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Δ4,4‘-Dicyclopenta[2,1-b:3,4-b‘]dithiophene has been prepared from cyclopenta[2,1-b:3,4-b‘]bithiophen-4-one and its electrochemical and spectroscopic properties have been characterized. Its low HOMO−LUMO gap and facile electrochemical polymerization make it an attractive building block for low band gap conducting polymers. Films of poly-(Δ4,4‘-dicyclopenta[2,1-b:3,4-b‘]dithiophene) on electrodes have been characterized by cyclic voltammetry, electronic absorption spectroscopy, IR spectroscopy, and in situ conductivity measurements. The spectroscopic and electrochemical results confirm the formation of a polymeric material with long conjugation length and low band gap (ca. 0.5 eV). The intrinsic conductivity is consistent with this band gap.