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Anion coordination self-assembly supramolecular gel synthesis method and application

A supramolecular gel, self-assembly technology, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve the problems of large external influence, large radius, low charge density, etc.

Active Publication Date: 2022-02-11
NORTHWEST UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, as anion complementary to metal cations, it has only received extensive attention in recent years. Although anion coordination was discovered by chemists at the same time as metal cation coordination, due to the characteristics of anion itself, such as large radius, complex structure, and low charge density , The form of existence is greatly affected by external factors, etc. Anion coordination chemistry has been developing very slowly (Zhao, J. et al. Anion coordination chemistry: From recognition to supramolecular assembly, Coord. Chem. Rev. 2019, 378, 415-444.)

Method used

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  • Anion coordination self-assembly supramolecular gel synthesis method and application
  • Anion coordination self-assembly supramolecular gel synthesis method and application
  • Anion coordination self-assembly supramolecular gel synthesis method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Synthesis and characterization of compound b:

[0041] Will (Boc) 2O (0.75g, 3.4mmol) tetrahydrofuran solution was slowly added dropwise to compound a (1g, 3.4mmol) in tetrahydrofuran solution (20mL), and reacted overnight in ice bath. After the reaction, the product was separated by silica gel column chromatography (eluent: petroleum ether: ethyl acetate = 1:1), and the product was collected and rotary evaporated to obtain product b as a light pink solid with a yield of 50%. 1 H NMR (400MHz, DMSO-d 6 ,ppm): δ8.99(s,1H,Hb),7.14(d,J=8Hz,2H,H4),6.69(d,J=8Hz,4H,H1),6.58(d,J=8Hz,2H ,H3),6.48(d,J=8Hz,4H,H2),4.87(s,4H,Ha),1.44(s,9H,H5). 13 C NMR (100MHz, DMSO-d 6 , ppm): δ153.0, 144.7, 137.0, 131.2, 126.1, 119.5, 119.1, 114.8, 78.5, 28.2. ESI-MS m / z, found 390.2010, calcd for C 23 h 26 N 4 o 2 [M+H] + 391.2129.

Embodiment 2

[0043] Synthesis and characterization of compound c:

[0044] Compound b (0.5g, 1.28mmol) and o-nitrophenylisocyanate (0.46g, 2.81mmol) were dissolved in 5mL of tetrahydrofuran and added to a 50mL three-necked flask, heated and stirred at 50°C, the solution gradually turned dark red orange, Three hours later, the plate detection reaction was completed. The reaction liquid was rotary evaporated to about 2 mL, and diethyl ether was added to precipitate an orange-red solid compound c, which was filtered and dried with a yield of 98%. 1 H NMR (400MHz, DMSO-d 6 ,ppm): δ9.77(s,2H,Hb),9.57(s,2H,Ha),9.26(s,1H,Hc),8.31(d,J=8Hz,2H,H3),8.08(d, J=8Hz, 2H, H6), 7.69(t, J=8Hz, 2H, H4), 7.40(d, J=8Hz, 6H, H2), 7.19(t, J=8Hz, 2H, H5), 6.93( d,J=8Hz,6H,H1),1.47(s,9H,H7). 13 C NMR (100MHz, DMSO-d 6 , ppm): δ152.8, 151.8, 142.6, 141.9, 137.4, 135.1, 135.0, 134.6, 133.8, 125.4, 124.2, 123.5, 122.4, 122.0, 120.0, 119.6, 78.8, 28.1. ESI-MS m / z.22 957 calcd for C 37 h 34 N 8 o 8 [M+H] + 7...

Embodiment 3

[0046] Synthesis and characterization of compound d:

[0047] Add 3mL of hydrazine hydrate dropwise into 20mL of ethanol suspension containing compound c (0.7g, 1mmol) and Pd / C (70mg), react at 50°C for 5min, and wait for the orange-red particles in the solution to disappear, spot plate detection The reaction is over. The Pd / C was filtered out with diatomaceous earth, and the obtained filtrate was subjected to rotary evaporation, leaving a small amount of mother liquor, adding water to precipitate a white solid d, and the yield was 92%. 1 H NMR (400MHz, DMSO-d 6 ,ppm): δ9.22(s,H,Hd),8.65(s,2H,Hb),7.66(s,2H,Ha),7.32(d,J=8Hz,8H,H2 / H3),6.89( d,J=8Hz,6H,H1),6.83(t,J=8Hz,2H,H5),6.74(d,J=8Hz,2H,H6),6.26(t,J=8Hz,2H,H4), 4.75(s,4H,Hc),1.46(s,9H,H7). 13 C NMR (100MHz, DMSO-d 6 , ppm): δ153.2, 152.9, 142.3, 141.8, 140.8, 134.9, 134.2, 124.9, 124.3, 123.8, 123.6, 123.5, 119.4, 116.9, 115.9, 78.8, 28.2. ESI-MS m / z, found 697.28 for 02, C 37 h 38 N 8 o 4 [M+H] + 697.2648.

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Abstract

The invention provides a series of triple helical structures based on phosphate anion coordination aiming at the current situation that the application of a currently reported supramolecular cage structure constructed by anion coordination is deficient. The supramolecular structures are connected by virtue of covalent bonds through post-modification, so that a series of supramolecular gel materials with adhesion property are obtained.

Description

technical field [0001] The invention relates to the field of supramolecular gel synthesis, in particular to an anion coordination self-assembly supramolecular gel synthesis method and its application. Background technique [0002] In recent years, the demand for strong, stretchable and self-healing materials has been increasing in fields such as electronic skin, wearable electronics and artificial muscles. The self-healing performance of polymer material damage can be achieved by introducing reversible dynamic covalent bonds into polymer materials, but the strength of self-healing materials prepared with a single non-covalent bond is low, especially self-healing hydrogels and elastomers, Its strength is usually weak. Therefore, how to obtain flexible composites with high tensile properties, excellent mechanical strength, and high self-healing ability has been a long-standing challenge. [0003] Supramolecular polymer gel is a very important soft matter material, which repr...

Claims

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Application Information

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IPC IPC(8): C08G83/00C07C273/18C07C275/40
CPCC08G83/008C07C273/1854C07C275/40
Inventor 杨栋赵捷吴彪杨晓娟
Owner NORTHWEST UNIV
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