ａ 2. The copolymer of claim 1 ,

8. Each R ９ａ , R ９ｂ , and R ９ｃ are independently hydrogen or C １ -C ４ The copolymer of claim 7, wherein the aryl group is an alkyl group.

9. Each R ３ａ and R ３ｂ But -CH ３ 2. The copolymer of claim 1 ,

10. Each R ３ｃ , R ３ｄ , R ４ｃ , R ４ｄ , R ５ｄ , R ５ｅ , R ６ｃ , and R ６ｄ The copolymer of claim 1 , wherein is hydrogen.

11. Each R １１ａ , R １２ａ , and R １３ａ is hydrogen or -CH ３ 2. The copolymer of claim 1 ,

12. Each R １１ｂ , R １１ｃ , R １２ｂ , R １２ｃ , R １３ｂ , and R １３ｃ The copolymer of claim 1 , wherein is hydrogen.

13. The copolymer of claim 1 , wherein n is 0, 1, or 2.

14. 2. The copolymer of claim 1, wherein each s, t, p, and k is independently 1, 2, or 3.

15. A medical device coated with the copolymer of claim 1.

16. A biofouling-resistant medical device, wherein a surface of the biofouling-resistant medical device is coated with the copolymer described in claim 1.

17. 17. The biofouling resistant medical device of claim 16, wherein the biofouling resistant medical device comprises an implant, an intravenous (IV) line, a prosthesis, a suture material, a valve, a stent, a catheter, a rod, a shunt, a scope, a contact lens, tubing, wiring, an electrode, a clip, a fastener, a syringe, a container, or a combination thereof.

18. 20. The biofouling resistant medical device of claim 17, wherein the biofouling resistant medical device is a catheter.

19. 17. The biofouling resistant medical device of claim 16, wherein the biofouling is caused by bacteria, viruses, and / or fungi.

20. A method for producing a biofouling resistant medical device according to any one of claims 16 to 19, comprising the steps of: a) contacting a surface of the device with a mixture comprising a charged or zwitterionic copolymer; b) treating the surface of the device of step a) with a heat source to effect thermal grafting of the copolymer onto the surface of the device, thereby creating the biofouling resistant device; The method of claim 1, wherein the charged or zwitterionic copolymer comprises a phenylazide-based copolymer, the charged or zwitterionic copolymer having a number average molecular weight of 10,000 to 250,000.

21. 21. The method of claim 20, wherein the treating with the heat source and thermal grafting is applied for 1 minute, 2 minutes, 3 minutes, 4 minutes, 5 minutes, 6 minutes, 7 minutes, 8 minutes, 9 minutes, 10 minutes, 15 minutes, 20 minutes, 25 minutes, 30 minutes, 45 minutes, 1 hour, 1.5 hours, 2 hours, 3 hours, 4 hours, 5 hours, 6 hours, 9 hours, 12 hours, 18 hours, or 24 hours.

22. 21. The method of claim 20, wherein the heat source provides a grafting temperature of 60°C to 80°C, 80°C to 100°C, 100°C to 120°C, 120°C to 140°C, 140°C to 160°C, 160°C to 180°C, 180°C to 200°C, 200°C to 220°C, or 220°C to 240°C.

23. 21. The method of claim 20, wherein the solution or suspension in step a) is an aqueous solution or suspension.

24. 21. The method of claim 20, wherein the thermal grafting of step b) is unaffected by the presence of oxygen.

25. 21. The method of claim 20, wherein the charged or zwitterionic copolymer is a copolymer according to claim 1.

26. The method of claim 20, wherein the solution or suspension containing the charged or zwitterionic copolymer has a concentration of the charged or zwitterionic copolymer in the solution or suspension of 1 mg / mL to 30 mg / mL.

27. 21. The method of claim 20, wherein the concentration of the charged or zwitterionic copolymer in the solution or suspension is 1 mg / mL to 25 mg / mL, 1 mg / mL to 20 mg / mL, 1 mg / mL to 15 mg / mL, 1 mg / mL to 10 mg / mL, 1 mg / mL to 5 mg / mL, 5 mg / mL to 30 mg / mL, 5 mg / mL to 25 mg / mL, 5 mg / mL to 20 mg / mL, 5 mg / mL to 15 mg / mL, 5 mg / mL to 10 mg / mL, 10 mg / mL to 30 mg / mL, 10 mg / mL to 25 mg / mL, 10 mg / mL to 20 mg / mL, 10 mg / mL to 15 mg / mL, 15 mg / mL to 30 mg / mL, 15 mg / mL to 25 mg / mL, 15 mg / mL to 20 mg / mL, 20 mg / mL to 30 mg / mL, or 20 mg / mL to 25 mg / mL.

28. The method of claim 20 , wherein the device comprises a carbon-based device or a silicon-based device.

29. The method of claim 20 , wherein the device comprises a silicon based device, the silicon based device comprising a silicon based polymer portion.

30. 21. The method of claim 20, wherein the biofouling is caused by bacteria, viruses, and / or fungi.

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