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Azobenzene side chain polymerizable monomer based on modified cis-5-norbornene-2,3-dicarboxylic anhydride and applications thereof

A technology of norbornene and dicarboxylic anhydride, which is applied in the fields of polymer materials and solar energy storage, can solve the problems of low energy density and short half-life of azobenzene, and achieve the effects of high atom utilization rate, easy operation and mild reaction conditions.

Inactive Publication Date: 2020-01-31
TIANJIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, ordinary azobenzene has low energy density and short half-life, so proper molecular design of azobenzene is needed to improve its energy density and half-life

Method used

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  • Azobenzene side chain polymerizable monomer based on modified cis-5-norbornene-2,3-dicarboxylic anhydride and applications thereof
  • Azobenzene side chain polymerizable monomer based on modified cis-5-norbornene-2,3-dicarboxylic anhydride and applications thereof
  • Azobenzene side chain polymerizable monomer based on modified cis-5-norbornene-2,3-dicarboxylic anhydride and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] 1) The preparation of azobenzene (AZO) monomer is based on the mole of tricarboxyaniline, equivalent, 1.5 equivalents, 3 equivalents, and 4 equivalents are one time, 1.5 times, 3 times and 4 times of tricarboxyaniline.

[0040] ① 20mmol tricarboxyaniline was added to the aqueous solution in which 3 equivalents of sodium hydroxide were dissolved.

[0041] ②Dissolve an equivalent amount of sodium nitrite in water, and then add this solution dropwise to the solution in ① at 0°C under stirring conditions. After completely dissolving, add 4 equivalents of 1mol / L hydrochloric acid (that is, aqueous hydrogen chloride solution), Stirring was continued for 2 hours.

[0042] ③Under the protection of argon, 1.5 equivalents of 3,5-dimethoxyaniline was added to the solution of ②, stirred and reacted in ice bath for 5 hours, and AZO monomer was obtained.

[0043] 2) Preparation of polymer composites containing azo side chains:

[0044] ①Dissolve 20mmol of 6-amino-hexanol in concent...

Embodiment 2

[0048] 1) The preparation of AZO monomer, based on the mole of tricarboxyaniline, equivalent, 1.5 equivalent, 3 equivalent, 4 equivalent is one time, 1.5 times, 3 times and 4 times of tricarboxyaniline.

[0049] ① 25mmol of tricarboxyaniline was added to the aqueous solution in which 3 equivalents of sodium hydroxide were dissolved.

[0050] ②Dissolve an equivalent amount of sodium nitrite in water, and then add this solution dropwise to the solution in ① at 0°C under stirring conditions. After completely dissolving, add 4 equivalents of 1mol / L hydrochloric acid solution and continue stirring for 2 Hour

[0051] ③Under the protection of argon, 1.5 equivalents of 3,5-dimethoxyaniline was added to the solution of ②, stirred and reacted in ice bath for 5 hours, and AZO monomer was obtained.

[0052] 2) Preparation of polymer composites containing azo side chains:

[0053] 20 mmol of 6-amino-hexanol was dissolved in concentrated hydrobromic acid (purity: 48%, that is, the mass p...

Embodiment 3

[0057] 1) The preparation of AZO monomer, based on the mole of tricarboxyaniline, equivalent, 1.5 equivalent, 3 equivalent, 4 equivalent is one time, 1.5 times, 3 times and 4 times of tricarboxyaniline.

[0058] ①30mmol of tricarboxyaniline was added to the aqueous solution in which 3 equivalents of sodium hydroxide were dissolved.

[0059] ②Dissolve an equivalent amount of sodium nitrite in water, and then add this solution dropwise to the solution in ① at 0°C under stirring conditions. After completely dissolving, add 4 equivalents of 1mol / L hydrochloric acid solution and continue stirring for 2 Hour

[0060] ③Under the protection of argon, 1.5 equivalents of 3,5-dimethoxyaniline was added to the solution of ②, stirred and reacted in ice bath for 5 hours, and AZO monomer was obtained.

[0061] 2) Preparation of polymer composites containing azo side chains:

[0062] 30 mmol of 6-amino-hexanol was dissolved in concentrated hydrobromic acid (purity: 48%, that is, the mass pe...

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Abstract

The invention discloses an azobenzene side chain polymerizable monomer based on modified cis-5-norbornene-2,3-dicarboxylic anhydride and applications thereof, wherein a polymerizable monomer is obtained by grafting synthesized azobenzene to norbornene anhydride, polyhydroxy azobenzene as a side chain is linked to the main chain of the norbornene anhydride, and the storage and the release of polymer energy are achieved through intermolecular hydrogen bonding force and cis-trans isomerization of azobenzene. According to the invention, the target polymer is obtained through ring-opening metathesis polymerization; and compared with the common azobenzene molecules, the obtained azobenzene side chain-containing polymer material of the invention has advantages of substantially improved energy density, substantially improved half-life period and good plasticity, so that the new method is provided for solar energy utilization, and the application range of azobenzene polymers is widened.

Description

technical field [0001] The invention belongs to the field of macromolecular materials, and more specifically relates to azobenzene side chain polymerizable monomers based on modified cis-5-norbornene-2,3-dicarboxylic anhydride and its application and plasticity An azobenzene polymer energy storage material and a preparation method thereof have broad application prospects in the field of solar energy storage. Background technique [0002] With the rapid development of the world economy, the rapid improvement of science and technology, the demand for existing energy is also increasing, such as coal, oil, natural gas and other fossil resources. However, these resources are increasingly scarce, and human beings are exploiting these resources. Many environmental problems, such as the greenhouse effect, smog and other problems, have caused serious threats to the good life of human beings and the sustainable development of society. Therefore, the development and utilization of gre...

Claims

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Application Information

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IPC IPC(8): C07D209/56C08G61/08
CPCC07D209/56C08G61/08C08G2261/11C08G2261/143C08G2261/334C08G2261/418
Inventor 封伟刘浩符林霞冯奕钰
Owner TIANJIN UNIV
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