Thiophene-carbazole-thiophene derivative, preparation method and applications thereof

A thiophene derivative, thiophene technology, applied in chemical instruments and methods, instruments, color-changing fluorescent materials, etc., can solve the problems of limited large-scale application, monotonous color types, low coloring efficiency, etc., and achieve good electrochemical cycle stability, The effect of fast response time, reasonable optical contrast

Inactive Publication Date: 2017-09-15
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Inorganic electrochromic materials have good photochemical stability and fast response speed, but their high processing costs, monotonous color types, and low coloring efficiency limit their large-scale application in production and life.

Method used

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  • Thiophene-carbazole-thiophene derivative, preparation method and applications thereof
  • Thiophene-carbazole-thiophene derivative, preparation method and applications thereof
  • Thiophene-carbazole-thiophene derivative, preparation method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Example 1 Synthesis of 4,4'-bis(3,6-dithiophene-9hydro-carbazole-9)-1,1'-biphenyl

[0041] (1) Under nitrogen protection, 3,6-dibromocarbazole (1.43g, 3mmol), 2-thiophene boronic acid (0.896g, 7mmol), tetrakis (triphenylphosphine) palladium (0.2mmol) and sodium carbonate (2.0M, 5mL) was dissolved in a mixed solvent of tetrahydrofuran (20mL) and toluene (30mL), and the system was refluxed for 48 hours. After the system was cooled, it was extracted with deionized water and dichloromethane, and the obtained organic phase was added with anhydrous MgSO 4 After drying, it was concentrated under reduced pressure, and then separated and purified by column chromatography. The stationary phase was 300-400 mesh silica gel, and the mobile phase was dichloromethane / petroleum ether (volume ratio 1:3), and finally the intermediate product 3 was obtained as a white solid. , 0.68g of 6-dithiophenecarbazole compound, the yield is 68%. 1 H NMR (500MHz, CDCl 3 )δ:8.35(s,2H),8.12(s,H),7....

Embodiment 2

[0043] Example 2 Synthesis of 4,4'-bis(3,6-dithiophene-9hydro-carbazole-9)-1,1'-benzene

[0044] The synthesis method is the same as in Example 1, except that in step (2), 1,4-dibromobiphenyl is replaced by 1,4-dibromobenzene (235.90g / mol, 2mmol, 0.4718g), and finally obtained The target product is 0.62g, and the yield is 42%.

[0045] 4,4'-bis(3,6-dithiophene-9hydro-carbazole-9)-1,1'-benzene C 46 h 28 N 2 S 4 The MS (EI) characterization found to be 736.11.

Embodiment 3

[0046] Example 3 Synthesis of 4,4'-bis(3,6-dithiophene-9hydro-carbazole-9)-1,1'-terphenyl

[0047] The synthesis method is the same as in Example 1, except that in step (2), 1,4-dibromobiphenyl is replaced by 1,4-dibromoterphenyl (388.10g / mol, 2mmol, 0.7762g), and finally 0.55 g of the target product was obtained with a yield of 31%.

[0048] The MS (EI) characterization of 4,4'-bis(3,6-dithiophene-9hydro-carbazole-9)-1,1'-terphenyl C58H36N2S4 was found to be 888.01.

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Abstract

The present invention provides a thiophene-carbazole-thiophene derivative represented by a formula (I-a) or a formula (I-b), and a preparation method thereof, and applications of the thiophene-carbazole-thiophene derivative as a polymerization monomer in preparation of electrochromic films. According to the present invention, with the method of the present invention to synthesize the thiophene-carbazole-thiophene derivative, the yield of the final product is increased by 20%, and the film prepared through the biological polymerization of the thiophene-carbazole-thiophene derivative can be used in the electrochromic field, has excellent performances of short response time, reasonable optical contrast, good electrochemical stability and the like, and is the potential electrochromic material. The formulas (I-a) and (I-b) are defined in the specification.

Description

(1) Technical field [0001] The present invention relates to a thiophene-carbazole-thiophene derivative and a preparation method thereof, and the electropolymerization of the thiophene-carbazole-thiophene derivative into a film as a microporous structure material in the fields of electrochromism and the like . (2) Background technology [0002] With the rapid consumption of global energy and the continuous deterioration of the environment. Energy-saving and environmentally friendly materials have attracted widespread attention. Electrochromic materials are just such new functional materials that can change human production and lifestyle and contribute to the rational use of energy. The material has the advantages of abundant sources, simple device preparation process and low working voltage, and can be widely used in fields such as smart windows, electronic paper and displays. Conductive polymer-based electrochromic materials have become the most potential class of electro...

Claims

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Application Information

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IPC IPC(8): C07D409/14C07D519/00C09K9/02C08G61/12G02F1/15
CPCC07D409/14C07D519/00C08G61/124C08G61/126C08G2261/1424C08G2261/3223C08G2261/3241C08G2261/44C08G2261/54C09K9/02C09K2211/145C09K2211/1458C09K2211/1466G02F1/15
Inventor 张诚戴玉玉李维军闫拴马曲星星陈澜
Owner ZHEJIANG UNIV OF TECH
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