Ortho-fluoro-azobenzene derivative and preparation method thereof

An azobenzene derivative and ortho-position technology is applied in the field of preparation of ortho-fluorinated azobenzene, which can solve the problems of limiting the application range of azobenzene, easy scattering of ultraviolet rays, biological damage, etc., so as to prolong the recovery half-life, Excellent optical performance, the effect of 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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  • Ortho-fluoro-azobenzene derivative and preparation method thereof
  • Ortho-fluoro-azobenzene derivative and preparation method thereof
  • Ortho-fluoro-azobenzene derivative and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] 1) Preparation of diazonium salt: 1.55g of 4-amino-3-fluorobenzoic acid (10mmol) and 0.4g of NaOH (10mmol) were weighed, dissolved in 30mL of deionized water, and recorded as A. Weigh 0.76g NaNO 2 (11mmol) was dissolved in 10mL deionized water, and 10mL NaNO 2 Slowly added dropwise to A. After being completely dissolved, the solution was added dropwise to 40mL HCl (1mol L -1 ), keep the temperature at 0-5°C, stir and react for 60 minutes to obtain a diazonium salt solution, and store in an ice bath.

[0032] 2) Coupling reaction: weigh 1.11g 3-fluoroaniline (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.

[0033] 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 5 hours under ice bath conditions, a...

Embodiment 2

[0036] 1) Preparation of diazonium salt: 3.1 g of 4-amino-3-fluorobenzoic acid (20 mmol) and 0.8 g of NaOH (20 mmol) were weighed, dissolved in 100 mL of deionized water, and recorded as A. Weigh 1.52g NaNO 2 (22mmol) was dissolved in 20mL deionized water, and 20mL NaNO 2 Slowly added dropwise to A. After being completely dissolved, the solution was added dropwise to 80mL HCl (1mol L -1 ), keep the temperature at 0-5°C, stir and react for 60 minutes to obtain a diazonium salt solution, and store in an ice bath.

[0037] 2) Coupling reaction: Weigh 2.22g of 3-fluoroaniline (20mmol) (the molar ratio of diazonium salt is 1:1) and dissolve it in HCl, denoted as B; slowly add the above diazonium salt solution dropwise Stir in B.

[0038] 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 8 hours under ice bath conditions, and filter under reduced ...

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PUM

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Abstract

The invention discloses an ortho-fluoro-azobenzene derivative and a preparation method thereof. The ortho-fluoro-substituted azobenzene derivative is prepared by a diazotization coupling method; two fluorine atoms are introduced into the ortho-position of azobenzene, so that the electronic cloud density of nitrogen-nitrogen double bonds can be effectively reduced; the red shifting of azobenzene molecular absorption spectroscopy can be realized; the stability performance of a cis-configuration is greatly improved. The method of synthesizing the ortho-fluoro-azobenzene through diazotization coupling reaction is simple and efficient; the yield is high; the obtained material has excellent optical performance, and is hopeful to be applied in the fields of light driving, light energy storage, supramolecular assembly and the like.

Description

technical field [0001] The invention relates to the preparation of an ortho-fluoroazobenzene, which has broad application prospects in the fields of solar energy storage and light 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 commonly used method for the synthesis of azobenzene molecules. The reaction is mainly through the diazotiza...

Claims

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Application Information

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Patent Type & Authority Applications(China)
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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