Benzene-tetrathiophene-benzene derivative as well as preparation method and application thereof

A technology of benzene derivatives and bithiophene, which is applied in the field of benzene-quaterthiophene-benzene derivatives and its preparation and application, can solve the problems of high rigidity of the main chain and poor solubility, and achieve good electrochromic performance and good oxidation The effect of restoring power

Inactive Publication Date: 2018-12-21
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, unsubstituted polythiophene has poor solubility in organic solvents due to the high rigidity of the main chain, thus limiting its practical application.

Method used

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  • Benzene-tetrathiophene-benzene derivative as well as preparation method and application thereof
  • Benzene-tetrathiophene-benzene derivative as well as preparation method and application thereof
  • Benzene-tetrathiophene-benzene derivative as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Specific Synthesis of 2-(1,3,5-tris(2-thiophene)benzene)[4,4,5,5-tetramethyl-1,3,2-dioxaborane] Compound

[0026] 1-(2-(5-bromothiophene))-3,5-bis(2-thiophene)benzene (1.62g, 4.0mmol), bis(pinacolate)diboron (2.03g, 8.0mmol), KOAc (0.79g, 8.8mmol) and Pd(PPh 3 )Cl 2 (10.0mg, 0.007mmol) was dissolved in 60mL of dioxane under the protection of nitrogen, rapidly heated to 130°C, the system was refluxed for 24h, the reaction was stopped, cooled to room temperature, extracted with deionized water and dichloromethane, and the obtained The organic phase was dried by adding anhydrous MgSO4, then separated and purified by column chromatography, the stationary phase was 300 mesh silica gel, the mobile phase was dichloromethane / petroleum ether (1:3), and finally a green solid 2-(1,3 ,5-tris(2-thiophene)benzene)[4,4,5,5-tetramethyl-1,3,2-dioxaborane] 1.64g, the yield was 91%. 1 H NMR (500MHz, CDCl 3 )δ7.74(dd, J=6.0,1.5Hz,3H),7.36(d,J=3.7Hz,2H),7.27–7.25(d,J=3.8Hz,2H),7.21(d,J=...

Embodiment 2

[0028] Preparation of Benzene-Quadrthiophene-Benzene Derivatives

[0029] 1-(5-bromo-2,2':5',2"-terthiophene)-3,5-di(2-thiophene)benzene (0.57g, 1.0mmol), 2-(1,3,5- Tris(2-thiophene)benzene)[4,4,5,5-tetramethyl-1,3,2-dioxaborane] (0.90g, 2.0mmol), K 2 CO 3 (1.1g, 8mmol), water 4ml, Pd(PPh 3 ) 4 (10.0mg, 0.007mmol) was added sequentially under a nitrogen atmosphere, 6ml of toluene was added, the temperature was rapidly raised to 130°C, the system was refluxed for 24h, the reaction was stopped, cooled to room temperature, extracted with deionized water and dichloromethane, and the obtained organic phase was added to After drying with anhydrous MgSO4, separate and purify by column chromatography, the stationary phase is 300 mesh silica gel, the mobile phase is dichloromethane / petroleum ether (1:5), and finally orange solid benzene-quaterthiophene-benzene derivatives are obtained 0.97g, the yield is 60%.MALDI-TOF-MS(M)(m / z):812.4[M+H] + . 1 H NMR (400MHz, CDCl 3)δ7.77(d, J=...

Embodiment 3

[0031] Benzene-quaterthiophene-benzene was dissolved in dichloromethane / acetonitrile solution (volume ratio 7:3), tetrabutylammonium hexafluorophosphate (TPAPF 6 ) as the electrolyte, constant volume, ultrasonic 3min, until completely dissolved, the electrode is platinum wire as the counter electrode, Ag / AgCl electrode as the reference electrode, and ITO conductive glass as the three-electrode system of the working electrode, using cyclic voltammetry 0- 1.6V electrochemical polymerization film formation, the polymerization conditions are: the voltage range is 0-1.6v, the scanning speed is 0.1v / s, and the number of scanning circles is 20 circles. in TPAPF 6 / dichloromethane / acetonitrile (v:v,7:3) for 1min dedoping for performance testing, all electrochemical tests were performed at TPAPF 6 / dichloromethane / acetonitrile (v:v, 7:3) for testing. Cyclic voltammetry, spectroelectrochemical and electrochromic test step voltage is 0V-1.6V, attached figure 1 , 2 , 3, 4 are the CV c...

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Abstract

The invention provides a benzene-tetrathiophene-benzene derivative as shown in a formula 1 and a preparation method thereof, and application of the benzene-tetrathiophene-benzene derivative as a monomer in electrochemical polymerization of electrochromic material films. The benzene-tetrathiophene-benzene derivative is synthesized at higher yield (50%-60%). The film prepared based on the benzene-tetrathiophene-benzene derivative as a monomer through electrochemical polymerization has fast respond speed, reasonable optical contrast, high electrochemical stability, and has potential application value in the electrochromic field. (The formula is shown in the description).

Description

(1) Technical field [0001] The invention relates to a benzene-quaterthiophene-benzene structure derivative, a preparation method thereof and an application as an electrochromic material. (2) Background technology [0002] The energy crisis and environmental pollution have made our living environment accept unprecedented challenges. Therefore, how to effectively use renewable energy such as wind energy and solar energy is a current research hotspot. According to the function, solar materials are mainly divided into photochemical energy conversion materials, photothermal conversion materials, photoelectric conversion materials and photochromic materials controlled by light energy. Among them, the photochromic materials controlled by light energy include thermochromic materials, photochromic materials and electrochromic materials. Electrochromism is the most widely studied because of its broad application prospects. EC materials can be used in smart windows, biosensors, displ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D333/08C09K9/02C08J5/18C08G61/12
CPCC07D333/08C08G61/126C08J5/18C08J2365/00C09K9/02C09K2211/1458
Inventor 李维军罗菲菲张诚欧阳密戴玉玉闫栓马
Owner ZHEJIANG UNIV OF TECH
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