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Silicon-phenyl-terthiophene derivative and preparation method and application thereof

A technology of triple thiophene and derivatives, used in organic silicon compounds, chemical instruments and methods, electrolytic organic production, etc., can solve the problems of poor solubility and large rigidity of the main chain, and achieve good electrochromic performance and good redox ability. Effect

Inactive Publication Date: 2018-12-18
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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  • Silicon-phenyl-terthiophene derivative and preparation method and application thereof
  • Silicon-phenyl-terthiophene derivative and preparation method and application thereof
  • Silicon-phenyl-terthiophene derivative and preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0028] Specific synthesis of 2-tri(n-butyl)tin terthiophene compound 2,2':5',2"-terthiophene (15mmol, 3.7g) was added to a 250mL conical round-bottomed flask, under nitrogen protection, added without Water anaerobic tetrahydrofuran solution 100mL, stirring 2,2':5',2"-tertiary thiophene fully dissolved, slowly add n-butyllithium cyclohexane solution (15mmol, 2.5mol / L, 6mL), kept stirring at low temperature for two hours, then slowly added tributyltin chloride (20mmol, 1.2g / L, 5.5mL) dropwise, stirred at -78°C for one hour, then returned to room temperature and stirred for 24 hours, the reaction ended Finally, the reactant was concentrated, then chromatographed on a column of aluminum oxide, concentrated, and spin-dried to obtain an anhydrous liquid product, which was directly used in the next reaction without further purification.

Embodiment 2

[0030] Preparation of bis-(4-bromophenyl)-diphenylsilane

[0031] Add 1,4-dibromobenzene (20mmol, 4.7g) into a 250mL conical round-bottom flask, under nitrogen protection, add 100mL of anhydrous and oxygen-free ether solution, stir 1,4-dibromobenzene to fully dissolve, and Slowly add n-butyl lithium cyclohexane solution (21mmol, 8.4mL) dropwise under nitrogen protection at 78°C, keep stirring at low temperature for two hours, then slowly add dichlorodiphenylsilane (10mmol, 2.1mL) dropwise, and then return to Stir at room temperature for 12 hours. The solution was poured into water to quench the reaction, extracted three times with anhydrous ether, and the collected organic phase was dried over anhydrous magnesium sulfate overnight. After filtration, the solution was concentrated, and the crude product was recrystallized from absolute ethanol and dichloromethane to obtain 3.46 g of a white solid, with a yield of 70%. 1 H NMR (400MHz, CDCl 3 )δ7.46-7.44(8H,m,Ar-H),7.40-7.37(2...

Embodiment 3

[0033] Preparation of Silicon-Phenyl-Terthiophene Derivatives

[0034] Bis-(4-bromophenyl)-diphenylsilane (1.48g, 3mmol), and 2-tri(n-butyl)tin terthiophene (6.4g, 12mmol) obtained in Example 1, Pd(PPh 3 ) 4 (24.3mg, 0.021mmol) were added sequentially under a nitrogen atmosphere, 25ml of DMF (N,N-dimethylformamide) was added, the temperature was rapidly raised to 130°C, the system was refluxed for 16h, the reaction was stopped, cooled to room temperature, and respectively used Extract with dichloromethane and water, add anhydrous MgSO to the obtained organic phase After drying, then 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 The solid silicon-phenyl-terthiophene derivative 0.7g, the yield is 50%. MALDI-TOF-MS (M) (m / z): 828.9 [M+H] + . 1 H NMR (400MHz, CDCl 3)δ7.65–7.62(m,12H),7.50–7.46(m,2H),7.44–7.40(m,4H),7.30(d,J=3.8Hz,2H),7.25–7.22(m,2H) , 7.2...

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Abstract

The present invention provides a silicon-phenyl-terthiophene derivative as shown in Formula 1 and a preparation method thereof and application thereof as a monomer for electrochemically polymerizing an electrochromic material film; the method synthesizes the silicon-phenyl-terthiophene derivative in a higher yield (60%). The film obtained by electrochemically polymerizing the silicon-phenyl-terthiophene derivative as the monomer exhibits a fast response speed and reasonable optical contrast and has potential application value in the field of electrochromism.

Description

(1) Technical field [0001] The invention relates to a silicon-phenyl-terthiophene 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, displays,...

Claims

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Application Information

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IPC IPC(8): C07F7/08C25B3/10C09K9/02C25B3/29
CPCC09K9/02C07F7/0812C09K2211/1416C09K2211/1458C25B3/29
Inventor 张诚罗菲菲李维军欧阳密
Owner ZHEJIANG UNIV OF TECH
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