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

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

Volume: 8 Issue: 10

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

Affiliation:

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

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.

Cite this article as:

Zhao Caiyun, Shi Jianwu, Li Chunli and Wang Hua, Efficient Synthesis of Substituted Dithieno[2,3-b:3',2'-d]siloles and A 10-Membered Silicon-Bridged Thiophene-Based Cyclophane, Letters in Organic Chemistry 2011; 8 (10) . https://dx.doi.org/10.2174/157017811799304179