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Synthesis method and application of imidazole-thiophene aromatic heterocyclic ultra-short wavelength photochromic diarylethene compound

A diarylethene and photochromic technology, applied in chemical instruments and methods, optical recording/reproduction, color-changing fluorescent materials, etc., can solve the problems of low aromatic stability and achieve good sensitivity, good chemistry and Thermal stability, great application prospects

Inactive Publication Date: 2017-03-22
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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  • Synthesis method and application of imidazole-thiophene aromatic heterocyclic ultra-short wavelength photochromic diarylethene compound
  • Synthesis method and application of imidazole-thiophene aromatic heterocyclic ultra-short wavelength photochromic diarylethene compound
  • Synthesis method and application of imidazole-thiophene aromatic heterocyclic ultra-short wavelength photochromic diarylethene compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Example 1: [Compound 1o]:

[0035] In the general formula of molecular structure, when Ar is a thiophene ring, it constitutes a photochromic compound 1o, and its 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: The synthetic route of compound 1o:

[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 acetic acid containing liquid bromine was added dropwise under stirring, and the ice-bath reaction was continued for 8 h. Moisture liquid, Na for water phase 2 CO 3 After neutralization, extract with ether, combine the organic phases, and wash with saturated N...

Embodiment 2

[0056] Example 2: [Compound 2o]:

[0057] In the general formula of molecular structure, when R is methoxy, it constitutes photochromic compound 2o, and its name is: [1-(2,4-dimethylimidazol-5-yl), 2-(2- Methyl-5-p-methoxyphenylthiophen-3-yl)] perfluorocyclopentene, 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: the synthetic route of compound 2o:

[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 successiv...

Embodiment 3

[0077] Example 3: [Compound 3o]:

[0078] In the general formula, when R is hydrogen, the compound 3o is formed, and its name is: [1-(2,4-dimethylimidazol-5-yl), 2-(2-methyl-5-phenylthiophene -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: The synthetic route of compound 3o:

[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, after stirring for 20 min, 3 (4.0 g, 17 mmol) was added and the concentration was 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 phases...

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Abstract

The invention discloses a synthesis method and application of an ultra-short-wavelength photochromic diarylethene compound of an imidazole-thiophene aromatic heterocycle. The photochromic material can maintain good photochromic performance in a solution or a film, and is developed. The ring state has weak fluorescence in the range of 265-276 nm, while the closed-ring state has strong fluorescence in the range of 400-550 nm, which can be used for fluorescent light-controlled switches and anti-counterfeiting technology, and short-wavelength high-density holographic optical storage Materials, compared with symmetrical thiophene or benzothiophene perfluorocyclopentene materials, the cost of preparing materials is relatively low, and the application prospect is great.

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 Patents(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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