Molecular Crystals and Liquid Crystals, Vol.377, 289-292, 2002
A new narrow band gap electroactive silole containing polymer
Anew silole containing monomer,1,1-dihexyl-3,4-diphenyl-2,5-bis {2-(3,4-ethyl ethylenedioxy)thienyl}silole, was synthesized by Pd-catalyzed Stille coupling reaction of the necessary 2,5-dibromosilole and 2-stannylethylenedioxy-thiophene derivatives. This monomer can be easily electropolymerized (E-ox,E-m) = +0.29 V vs. Fc/Fc(+)) and yields an electroactive polymer with a low half-wave oxidation potential (E-1/2 = -0.38 V vs. Fc/Fc(+)). Spectroelectrochemistry has shown that the polymer switches between sky blue and yellow green upon doping. The low-lying LUMO levels of the siloles combined with the electron-rich character of the 3,4-ethylenedioxythiophene units confer upon this new polymer a narrow band gap of 1.4 eV (onset of the pi-pi* transition).