Preparation method for di-thiophene-[2, 3-b; 3', 2'-d] thiophene

A technology of dithiophene and thiophene, which is applied in the field of preparation of trithiophene compounds, can solve problems such as the lack of a very effective and feasible method, achieve good social value and economic value, deprotection is efficient and feasible, and reduces side reactions. Effect

Inactive Publication Date: 2009-01-14
HENAN UNIVERSITY
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Problems solved by technology

[0027] In summary, so far, the various preparation methods of dithieno[2,3-b; 3',2'-d]thiophene (compound 1

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  • Preparation method for di-thiophene-[2, 3-b; 3', 2'-d] thiophene

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[0058] The preparation method of the present invention is specifically as follows:

[0059] (1) Preparation of [3,3']-bithiophene

[0060] The reactant 3-bromothiophene (20.0g, 0.123mol) was dissolved in anhydrous ether, the temperature was lowered to -78°C, n-BuLi (0.124mol) was added dropwise, and kept at -78°C for 1h. Add anhydrous CuCl 2 (0.124mol), slowly warming up to room temperature, stirring overnight. Add water to quench the reaction, add ether to extract, wash with 5% dilute hydrochloric acid, distilled water, saturated sodium bicarbonate, and distilled water, dry over anhydrous magnesium sulfate, and spin dry to obtain a crude product. The crude product was separated by silica gel column chromatography (eluent: petroleum ether) to obtain white crystal compound 8 (8.90 g, 87.3%).

[0061] Analysis of [3,3']-bithiophene: Mp (capillary) 132-133°C (lit.131-132°C). 1 H NMR (400MHz, CDCl 3 )δ7.38(2H, s), 7.36(2H, d, J=5.0Hz), 7.34(2H, d, J=5.0Hz). 13 C NMR (100MHz,...

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Abstract

The invention relates to a preparation method of dithiophene-[2, 3-b; 3`, 2`-d] thiophene, comprising the following steps of: (1) preparing [3, 3`]-bithiophene through the bromine-lithium exchange to 3-bromo-thiophene and the oxidative coupling to copper chloride; (2) preparing 2, 2`-dibromo-[3, 3`] bithiophene with high yield through the bromation to the prepared [3, 3`]-bithiophene with N-bromosuccinimide NBS; (3) producing 2, 2`-dibromo-5, 5`-bis(trimethylsilyl)-[3, 3`]-bithiophene by protecting the 2, 2`-dibromo-[3, 3`] bithiophene with a TMS group; (4) preparing 2, 5-bis(trimethylsilyl)-dithiophene-[2, 3-b; 3`, 2`-d] thiophene by implementing the bromine-lithium exchange and sulfo-ring closure to the 2, 2`-dibromo-5, 5`-bis(trimethylsilyl)-[3, 3`]-bithiophene; and (5) producing dithiophene-[2, 3-b; 3`, 2`-d] thiophene through the de-protection to the 2, 5- bis(trimethylsilyl)-dithiophene-[2, 3-b; 3`, 2`-d] thiophene with trifluoroacetic acid. The method adopts a group TMS assistant in dissolving to protect Alpha active sites of thiophene rings, thereby effectively reducing the generation of side reaction, and increasing the preparation yield of dithiophene-[2, 3-b: 3`, 2`-d] thiophene compounds by 40 to 47 percent.

Description

technical field [0001] The present invention relates to a preparation method of a trithiophene compound, in particular to a preparation method of dithieno[2,3-b; 3',2'-d]thiophene. Background technique [0002] There are six isomers of trithiophene compounds, as follows: [0003] [0004] Six isomers of trithiophene [0005] These trithiophene compounds have unique properties in organic conductors, organic semiconductors, organic electroluminescent materials, organic nonlinear optical materials, and organic thin film field-effect transistors due to their high charge mobility and good conjugation. It shows a very active application prospect, and has been favored by organic chemists and material scientists in recent years. At the same time, trithiophene derivatives also have certain applications in the fields of medicine, pesticides, and dyes. [0006] At present, the preparation of dithieno[2,3-b; 3',2'-d]thiophene (compound 1), which is an isomer of trithiophene compou...

Claims

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Application Information

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IPC IPC(8): C07D495/14
Inventor 王华王阳光王振王志华赵东锋赵春梅
Owner HENAN UNIVERSITY
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