A Convenient Synthesis of Dithieno[3,2-b:2′,3′-d]thiophenes from Thiophene

Abstract

A new synthetic method for dithieno[3,2-b:2′,3′-d]thiophenes was developed. The approach involves three steps starting from thiophene: tetraiodation of thiophene, selective dialkynylations on the 2,5-positions of the tetraiodothiophene, and finally CuI/TMEDA catalyzed double annulations of 2,5-dialkynyl-3,4-diiodothiophenes by Na₂S, to afford dithieno[3,2-b:2′,3′-d]thiophene and its derivatives.

Key Words

thiophene - oligothiophenes - double annulations - tetraiodothiophene - semiconductors

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