Delta(4,4 ')-Dicyclopenta[2,1-b:3,4-b'ldithiophene has been prepared from cyclopenta[2,1-b:3,4blbithiophen-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-(Delta(4,4')- 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.