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Polyacetylene amide compound as well as preparation method and application thereof

A polyalkyne amide and compound technology, which is applied in the fields of polymer chemistry and materials science, can solve the problems of difficulty in the preparation of alkynoic acid monomers, limit the preparation and application of polyalkyne amides, etc., and achieves easy availability of catalysts, low cost, and good thermal stability. sexual effect

Active Publication Date: 2021-12-07
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the preparation of alkyne acid monomers is difficult, which limits the preparation and application of polyalkyne amides

Method used

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  • Polyacetylene amide compound as well as preparation method and application thereof
  • Polyacetylene amide compound as well as preparation method and application thereof
  • Polyacetylene amide compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] A polyalkyne amide compound, its structural formula is as shown in P1:

[0049]

[0050] The polyalkyne amide compound is prepared by the polymerization reaction of water, difunctional terminal alkyne monomer and difunctional isonitrile monomer, and the reaction equation is as formula (1):

[0051]

[0052] Among them, the monomer M1 can be synthesized by referring to the preparation method of the literature (ACS Macro Lett., 2019, 8(2): 101-106); the monomer N1 can be synthesized by referring to the literature (Macromolecules, 2021, 54(9): 4112-4119 and J.Am.Chem.Soc., 2018,140(19):6156-6163) synthesis method.

[0053] The preparation steps of described polyalkyne amide compounds are as follows:

[0054]Add anhydrous cobalt bromide (CoBr 2 ) (0.01mmol, 2.2mg), silver nitrate (AgNO 3 ) (0.4mmol, 68mg), bis(2-diphenylphosphophenyl) ether (DPEphos) (0.08mmol, 43.1mg,) and M1 (0.2mmol, 58.6mg), pumped nitrogen three times, under nitrogen atmosphere , injected N1 ...

Embodiment 2

[0057] A kind of polyalkyne amide compound, its structural formula is as shown in P2:

[0058]

[0059] The polyalkyne amide compound is prepared by the polymerization reaction of water, difunctional terminal alkyne monomer and difunctional isonitrile monomer, and the reaction equation is as formula (2):

[0060]

[0061] Wherein, the synthesis method of monomers M1 and N2 is the same as in Example 1.

[0062] The preparation steps of described polyalkyne amide compounds are as follows:

[0063] Add anhydrous CoBr to a 10 mL dry polymerization tube equipped with a magnetic stir bar 2 (0.02mmol, 4.4mg), AgNO 3 (0.4mmol, 68mg), DPEphos (0.08mmol, 43.1mg), M1 (0.2mmol, 58.6mg) and N2 (0.2mmol, 32.8mg), pump nitrogen three times, under nitrogen atmosphere, inject 0.33mL DCE , and finally water (1.4 mmol, 25 μL) was injected, and the reaction system was reacted at 40° C. for 8 hours. After the reaction, cool to room temperature, add 3.5mL DCE, stir and dilute. Then the o...

Embodiment 3

[0066] A kind of polyalkyne amide compound, its structural formula is as shown in P3:

[0067]

[0068] The polyalkyne amide compound is prepared by the polymerization reaction of water, difunctional group terminal alkyne monomer and bifunctional isonitrile monomer, and the reaction equation is as formula (3):

[0069]

[0070] Wherein, the synthesis method of monomers M1 and N3 is the same as in Example 1.

[0071] The preparation steps of described polyalkyne amide compounds are as follows:

[0072] Add anhydrous CoBr to a 10 mL dry polymerization tube equipped with a magnetic stir bar 2 (0.03mmol, 6.6mg), AgNO 3 (0.4mmol, 68mg), DPEphos (0.08mmol, 43.1mg), M1 (0.2mmol, 58.6mg) and N3 (0.2mmol, 46.0mg), pump nitrogen three times, under nitrogen atmosphere, inject 0.25mL DCE and 0.25 mL DMAc, and finally injected water (2.6 mmol, 47 μL), and the reaction system was reacted at 80° C. for 4 hours. After the reaction, cool to room temperature, add 3.5mL of DCE, and sti...

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Abstract

The invention discloses a polyacetylene amide compound as well as a preparation method and application thereof. The preparation method comprises the following steps that: under the inert gas atmosphere, water, a bifunctional terminal alkyne monomer and a bifunctional isonitrile monomer are subjected to a polymerization reaction in an organic solvent under the combined action of a catalyst and a ligand, and after the reaction is finished, the product is purified and dried to obtain the polyacetylene amide compound. The method is mild in condition, and the polymerization monomer is simple and easy to obtain. The polyacetylene amide compound obtained by the method has relatively good solubility and relatively high thermal stability, and has potential application in the field of self-assembly.

Description

technical field [0001] The invention relates to the fields of polymer chemistry and material science, in particular to a polyalkyne amide compound and its preparation method and application. Background technique [0002] Water, a colorless liquid under ambient conditions, covers 71% of the Earth's surface and is essential to life. As one of the ubiquitous substances in nature, water is a double-edged sword in the field of organic synthesis, that is, it can be used as a solvent for some reactions, and it may have adverse effects on the reactions. In the field of polymer chemistry, water often occurs as a by-product or as a quencher to terminate polymerization reactions. Moreover, the catalytic system of many polymerization reactions is very fragile and requires strict anhydrous and oxygen-free conditions. Therefore, rational utilization of water as a monomer to construct polymers faces great challenges. [0003] Since Shirakawa, MacDiarmid and Heeger found that doped polya...

Claims

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Application Information

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IPC IPC(8): C08G69/00
CPCC08G69/00
Inventor 唐本忠刘东明秦安军胡蓉蓉赵祖金王志明
Owner SOUTH CHINA UNIV OF TECH
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