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

A technology of triple thiophene and benzene derivatives, applied in chemical instruments and methods, color-changing fluorescent materials, organic chemistry, etc., can solve problems such as poor solubility and high rigidity of the main chain, and achieve improved stability, fast response speed, and increased total The effect of the degree of yoke

Inactive Publication Date: 2018-11-20
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Specific Synthesis of 2-(1,3,5-tris(2-thiophene)benzene)[4,4,5,5-tetramethyl-1,3,2-dioxaborane] Compound

[0025] 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, and 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 The organic phase was dried by adding anhydrous MgSO4, and then separated and purified by column chromatography. The stationary phase was 300 mesh silica gel, and the mobile phase was dichloromethane / petroleum ether (1:3). 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...

Embodiment 2

[0027] Preparation of Benzene-Terthiophene-Benzene Derivatives

[0028] 1-(2-(5-bromothiophene))-3,5-bis(2-thiophene)benzene (0.24g, 1.0mmol), 2-(1,3,5-tri(2-thiophene)benzene)[ 4,4,5,5-tetramethyl-1,3,2-dioxaborane] (0.90g, 2.0mmol), K 2 CO 3 (1.1g, 8mmol), 4ml water, 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 a yellow solid benzene-terthiophene-benzene derivative 1.15 g, the yield is 75%.MALDI-TOF-MS(M)(m / z):647.5[M+H] + . 1 H NMR (400MHz, CDCl 3 )δ7.77(s,6H),7.47–7.45(dd,4H),7.39(t,J...

Embodiment 3

[0030] Dissolve benzene-terthiophene-benzene derivatives 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 C...

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Abstract

The invention provides a benzene-terthienyl-benzene derivative as well as a preparation method and application of the benzene-terthienyl-benzene derivative as a monomer in preparing an electrochromicmaterial film through electrochemical polymerization. Benzene-terthienyl-benzene derivatives are synthesized at a higher yield (60 to 75 percent); and a film prepared by using the benzene-terthienyl-benzene derivative as the monomer through electrochemical polymerization shows a certain response speed and reasonable optical contrast and has potential application value in the field of electrochromism. (The formula is shown in the description).

Description

(1) Technical field [0001] The invention relates to a benzene-terthiophene-benzene derivative and its preparation method and application. (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, displays, automotive non-glare mirrors, and national d...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D333/08C09K9/02C08G61/12C08L65/00C08J5/18
CPCC07D333/08C08G61/126C08G2261/124C08G2261/228C08G2261/3223C08G2261/344C08G2261/354C08G2261/54C08J5/18C08J2365/00C09K9/02C09K2211/1416C09K2211/1458
Inventor 张诚罗菲菲李维军欧阳密戴玉玉闫栓马
Owner ZHEJIANG UNIV OF TECH
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