Long-chain azobenzene compound, preparation method and applications thereof

A technology for azobenzene and compounds, which is applied in the field of long-chain azobenzene compounds and their preparation, can solve the problems of short recovery half-life and limited practical application, and achieve the effects of long recovery half-life, simple preparation and great application prospects

Pending Publication Date: 2020-01-03
GUANGDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the traditional azobenzene molecule has problems such as short recovery half-life, which limits its application.
[0003] In the existing technology, the traditional azobenzene molecule has a short recovery half-life technical defect, which limits its practical application in the field of optical switches and optical energy storage.

Method used

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  • Long-chain azobenzene compound, preparation method and applications thereof
  • Long-chain azobenzene compound, preparation method and applications thereof
  • Long-chain azobenzene compound, preparation method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] (1) Preparation of azobenzene derivatives: diazonium reaction of aminobenzene to generate diazonium salt, then coupling reaction with phenol, and filtration and recrystallization to obtain 4-(phenylazo)phenol.

[0037] (2) 0.457g (2mmol) myristic acid was dissolved in 5mL dichloromethane, 0.256mL oxalyl chloride (3mmol) was added dropwise at room temperature and stirred for 10min. A drop of N,N-dimethylformamide was added to the mixture, the solution was stirred for 3 h, and dried to obtain myristyl chloride.

[0038] (3) Dissolve 0.494g tetradecanoyl chloride (2mmol) in 5mL dichloromethane, then add dropwise to 40mL dichloromethane containing 0.595g 4-(phenylazo)phenol (3mmol), 1.1mL (8mmol) triethylamine In methane solution, the mixture was stirred for 12h. The evaporation volume was reduced to 5 mL, and 20 mL of methanol was added to the reaction mixture to obtain a yellow precipitate, which was filtered and washed with methanol to obtain a long-chain azobenzene com...

Embodiment 2

[0042] (1) Preparation of azobenzene derivatives: diazonium reaction of aminobenzene to generate diazonium salt, then coupling reaction with phenol, and filtration and recrystallization to obtain 4-(phenylazo)phenol.

[0043] (2) 0.457g (2mmol) myristic acid was dissolved in 5mL dichloromethane, 0.256mL oxalyl chloride (3mmol) was added dropwise at room temperature and stirred for 10min. A drop of N,N-dimethylformamide was added to the mixture, the solution was stirred for 3 h, and dried to obtain myristyl chloride.

[0044] (3) Dissolve 0.494g myristyl chloride (2mmol) in 5mL dichloromethane, then add dropwise to 40mL dichloromethane containing 0.595g 4-(phenylazo)phenol (3mmol), 1.4mL (10mmol) triethylamine In methane solution, the mixture was stirred for 12h. The evaporation volume was reduced to 5 mL, and 20 mL of methanol was added to the reaction mixture to obtain a yellow precipitate, which was filtered and washed with methanol to obtain a long-chain azobenzene compoun...

Embodiment 3

[0046] (1) Preparation of azobenzene derivatives: diazonium reaction of aminobenzene to generate diazonium salt, then coupling reaction with phenol, and filtration and recrystallization to obtain 4-(phenylazo)phenol.

[0047] (2) 0.457g (2mmol) myristic acid was dissolved in 5mL dichloromethane, 0.218mL thionyl chloride (3mmol) was added dropwise at room temperature and stirred for 10min. A drop of N,N-dimethylformamide was added to the mixture, the solution was stirred for 3 h, and dried to obtain myristyl chloride.

[0048] (3) Dissolve 0.494g tetradecanoyl chloride (2mmol) in 5mL dichloromethane, then add dropwise to 40mL dichloromethane containing 0.595g 4-(phenylazo)phenol (3mmol), 1.1mL (8mmol) triethylamine In methane solution, the mixture was stirred for 12h. The evaporation volume was reduced to 5 mL, and 20 mL of methanol was added to the reaction mixture to obtain a yellow precipitate, which was filtered and washed with methanol to obtain a long-chain azobenzene co...

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PUM

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Abstract

The invention discloses a long-chain azobenzene compound, a preparation method and applications thereof, wherein the structure of the compound is represented by a formula (I), and n is an integer of 10-14. According to the invention, the compound has controllable light responsiveness, can achieve trans-to-cis conversion under the irradiation of ultraviolet light (365+ / -15 nm), can achieve reverseconversion under the irradiation of blue light (450+ / -15 nm), is long in recovery half-life period, is superior to the existing photo-responsive compounds, can be prepared into photoswitches and photothermal fuel materials for application, and has huge application prospects in the field of light-operated medium-and-long-term novel materials; and the preparartion method is simple, does not need harsh conditions, and is suitable for large scale production.

Description

technical field [0001] The invention relates to the technical field of material engineering, more specifically, to a long-chain azobenzene compound, a preparation method and application thereof. Background technique [0002] Azobenzene is composed of two benzene rings connected by a -N=N- group, and has two isomers, trans and cis, and the two isomers can be transformed into each other under the stimulation of external conditions such as light and heat. Photoisomerization properties. Substituting the hydrogen on the azobenzene biphenyl ring, which has different recovery half-lives. Because of the photoisomerization characteristics and structural diversity of azobenzene derivatives, they have potential applications in the fields of optical switches and optical energy storage. However, the traditional azobenzene molecule has problems such as short recovery half-life, which limits its application. [0003] In the prior art, the traditional azobenzene molecule has a short reco...

Claims

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Application Information

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IPC IPC(8): C07C245/08
CPCC07C245/08C07B2200/09
Inventor 江艳黄金全小倩罗文
Owner GUANGDONG UNIV OF TECH
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