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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