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Method for Synthesizing Linear Polyacetylenes Substituted by Different Side Groups by Heck Coupling Reaction

A technology of coupling reaction and polyacetylene, which is applied in the field of polyacetylene synthesis, can solve the problems of reaction substrate restriction, hindering the preparation of structurally functional polyacetylene, and harsh polymerization conditions.

Active Publication Date: 2022-05-20
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the harsh polymerization conditions and reaction substrates of these traditional methods, the preparation of structurally functionalized polyacetylenes is greatly restricted and hindered.

Method used

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  • Method for Synthesizing Linear Polyacetylenes Substituted by Different Side Groups by Heck Coupling Reaction
  • Method for Synthesizing Linear Polyacetylenes Substituted by Different Side Groups by Heck Coupling Reaction
  • Method for Synthesizing Linear Polyacetylenes Substituted by Different Side Groups by Heck Coupling Reaction

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] The materials used are: 1.2 parts of palladium acetate, 3 parts of p-tricresylphosphine, 200 parts of potassium carbonate, 100 parts of 3',5'-dihexyloxy-α-bromostyrene monomer (M1), solvent Toluene (p-Xylene) 500 parts.

[0026] The structural formula of monomer M1 and the synthetic route of polymer Poly(M1)PA are:

[0027]

[0028] The synthetic steps of the polymer are:

[0029] (1) Dissolve 100 parts of 3',5'-dihexyloxy-α-bromostyrene monomer in 500 parts of p-xylene solvent and stir to obtain a monomer solution for use;

[0030] (2) Put 1.2 parts of palladium acetate, 3 parts of ligand, and 200 parts of alkali in a two-neck bottle, then add (1) monomer solution, and pass through Ar after three degassing freeze-thaw cycles 2 Gas protection, and placed in an oil bath, gradually heated to 110 ° C under stirring conditions for polymerization for 24 hours;

[0031] (3) Separation and purification of polyacetylene products: Pour the reaction liquid obtained in step ...

Embodiment 2

[0034] The materials used are: 2 parts of palladium acetate, 5 parts of p-tricresylphosphine, 300 parts of cesium carbonate, 100 parts of 4-formonitrile-α-bromostyrene monomer (M2), and 400 parts of solvent toluene.

[0035] The structural formula of the monomer M2 and the synthesis route of the polymer Poly(M2)PA are:

[0036]

[0037] The synthetic steps of the polymer are:

[0038] (1) Dissolve 100 parts of 4-carbonitrile-α-bromostyrene monomer in 400 parts of p-xylene solvent and stir to obtain a monomer solution for use;

[0039] (2) Put 2 parts of palladium acetate, 5 parts of ligand, and 300 parts of alkali in a two-neck bottle, then add (1) monomer solution, and pass through Ar after three degassing freeze-thaw cycles 2 Gas protection, and placed in an oil bath, gradually heated to 100 ° C under stirring conditions for polymerization for 20 hours;

[0040] (3) Separation and purification of polyacetylene products: Pour the reaction solution obtained in step (2) in...

Embodiment 3

[0043] The materials used are: 1.8 parts of palladium acetate, 4 parts of p-tricresylphosphine, 280 parts of potassium carbonate, 100 parts of 3',5'-dibianoxy-α-bromostyrene monomer (M5), solvent Toluene (p-Xylene) 600 parts.

[0044] The structural formula of monomer M5 and the synthetic route of polymer Poly(M5)PA are:

[0045]

[0046] The synthetic steps of the polymer are:

[0047] (1) Dissolve 100 parts of 3',5'-dibenzyloxy-α-bromostyrene monomer in 600 parts of p-xylene solvent and stir to obtain a monomer solution for use;

[0048] (2) Place 1.8 parts of palladium acetate, 4 parts of ligand, and 280 parts of alkali in a two-necked bottle, then add (1) monomer solution, and pass through Ar after three degassing freeze-thaw cycles 2 Gas protection, and placed in an oil bath, gradually heated to 120 ° C under stirring conditions for polymerization for 18 hours;

[0049] (3) Separation and purification of polyacetylene products: Pour the reaction solution obtained in...

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Abstract

The invention belongs to the technical field of polyacetylene synthesis and preparation, in particular to a method for synthesizing linear polyacetylene substituted by different side groups through Heck coupling reaction. The method of the invention comprises: designing and preparing α-bromostyrene or α-bromovinyl type AB monomers, and then synthesizing the monomers into polyacetylene polymers substituted with different side groups through Heck coupling reactions. The traditional method of synthesizing polyacetylene has harsh polymerization conditions, reaction substrates and other factors, which greatly restrict and hinder the preparation of structurally functionalized polyacetylene. In the present invention, α-bromostyrene or α-bromovinyl type AB monomer is used to synthesize linear polyacetylene through Heck coupling reaction, and the synthesis of linear polyacetylene substituted by different side groups can be easily realized by designing the structure of the monomer . The method of the invention is simple and easy to realize, and provides a new way and a new idea for the synthesis of the functionalized polyacetylene polymer.

Description

technical field [0001] The invention belongs to the technical field of polyacetylene synthesis, in particular to a method for synthesizing linear polyacetylene substituted by different side groups through a Heck coupling reaction. Background technique [0002] Polyacetylene is a semiconductor-type conjugated polymer material. Because polyacetylene has excellent properties such as excellent photoconductivity, energy transfer conversion, electrical conductivity, and paramagnetism, it is widely used in electrochemical sensors, plastic electronics, and electroluminescent materials. , Molecular devices and other fields have important applications. After years of research and development, it has been considered as an important conductive polymer material and has played an important role in the development of the national economy. There are many traditional methods for synthesizing polyacetylene, such as direct synthesis of acetylene compounds, heterotopic polymerization of olefins...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G61/04
CPCC08G61/04C08G2261/11C08G2261/1424C08G2261/3327C08G2261/413C08G2261/143C08G2261/122
Inventor 何军坡何立挺
Owner FUDAN UNIV