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

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.