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Diseleno [2,3-b:3',2'-d] thiophene and preparation method thereof

The technology of selenophene and thiophene is applied in the field of diseleno[2,3-b:3',2'-d]thiophene and its preparation, which can solve the problems of low polarization and small thiophene derivatives, etc. Achieve the effects of high yield, simple and feasible preparation method, and simple and feasible preparation method

Active Publication Date: 2017-12-29
HENAN UNIVERSITY
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  • Abstract
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Problems solved by technology

However, since thiophene derivatives are limited by their own structures such as relatively small S atomic radius and low polarizability, further improvement of their performance is facing severe challenges.

Method used

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  • Diseleno [2,3-b:3',2'-d] thiophene and preparation method thereof
  • Diseleno [2,3-b:3',2'-d] thiophene and preparation method thereof
  • Diseleno [2,3-b:3',2'-d] thiophene and preparation method thereof

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Embodiment

[0045] In this example, diseleno[2,3-b:3',2'-d]thiophene has a structure as shown in formula (1),

[0046]

[0047] The synthesis route of diseleno[2,3-b:3',2'-d]thiophene in this embodiment is as follows,

[0048]

[0049] The preparation method of the diseleno[2,3-b:3',2'-d]thiophene of this embodiment comprises the following steps:

[0050] 1) Preparation of 5,5'-bis(trimethylsilyl)-3,3'-diselenophene (3):

[0051] Vacuum dry the 250mL Schlenk bottle for 0.5h, add 0.65g (2.29mmol) of 4-bromo-2-trimethylsilyl-selenophene (4) under the protection of argon, add 50mL of anhydrous Diethyl ether, stirred to dissolve compound (4) completely, cooled to -78°C, stirred for 30min; added dropwise n-BuLi (1.0mL, 2.5M in hexane, 11.73mmol, 1.0equiv) under the protection of argon, and kept at -78°C Reaction 2h. Then add 3.19 g of dry CuCl under the protection of argon 2 (23.45mmol2.0equiv), warming up to -55°C for 2h, slowly warming up to room temperature and stirring overnight....

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Abstract

The invention relates to diseleno [2,3-b:3',2'-d]thiophene and a preparation method thereof, belonging to the technical field of heterocyclic compounds. The diseleno[2,3-b:3',2'-d]thiophene disclosed by the invention has a structure shown as a formula (1). The diseleno [2,3-b:3',2'-d]thiophene disclosed by the invention is a building module of a novel organic functional material and seleno hetero thiophene helicene, and lays a foundation for development of an organic semiconductor material having excellent semiconductor properties and building of seleno hetero thiophene helicene.

Description

technical field [0001] The invention relates to diseleno[2,3-b:3',2'-d]thiophene and a preparation method thereof, belonging to the technical field of heterocyclic compounds. Background technique [0002] Thiophene derivatives have attracted extensive attention in the field of organic field effect transistors because of their excellent photoelectric properties. The research on the internal relationship and rules between the structure and properties of thiophene derivatives has made significant progress. However, because thiophene derivatives are limited by their own structures such as the relatively small radius of S atoms and low polarization, further improvement of their performance is facing severe challenges. Selenium atoms are easy to polarize and donate electrons, which makes selenophene derivatives have strong Se···Se interaction, which is reflected in organic semiconductor materials and often makes materials show superior performance. Replacing part of the sulfur at...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D517/14
CPCC07D517/14
Inventor 李春丽王华吴龙龙徐婉方茂鸿单震
Owner HENAN UNIVERSITY
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