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Silicon-phenyl-bithiophene derivatives and preparation method and application thereof

A technology of bithiophene and derivatives, applied in the fields of silicon organic 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: 2018-12-14
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-bithiophene derivatives and preparation method and application thereof
  • Silicon-phenyl-bithiophene derivatives and preparation method and application thereof
  • Silicon-phenyl-bithiophene derivatives and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Specific Synthesis of 5-(Tributyltin)-2,2'-Bithiophene Compounds

[0030] Add 2-2'-bithiophene (15mmol, 166g / mol, 2.5g) into a 250mL conical round-bottomed flask, under nitrogen protection, add 100mL of anhydrous and oxygen-free tetrahydrofuran solution, stir 2,2'-bithiophene fully Dissolve, slowly add n-butyllithium cyclohexane solution (15mmol, 2.5mol / L, 6mL) dropwise under nitrogen protection at -78°C, keep stirring at low temperature for two hours, then slowly add tributyltin chloride (20mmol, 1.2g / L, 5.5mL), stirred at -78°C for one hour, then returned to room temperature and stirred for 24 hours. After the reaction was completed, the reactant was concentrated, then chromatographed on a column with aluminum oxide, concentrated, and spin-dried to obtain The anhydrous liquid product was directly used in the next reaction without further purification.

Embodiment 2

[0032] Preparation of bis-(4-bromophenyl)-diphenylsilane

[0033] 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

[0035] Preparation of Silicon-Phenyl-Dithiophene Derivatives

[0036] Two-(4-bromophenyl)-diphenylsilane (1.48g, 3mmol) obtained in Example 2, and 5-(tributyltin)-2,2'-bithiophene (5.6g, 12mmol) obtained in Example 1 , Pd(PPh 3 ) 4(24.3mg, 0.021mmol) were added sequentially under 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 Chloromethane and water were extracted, and the obtained 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 (1:5), and finally a yellow Solid silicon-phenyl-dithiophene derivative 0.88g, yield 60%.MALDI-TOF-MS(M)(m / z):665.3[M+H] + .1H NMR (400MHz, CDCl 3 )δ7.65–7.60(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,4H) ...

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Abstract

The invention provides silicon-phenyl-bithiophene derivatives, a preparation method thereof and application of the silicon-phenyl-bithiophene derivatives as a monomer in preparation of an electrochromic material thin film through electrochemical polymerization. The silicon-phenyl-bithiophene derivatives are shown in a formula 1. A kind of silicon-phenyl-bithiophene derivatives are synthesized witha high yield of 60%, the thin film prepared through electrochemical polymerization by using the silicon-phenyl-bithiophene derivatives as the monomer exhibits a certain response speed and reasonableoptical contrast, and a potential application value is achieved in the field of electrochromism.

Description

(1) Technical field [0001] The invention relates to a silicon-phenyl-bithiophene 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): C07F7/08C09K9/02C25B3/10C25B3/29
CPCC09K9/02C09K2211/1014C09K2211/1007C09K2211/1092C25B3/29
Inventor 张诚罗菲菲李维军欧阳密
Owner ZHEJIANG UNIV OF TECH
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