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Visible-light-responsive aryl azo pyrazole polymer and synthesis method thereof

A technology of aryl azopyrazole and synthesis method, which is applied in the field of light-responsive functional polymers, can solve problems such as limiting the functions of light-responsive polymers, and achieve the effects of simple synthesis process, high degree of isomerization, and rapid recovery

Active Publication Date: 2021-05-25
UNIV OF SCI & TECH BEIJING
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the currently reported azobenzene derivatives are usually limited to complete isomerization from trans to cis under ultraviolet light irradiation, and the degree of isomerization and half-life of azobenzene need to be improved, which greatly limits the Wider applications of light-responsive polymer functions

Method used

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  • Visible-light-responsive aryl azo pyrazole polymer and synthesis method thereof
  • Visible-light-responsive aryl azo pyrazole polymer and synthesis method thereof
  • Visible-light-responsive aryl azo pyrazole polymer and synthesis method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] 1) 4-(Methylthio)aniline (2.78 g, 20 mmol) was dissolved in a mixed solution of concentrated hydrochloric acid (12 M, 0.5 mL) and 2 mL of ethanol and cooled to 0°C. 2 mL of sodium nitrite (1.7 g, 24 mmol) aqueous solution was slowly added dropwise to the above solution and stirred for 1 h to prepare the diazonium salt. Acetylacetone (2.6 g, 26 mmol) was added to 50% ethanol in water followed by sodium acetate (4.92 g, 60 mmol) and cooled. The above diazonium salt solution was slowly added dropwise to the solution and the reaction was stirred, and the obtained yellow precipitate was filtered and washed with 200 mL of an aqueous solution containing 50% ethanol to obtain a yellow crude arylazoacetylacetone. Arylazoacetylacetone (2.5 g, 10 mmol) was dissolved in 50 mL of ethanol, then hydrazine hydrate (0.6 g, 12 mmol) was added dropwise to it, and the mixed liquid was stirred and heated to 70° C. and refluxed for 24 h under nitrogen atmosphere. After the reaction was comp...

Embodiment 2

[0034] 1) 4-(Methylthio)aniline (1.36 g, 10 mmol) was dissolved in a mixed solution of concentrated hydrochloric acid (12 M, 0.4 mL) and 3 mL of ethanol and cooled to 0°C. 1 mL of sodium nitrite (1.2 g, 17 mmol) aqueous solution was slowly added dropwise to the above solution and stirred for 1.5 h to prepare the diazonium salt. Acetylacetone (2 g, 20 mmol) was added to 70% ethanol in water followed by sodium acetate (4 g, 49 mmol) and cooled. The above diazonium salt solution was slowly added dropwise to the solution and the reaction was stirred. The obtained yellow precipitate was filtered and washed with 200 mL of an aqueous solution containing 70% ethanol to obtain a yellow crude product of arylazoacetylacetone. Arylazoacetylacetone (1 g, 4 mmol) was dissolved in 20 mL of ethanol, then hydrazine hydrate (0.5 g, 10 mmol) was added dropwise thereto, and the mixed liquid was stirred and heated to 80° C. and refluxed for 18 h under nitrogen atmosphere. After the reaction was c...

Embodiment 3

[0038] 1) 4-(Methylthio)aniline (5 g, 36 mmol) was dissolved in a mixed solution of concentrated hydrochloric acid (12 M, 2 mL) and 10 mL of ethanol and cooled to 0°C. 5 mL of sodium nitrite (6.9 g, 100 mmol) aqueous solution was slowly added dropwise to the above solution and stirred for 2 h to prepare the diazonium salt. Acetylacetone (10 g, 100 mmol) was added to 80% ethanol in water followed by sodium acetate (10 g, 122 mmol) and cooled. The above diazonium salt solution was slowly added dropwise to the solution and the reaction was stirred. The obtained yellow precipitate was filtered and washed with 300 mL of an aqueous solution containing 80% ethanol to obtain a yellow crude product of arylazoacetylacetone. Arylazoacetylacetone (4 g, 16 mmol) was dissolved in 60 mL of ethanol, then hydrazine hydrate (4 g, 80 mmol) was added dropwise to it, and the mixed liquid was stirred and heated to 80° C. and refluxed for 48 h under nitrogen atmosphere. After the reaction was compl...

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Abstract

The invention relates to a visible-light-responsive aryl azo pyrazole polymer and a synthesis method thereof. The aryl azo pyrazole polymer is prepared from a methylthio para-substituted aryl azo pyrazole derivative and a polyamide-amine (PAMAM) dendritic macromolecule through a Michael addition reaction. The methylthio para-substituted aryl azo pyrazole in the aryl azo pyrazole polymer is prepared through a standard diazotization reaction, and the trans-to-cis-isomer conversion and the cis-to-trans recovery process of the aryl azo pyrazole can be completed under the excitation of visible light. The synthesis method is simple, the yield is high, the azo pyrazole functional group in the aryl azo pyrazole polymer can achieve the high isomerization degree from trans to cis under the irradiation of purple light (405 nm), and rapid recovery from cis to trans can be achieved under the irradiation of green light (520 nm). In addition, the half-life period of the cis-isomer is as long as 13 days under room-temperature dark conditions. The method disclosed by the invention opens up a new way for developing novel visible light response functional polymer materials and molecular photo-thermal storage materials.

Description

technical field [0001] The invention belongs to the field of light-responsive functional polymers, in particular to a visible light-responsive arylazopyrazole polymer and a synthesis method. Background technique [0002] Azobenzene compounds are photochromic molecules, which generally undergo trans-to-cis isomerization under UV light irradiation and cis-to-trans reversion under green light irradiation. Based on reversible photoisomerization, many researchers at home and abroad have reported many researches on grafting azobenzene into polymerization to prepare light-responsive functional polymers. emerging in a variety of technical fields. However, currently reported azobenzene derivatives are usually limited to complete trans-to-cis isomerization under UV light irradiation, and the degree of isomerization and half-life of azobenzene need to be improved. Light-responsive macromolecules have a wider range of applications. To address this scientific challenge, a pyrazolylazo...

Claims

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Application Information

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IPC IPC(8): C08G83/00C08G73/02
CPCC08G83/004C08G73/028
Inventor 王国杰徐兴堂
Owner UNIV OF SCI & TECH BEIJING
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