Method for synthesizing ultrashort-wavelength photochromic diarylethene compound by using imidazole-thiophene aromatic heterocycle and application of compound

A diarylethene, photochromic technology, applied in chemical instruments and methods, optical recording/reproducing, color-changing fluorescent materials, etc., can solve problems such as low aromatic stability, achieve good sensitivity, and have great application prospects , the effect of good chemical and thermal stability

Inactive Publication Date: 2014-10-15
JIANGXI SCI & TECH NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The imidazole five-membered aromatic heterocyclic ring has low aromatic stability energy, so it can be used to design and synthesize diarylethene molecules containing imidazole rings. So far, the asymmetric ultrashort-wavelength all- Fluorocyclopentene diarylethene compounds have not yet been reported in any literature and patents

Method used

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  • Method for synthesizing ultrashort-wavelength photochromic diarylethene compound by using imidazole-thiophene aromatic heterocycle and application of compound
  • Method for synthesizing ultrashort-wavelength photochromic diarylethene compound by using imidazole-thiophene aromatic heterocycle and application of compound
  • Method for synthesizing ultrashort-wavelength photochromic diarylethene compound by using imidazole-thiophene aromatic heterocycle and application of compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Example 1: [compound 1o ]:

[0035] In the general formula of the molecular structure, when Ar is a thiophene ring, it constitutes a photochromic compound 1o, whose name is: [1-(2,4-dimethylimidazol-5-yl), 2-(2,5-dimethylthiophen-3-yl)] perfluorocyclopentene ( 1o ), the structural formula is as follows:

[0036] ,

[0037] The synthetic scheme of this novel perfluorocyclopentene diarylethene photochromic compound is shown in Scheme 1:

[0038] Scheme 1: Compounds 1o The synthetic route of:

[0039] ;

[0040] Concrete synthetic steps are as follows:

[0041] 1, 3-bromo-2,5-dimethylthiophene ( 3 )

[0042] Under ice bath conditions, 2,5-dimethylthiophene ( 2 ) (22.5 g, 200.0 mmol) was dissolved in acetic acid, and the acetic acid containing liquid bromine was added dropwise under stirring, and the ice bath reaction was continued for 8 h, and the aqueous solution was added, and the aqueous phase was used Na 2 CO 3 After neutralization, extract with ether, ...

Embodiment 2

[0056] Example 2: [compound 2o ]:

[0057] In the molecular structure formula, when R is a methoxy group, it constitutes a photochromic compound 2o , whose name is: [1-(2,4-dimethylimidazol-5-yl), 2-(2-methyl-5-p-methoxyphenylthiophen-3-yl)]perfluorocyclopentyl Alkenes, the structural formula is as follows:

[0058] ,

[0059] The synthetic scheme Scheme 1 of this novel diaryl perfluorocyclopentene photochromic compound is shown in Scheme 1: Scheme 2: Compound 2o The synthetic route of:

[0060] ;

[0061] Concrete synthetic steps are as follows:

[0062] 1. 3,5-dibromo-2-methylthiophene ( 2 )

[0063] Under the condition of ice bath, dissolve 2-methylthiazene (25.6 g, 261.4 mmol) in acetic acid, add dropwise acetic acid containing liquid bromine under stirring, continue to react in ice bath for 8 h, add water solution, and use Na 2 CO 3 After neutralization, extract with ether, combine the organic phases, and wash with saturated Na 2 CO 3 and aqueous solution...

Embodiment 3

[0077] Example 3: [compound 3o ]:

[0078] In the general formula, when R is hydrogen, it constitutes a compound 3o , and its name is: [1-(2,4-dimethylimidazol-5-yl), 2-(2-methyl-5-phenylthiophen-3-yl)]perfluorocyclopentene ( 3o ), the structural formula is as follows:

[0079] ;

[0080] The synthetic scheme Scheme 3 of this novel diaryl perfluorocyclopentene photochromic compound is shown in:

[0081] Scheme 3: Compounds 3o The synthetic route of:

[0082] ;

[0083] Concrete synthetic steps are as follows:

[0084] 1. 3-bromo-2-methyl-5-phenylthiophene ( 4 )

[0085] Under nitrogen protection, bromobenzene (3.0 g, 19 mmol) and Pd(PPh 3 ) 4 (0.5 g) was dissolved in 80 mL THF, stirred for 20 min and added 3 (4.0 g, 17mmol) and a concentration of 2.0 mol / L Na 2 CO 3 The solution was 50 mL, heated to reflux for 16 h, stopped the reaction, and cooled to room temperature. The liquids were separated, the aqueous phase was extracted with ether, the organic phas...

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Abstract

The invention discloses a method for synthesizing an ultrashort-wavelength photochromic diarylethene compound by using imidazole-thiophene aromatic heterocycle and an application of the compound. A photochromic material can maintain good photochromic performance in a solution or film, has weaker fluorescence when the open-loop state ranges from 265 nm to 276 nm, has high fluorescence when the closed-loop state ranges from 400 nm to 550 nm, can be applied to a fluorescent photoswitch, an anti-forgery technology, a short-wavelength high-density holographic optical storage material and the like, and compared with the symmetrical thiophene or benzothiophene octafluorocyclopentene material, the material preparing cost is lower, and the application prospect is broader.

Description

technical field [0001] The invention relates to a synthesis method and application of an imidazole-thiophene aromatic heterocyclic ultrashort-wavelength photochromic diarylethene compound. Background technique [0002] With the rapid development of information storage technology, people put forward higher and higher requirements for the capacity, data transmission rate and response time of optical information storage materials. The exploration of organic photochromic compounds as erasable and rewritable information materials is particularly attractive, because compared with inorganic materials, organic materials have high sensitivity, fast response, easy to form thin films, relatively low raw material prices, and can be passed through Chemical modification greatly adjusts the structure and properties of materials to meet storage requirements and other advantages, but there are also disadvantages such as poor photothermal stability and fatigue resistance. In recent years, th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D409/08C07D413/08C07D401/08C07D233/64C09K9/02C09K11/06G11B7/241H03K17/94
CPCC07D233/64C07D401/08C07D409/08C07D413/08C09K9/02C09K11/06C09K2211/1044C09K2211/1092
Inventor 蒲守智王仁杰董小荣刘刚范丛斌崔士强刘宏亮
Owner JIANGXI SCI & TECH NORMAL UNIV
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