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Quick-response reversible-photoisomerization perfluorinated-ether-chain azobenzene and preparation method therefor

A perfluoroether chain azobenzene, photoisomerization technology, applied in chemical instruments and methods, color-changing fluorescent materials, organic chemistry, etc., can solve the problem of slow light response speed and light response degree of photochromic azobenzene compounds Weak and other problems, to achieve the effect of rapid, complete and reversible response, and a wide range of applications

Inactive Publication Date: 2015-09-23
DONGHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] What the present invention aims to solve is the problem of slow photoresponse speed or weak photoresponse degree of existing photochromic azobenzene compounds and environmental protection problems of fluorine-containing azobenzene compounds

Method used

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  • Quick-response reversible-photoisomerization perfluorinated-ether-chain azobenzene and preparation method therefor
  • Quick-response reversible-photoisomerization perfluorinated-ether-chain azobenzene and preparation method therefor
  • Quick-response reversible-photoisomerization perfluorinated-ether-chain azobenzene and preparation method therefor

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] (1) The three-necked flask equipped with a reflux device was subjected to anhydrous treatment, and under ice bath conditions (0-5°C), a mixture of p-phenylenediamine (2.16g, 20mmol) and triethylamine (4mL, 30mmol) was added 60 mL of tetrahydrofuran solution was stirred with magnetic force for 30 min, then perfluoroether fluoride was added dropwise, and added dropwise for 2 hours until the reaction was complete. After the reaction, the reaction was quenched with water, and the organic phase was spin-dried under reduced pressure, and purified by column chromatography to obtain (4-perfluoroetheramide) aniline (R f , n=1, compound a) 3.26g (white solid, yield 55.6%). Its NMR spectrum is as Figure 1a , 1b shown.

[0033] (2) Add 30mL of 2M hydrochloric acid solution dropwise to compound a (1.172g, 2mmol) under ice bath conditions (0-5°C), dissolve under magnetic stirring conditions, and slowly add 30% of Sodium nitrate solution 0.51g, continue to react for 0.5h. Slowly ...

Embodiment 2

[0036] (1) The three-necked flask equipped with a reflux device was subjected to anhydrous treatment, and at room temperature, 30 mL of a dichloromethane solution of p-phenylenediamine (1.08 g, 10 mmol) and triethylamine (2 mL, 15 mmol) was added, and magnetically After stirring for 30 minutes, perfluoroether-acyl fluoride was added dropwise, and added dropwise for 2 hours until the reaction was complete. After the reaction, the reaction was quenched with water, the organic phase was spin-dried under reduced pressure, and purified by column chromatography to obtain 1.54 g of compound a (white solid, yield 52.6%).

[0037] (2) Add 30mL of 2M hydrochloric acid solution dropwise to compound a (5.86g, 10mmol) under ice bath conditions (0-5°C), dissolve under magnetic stirring conditions, and slowly add 30% of Sodium nitrate solution 2.8g, continue to react for 0.5h. Slowly add a solution of phenol (1.41g, 15mmol) in sodium hydroxide (0.8g, 20mmol) and sodium carbonate (1.48g, 14m...

Embodiment 3

[0039] Example 3: Compound c transforms from trans to cis under UV light irradiation

[0040] Compound c was dissolved in tetrahydrofuran to prepare 5 × 10 -5 mol / L solution, under the irradiation of 365nm ultraviolet light, record the ultraviolet spectrogram every 30s, and draw the absorbance-wavelength relationship graph at different time of ultraviolet light irradiation, such as Figure 4 shown. Figure 4 It shows that compound c rapidly undergoes trans-cis isomerization under the irradiation of 365nm ultraviolet light, and after continuous irradiation for about 120s, the spectrogram no longer changes significantly, and reaches a photostable state, completely converting from trans to cis.

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Abstract

The invention discloses quick-response reversible-photoisomerization perfluorinated-ether-chain azobenzene and a preparation method therefor. The perfluorinated-ether-chain azobenzene has a structural formula shown in the description. The preparation method comprises the steps: dissolving p-phenylene diamine and perfluoroether acyl fluoride, which serve as starting compounds, in an organic solvent so as to prepare (4-perfluoroether amide)phenylamine; diazotizing the compound by a hydrochloride / nitrite system, and then, enabling the diazotized compound to react with an alkali solution of phenol so as to prepare 4-perfluoroether amide-4'-hydroxyazobenzene; and in an anhydrous organic solvent, enabling 4-perfluoroether amide-4'-hydroxyazobenzene to react with methacryloyl chloride or acryloyl chloride so as to prepare 4-perfluoroether amide-4'-methacrylate azobenzene or 4-perfluoroether amide-4'-acrylate azobenzene. The compound disclosed by the invention has the advantages of reversible photoisomerization, quick response and high isomerization degree; a fluorinated ether chain is free of biological accumulation compared with a perfluoroalkyl hydrocarbon chain; and the compound contains an active functional group, i.e., propenyl which can participate in addition reaction or polymerization reaction, so that the field of application is broad.

Description

technical field [0001] The invention relates to a method for synthesizing a photoisomerized fluorine-containing ether chain azobenzene compound that can participate in a polymerization reaction, and belongs to the technical field of azo photochromic materials. Background technique [0002] Due to the cis-trans isomerization of the azobenzene group under the action of light or heating, the fluorine-containing azobenzene compound changes the molecular geometric size and dipole moment of the compound accordingly, thereby changing the physical and chemical properties of the fluorine-containing azo compound. , wettability light-controlled tunable surface, drug release, protein adsorption controllable surface and so on have broad potential application prospects. [0003] It has been reported that fluorine-containing azobenzene compounds contain monofluorine substitution, trifluoromethyl end group or fluoroalkane side chain azobenzene compounds, but fluorine-containing ether chain ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C245/08C09K9/02
Inventor 高宇黄建宝黄焰根何创龙
Owner DONGHUA UNIV
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