Amphiphilic polymer fluorescent material (PAF-G) and synthesis method thereof

Abstract

The invention relates to an amphiphilic polymer fluorescent material (PAF-G) and a synthesis method thereof, belonging to the technical field of chemical synthesis. The synthesis method of the PAF-G comprises the steps of firstly, synthesizing perfluorophenyl polyacrylate (PFPA) by using a reversible addition-fracture chain transfer method; then, carrying out an aminolysis reaction by using the PFPA, and grafting tetraphenyl ethylene and polyethylene glycol groups onto a polymer side chain according to a proportion so as to obtain the PAF-G. The assembly performance, water solubility and luminescence property of the PAF-G are regulated and controlled by regulating and controlling the length of a main polymer chain, the polymerization degree of the polyethylene glycol and the proportion ofthe two grafted groups. The molecular weight of the PFPA, the ratio of tetraphenyl ethylene to polyethylene glycol and the length of the polyethylene glycol have a wide regulation and control space; compared with small molecules, the PAF-G shows higher fluorescence intensity and fluorescence quantum yield; PAF-G assembly has good biocompatibility and can be applied to cell imaging.

Description

technical field

[0001] The invention relates to an amphiphilic polymer fluorescent material and a synthesis method thereof, in particular to a preparation method of a fluorescent dye and a water-soluble near-infrared fluorescent material with high fluorescence quantum yield and which can be used for biological imaging, belonging to chemical synthesis technology field. Background technique

[0002] Fluorescent materials that achieve the purpose of detection or imaging by marking biomolecules or cells are called fluorescent probe materials. Organic fluorescent materials have the advantages of flexible and diverse structures, adjustable luminescence position and intensity, and easy modification. They have become the preferred objects of fluorescent probe materials and have been widely studied. Organic aromatic fluorescent molecules usually show good fluorescence properties, but because most molecules have poor water solubility, it is particularly important to seek a simple and...

Examples

Embodiment 1

[0047] In this example, based on the methods of step 1 and step 2 of the present invention, alfa-amino polyethylene glycol with a chain length of 3 was used to synthesize and prepare the target molecule.

[0048] figure 1 The present invention relates to a synthetic route of PAF-G in an amphiphilic polymer fluorescent material and a synthetic method thereof.

[0049] In a round-bottomed flask, dissolve 2.5g of pentafluorophenol and 1.46g of 2,6-lutidine in dichloromethane, add 1.23g of acryloyl chloride to the mixture in an ice-water bath, and stir the reaction in an ice-water bath 3 hours, remove the ice-water bath and react at room temperature for 12 hours to obtain the crude product, filter with suction, save the filtrate, extract the filtrate with water twice, and use anhydrous MgSO 4 Carry out drying, remove solvent under reduced pressure, obtain crude product, use silica gel chromatography to crude product purification, obtain pentafluorophenol acryloyl chloride (PFPA),...

Embodiment 2

[0051] In this example, based on the methods of step 1 and step 2 of the present invention, alfa-amino polyethylene glycol with a chain length of 5 was used to synthesize and prepare the target molecule.

[0052] In a round-bottomed flask, dissolve 2.5g of pentafluorophenol and 2.91g of 2,6-lutidine in dichloromethane, add 3.69g of acryloyl chloride to the mixture in an ice-water bath, and stir the reaction in an ice-water bath After 5 hours, remove the ice-water bath and react at room temperature for 24 hours to obtain the crude product, filter it with suction, save the filtrate, extract the filtrate twice with water, and use anhydrous MgSO 4 Carry out drying, remove solvent under reduced pressure, obtain crude product, use silica gel chromatography to crude product purification, obtain PFPA, get 2.38g PFPA solution and 16.42mg azobisisobutyronitrile and 5.27mg4-cyano-4-(sulfur Benzoyl) valeric acid was mixed, the above reaction solution was freeze-thawed three times, and the...

Embodiment 3

[0055] In this example, based on the methods of step 1 and step 2 of the present invention, alfa-amino polyethylene glycol with a chain length of 9 was used to synthesize and prepare the target molecule.

[0056] In a round-bottomed flask, dissolve 2.5g of pentafluorophenol and 4.37g of 2,6-lutidine in dichloromethane, add 6.15g of acryloyl chloride to the above mixture, stir and react in an ice-water bath for 10 hours, remove React in an ice-water bath at room temperature for 48 hours to obtain a crude product, filter it with suction, save the filtrate, extract the filtrate twice with water, and use anhydrous MgSO 4 Carry out drying, remove solvent under reduced pressure, obtain crude product, use silica gel chromatography to crude product purification, obtain PFPA, get 2.38g PFPA solution and 32.84mg azobisisobutyronitrile and 26.34mg4-cyano-4-(sulfur Benzoyl) valeric acid was mixed, the above reaction solution was freeze-thawed three times, and the reactant was placed in an...

technical field

[0001] The invention relates to an amphiphilic polymer fluorescent material and a synthesis method thereof, in particular to a preparation method of a fluorescent dye and a water-soluble near-infrared fluorescent material with high fluorescence quantum yield and which can be used for biological imaging, belonging to chemical synthesis technology field. Background technique

[0002] Fluorescent materials that achieve the purpose of detection or imaging by marking biomolecules or cells are called fluorescent probe materials. Organic fluorescent materials have the advantages of flexible and diverse structures, adjustable luminescence position and intensity, and easy modification. They have become the preferred objects of fluorescent probe materials and have been widely studied. Organic aromatic fluorescent molecules usually show good fluorescence properties, but because most molecules have poor water solubility, it is particularly important to seek a simple and...

Examples

Embodiment 1

[0047] In this example, based on the methods of step 1 and step 2 of the present invention, alfa-amino polyethylene glycol with a chain length of 3 was used to synthesize and prepare the target molecule.

[0048] figure 1 The present invention relates to a synthetic route of PAF-G in an amphiphilic polymer fluorescent material and a synthetic method thereof.

[0049] In a round-bottomed flask, dissolve 2.5g of pentafluorophenol and 1.46g of 2,6-lutidine in dichloromethane, add 1.23g of acryloyl chloride to the mixture in an ice-water bath, and stir the reaction in an ice-water bath 3 hours, remove the ice-water bath and react at room temperature for 12 hours to obtain the crude product, filter with suction, save the filtrate, extract the filtrate with water twice, and use anhydrous MgSO 4 Carry out drying, remove solvent under reduced pressure, obtain crude product, use silica gel chromatography to crude product purification, obtain pentafluorophenol acryloyl chloride (PFPA),...

Embodiment 2

[0051] In this example, based on the methods of step 1 and step 2 of the present invention, alfa-amino polyethylene glycol with a chain length of 5 was used to synthesize and prepare the target molecule.

[0052] In a round-bottomed flask, dissolve 2.5g of pentafluorophenol and 2.91g of 2,6-lutidine in dichloromethane, add 3.69g of acryloyl chloride to the mixture in an ice-water bath, and stir the reaction in an ice-water bath After 5 hours, remove the ice-water bath and react at room temperature for 24 hours to obtain the crude product, filter it with suction, save the filtrate, extract the filtrate twice with water, and use anhydrous MgSO 4 Carry out drying, remove solvent under reduced pressure, obtain crude product, use silica gel chromatography to crude product purification, obtain PFPA, get 2.38g PFPA solution and 16.42mg azobisisobutyronitrile and 5.27mg4-cyano-4-(sulfur Benzoyl) valeric acid was mixed, the above reaction solution was freeze-thawed three times, and the...

Embodiment 3

[0055] In this example, based on the methods of step 1 and step 2 of the present invention, alfa-amino polyethylene glycol with a chain length of 9 was used to synthesize and prepare the target molecule.

[0056] In a round-bottomed flask, dissolve 2.5g of pentafluorophenol and 4.37g of 2,6-lutidine in dichloromethane, add 6.15g of acryloyl chloride to the above mixture, stir and react in an ice-water bath for 10 hours, remove React in an ice-water bath at room temperature for 48 hours to obtain a crude product, filter it with suction, save the filtrate, extract the filtrate twice with water, and use anhydrous MgSO 4 Carry out drying, remove solvent under reduced pressure, obtain crude product, use silica gel chromatography to crude product purification, obtain PFPA, get 2.38g PFPA solution and 32.84mg azobisisobutyronitrile and 26.34mg4-cyano-4-(sulfur Benzoyl) valeric acid was mixed, the above reaction solution was freeze-thawed three times, and the reactant was placed in an...

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