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Novel photochromic azobenzene compound and synthesis method thereof

A synthetic method and photochromic technology, applied in the direction of organic chemistry, can solve the problems of anhydrous and oxygen-free solvent treatment, expensive catalysts, etc., achieve significant economic and environmental benefits, simple post-treatment of products, and high conversion rate Effect

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

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Problems solved by technology

[0008] In the patent EP 802173, there is also a coupling reaction between aromatic halides and aniline. There are also problems such as expensive catalysts and solvents that need to be anhydrous and oxygen-free. The reaction formula is shown in formula 5

Method used

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  • Novel photochromic azobenzene compound and synthesis method thereof
  • Novel photochromic azobenzene compound and synthesis method thereof
  • Novel photochromic azobenzene compound and synthesis method thereof

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Experimental program
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Effect test

Embodiment 1

[0045] A preparation method of a novel azobenzene compound N-[4-[2-(4-methoxyphenyl)diazenyl]phenyl]-2-nitroaniline (compound 4), comprising the following steps :

[0046] (1) In the 250mL three-necked flask, add 6.15g compound 1, 12.9mL mass fraction is 36% hydrochloric acid, 100mL deionized water, stir and make it dissolve completely, obtain homogeneous mixed solution, add to described mixed solution under stirring condition 38 mL of NaNO with a mass fraction of 10% was added dropwise to 2 Solution, stirred and reacted for 1 h at 0-5°C to obtain a diazotization reaction solution, namely an aqueous solution of compound 2;

[0047] (2) add 4.56g aniline in the 500mL three-necked flask, 4.3mL mass fraction is the hydrochloric acid of 36%, 100mL deionized water, stir and make it fully dissolve, form the coupling liquid of aniline and hydrochloric acid; Step (1) gained The diazotization reaction solution is slowly added dropwise to the coupling solution, the temperature of the ...

Embodiment 2

[0050] A preparation method of a novel azobenzene compound N-[4-[2-(4-methoxyphenyl)diazenyl]phenyl]-2-nitroaniline (compound 4), comprising the following steps :

[0051] Step (1) and step (2) of the present embodiment adopt the same steps as step (1) and step (2) in embodiment 1;

[0052] Step (3): Add 0.1g of compound 3, 0.104g of 2-nitrochlorobenzene, and 0.064g of KF / Al to a 50mL single-necked round bottom flask. 2 o 3 , N,N-Dimethylformamide 5mL, reflux at 130°C for 3h, after the reaction is complete, remove the catalyst by filtration, transfer the filtrate to a separatory funnel, add 20mL ethyl acetate and 20mL saturated saline to remove the solvent N,N-di Methylformamide, so repeatedly washed 2-3 times, separated the organic layer, and distilled off the solvent under reduced pressure to obtain the crude product. The crude product was obtained, and the crude product was separated by column chromatography. The mixed solution of ethyl acetate and sherwood oil is eluent...

Embodiment 3

[0054] A preparation method of a novel azobenzene compound N-[4-[2-(4-methoxyphenyl)diazenyl]phenyl]-2-nitroaniline (compound 4), comprising the following steps :

[0055] Step (1) and step (2) of the present embodiment adopt the same steps as step (1) and step (2) in embodiment 1;

[0056] Step (3): Add 0.1g of compound 3, 0.138g of 2-nitrochlorobenzene, and 0.064g of KF / Al to a 50mL single-necked round bottom flask. 2 o 3 , N,N-Dimethylformamide 5mL, reflux at 130°C for 3h, after the reaction is complete, remove the catalyst by filtration, transfer the filtrate to a separatory funnel, add 20mL ethyl acetate and 20mL saturated saline to remove the solvent N,N-di Methylformamide, so repeatedly washed 2-3 times, separated the organic layer, and distilled off the solvent under reduced pressure to obtain the crude product, which was separated by column chromatography, and 300 mL of ethyl acetate with a volume ratio of 1:15 The mixed solution with sherwood oil is eluent elution...

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Abstract

The invention provides a novel photochromic azobenzene compound and a synthesis method thereof and relates to a novel compound N-[4-[2-(4-methoxyphenyl) diazenyl] phenyl]-2-nitroaniline with a photochromic property and a synthesis method of the novel compound. The synthesis method comprises diazonium coupling reaction and coupling reaction between aromatic amine and aromatic halides. According to the invention, coupling reaction conditions of aromatic amine and aromatic halides are very simple, to be specific, only alkali metal fluorides with equal molar mass are added into reaction liquid, and reflux is carried out at 130 DEG for 3 h; a solvent is not required to be subjected to anhydrous anaerobic treatment, that reaction is carried out under nitrogen or argon atmosphere is not required, no side reaction is generated, aftertreatment of the product is simple, the conversion rate is higher, the yield of the target product is 48-74%, in addition, equipment adopted by the invention is relatively simple, the cost is low, and obvious economic benefits and environment-protection benefits are realized. The defects, in the prior art, that coupling reaction between aromatic amine and aromatic halides can be carried out at high temperature, with existence of inorganic base and under anhydrous anaerobic inert atmosphere usually, the reaction time is long, side reaction is multiple and the yield is low are overcome.

Description

technical field [0001] The invention relates to a novel azobenzene compound and a synthesis method thereof, in particular to a compound N-[4-[2-(4-methoxyphenyl)diazenyl]benzene with photochromic properties. Base]-2-nitroaniline and its synthetic method. Background technique [0002] Azobenzene derivatives containing chromophores (-N=N-) can not only be used as dye intermediates and analytical reagents, but also, due to the fact that these substances can be reversibly in both cis and trans conformations under irradiation of appropriate wavelengths (as shown in Formula 1) are mutually converted, and its structure and absorption spectrum produce reversible changes. This photochromic property makes it widely used in optical information storage materials, molecular devices, nonlinear optical materials, liquid crystal materials, It is widely used in bioactive light regulation, nanomaterials and other fields. [0003] [0004] At present, there are four most common synthetic ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C245/08
Inventor 王峥乐英
Owner HUBEI UNIV
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