Efficient Synthesis of Substituted Dithieno[2,3-b:3',2'-d]siloles and A 10-Membered Silicon-Bridged Thiophene-Based Cyclophane

Author(s): Caiyun Zhao, Jianwu Shi, Chunli Li, Hua Wang.

Journal Name: Letters in Organic Chemistry

Volume 8 , Issue 10 , 2011

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Abstract:

Two new substituted dithieno[2,3-b:3',2'-d]siloles, 7,7-diphenyl-2,5-bis(trimethylsilyl) dithieno[2,3-b:3',2'- d]silole (1) and 7,7-diphenyl-2,5-dichloro-dithieno[2,3-b:3',2'-d]silole (2) were synthesized in 79.4% and 31.6% yields, respectively via the cross-coupling of 1,4-dilithiobutadienes with dichlorodiphenylsilane. An unexpected tetrachlorosubstituted 10-membered silicon-bridged thiophene-based cyclophane (3) was obtained in a high yield as 46.9% when the cross-coupling of 1,4-dilithiobutadiene reacted with dichlorodimethylsilane. In addition, the crystal structures of title compounds are described.

Keywords: Cross-coupling, dithieno[2, 3-b:3', 2'-d]silole, heterocycles, silicon-bridged thiophene-based cyclophane, polymer, transistors, dithienosilole, organic materials, solar cells, dichlorodimethylsilane

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Article Details

VOLUME: 8
ISSUE: 10
Year: 2011
Page: [728 - 731]
Pages: 4
DOI: 10.2174/157017811799304179
Price: $58

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