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Fluorinated derivative based on azobenzene and preparation method of fluorinated derivative

A technology of azobenzene derivatives and p-aminobenzoic acid, which is applied in the field of azobenzene-based fluorinated derivatives and its preparation, can solve the problems of limiting the application range of azobenzene, easy scattering of ultraviolet rays, and damage to organisms. Achieve the effects of reducing electron cloud density, excellent optical performance, and improving stability

Inactive Publication Date: 2018-11-23
TIANJIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Generally, the photoisomerization process of azobenzene molecules is driven by ultraviolet light, and ultraviolet light has a great pollution to the environment, which limits the application range of azobenzene
For example, in the in situ molecular switch, ultraviolet light is easy to scatter, and it is difficult to penetrate from tissues or cells. In addition, ultraviolet light can also cause damage to the organism itself.

Method used

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  • Fluorinated derivative based on azobenzene and preparation method of fluorinated derivative
  • Fluorinated derivative based on azobenzene and preparation method of fluorinated derivative
  • Fluorinated derivative based on azobenzene and preparation method of fluorinated derivative

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Embodiment 1

[0030] 1) Preparation of diazonium salt: 1.37g of 4-aminobenzoic acid (10mmol) and 0.4g of NaOH (10mmol) were weighed and dissolved in 30mL of deionized water, and recorded as A. Weigh 0.76g NaNO 2 (11mmol) was dissolved in 5mL deionized water, and 10mL NaNO 2 Slowly added dropwise to A. After being completely dissolved, the solution was added dropwise to 40mL HCl (1molL -1 ), keep the temperature at 0-5°C, stir and react for 30 minutes to obtain a diazonium salt solution, and store it in an ice bath for later use.

[0031] 2) Coupling reaction: weigh 1.29g of 3,5-difluoroaniline (10mmol) (1:1 molar ratio to diazonium salt) and dissolve in HCl (1mol L -1 ), denoted as B; and the above-mentioned diazonium salt solution was slowly added dropwise to B and stirred.

[0032] 3) Adjust pH: prepare NaHCO 3 Saturated aqueous solution; add the aqueous solution dropwise to the above mixed solution to adjust the pH, and adjust the pH to 5-7; continue to stir for 10 hours under ice b...

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Abstract

The invention discloses a fluorinated derivative based on azobenzene and a preparation method of the fluorinated derivative. An ortho-fluoro substituted azobenzene derivative is prepared by using a diazotization coupling method, two fluorine atoms are introduced at the ortho positions of azobenzene, so that the electron cloud density of nitrogen-nitrogen double bonds is effectively reduced, the red shift of the absorption spectrum of an azobenzene molecule is realized, and the stability of cis-configuration is greatly improved. Synthetizing ortho-fluoro substituted azobenzene through a diazotization coupling reaction is simple and efficient, the yield is relatively high, and the obtained material has excellent optical performance, and is expected to be applied in the fields of optical driving, light energy storage and supramolecular assembly and the like.

Description

technical field [0001] The invention belongs to the field of material technology, and more specifically relates to a fluorinated derivative based on azobenzene and a preparation method thereof, which has broad application prospects in the fields of solar energy storage and optical drive. Background technique [0002] Functional group substitution is an effective means to control the photophysical properties of azobenzene, so designing and synthesizing azobenzene molecules substituted with different functional groups is the basis and key of this field. In past research, a large number of azobenzene molecules were synthesized. For different molecular structures of azobenzene, a large number of synthetic methods have been developed and studied in depth, and a relatively complete theory of azobenzene synthesis has gradually been formed. Different synthetic methods have their advantages as well as limitations. For example, the diazotization coupling reaction is the most commonl...

Claims

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Application Information

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IPC IPC(8): C07C245/08
CPCC07B2200/09C07C245/08C07C245/20
Inventor 封伟董立奇冯奕钰秦承群
Owner TIANJIN UNIV
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