Vinylene-linked pyridine-pyrrole donor–acceptor conjugated polymers

Vinylene-linked donor-acceptor-donor semiconducting polymers have been prepared by electropolymerization of the new monomers 2,6-bis[(E)-2-(1- methylpyrrol-2-yl)vinyl]pyridine and 2,5-bis[(E)-2-(1-methylpyrrol-2-yl)vinyl] pyridine. The monomers, consisting of two pyrrole donor units and a central pyridine acceptor ring spaced by vinylene links, differ by the substitution pattern around the central pyridine core (2,6 vs. 2,5-substitution). The electropolymerization process is more efficient on the 2,5-derivative. The new polymers show reversible electrochemistry dominated by a strong charge trapping effect. Poly(2,5-bis[(E)-2-(1-methylpyrrol-2-yl)vinyl]pyridine) energy levels closely match those of design rules for optimized polymers in combination with fullerene derivatives in bulk heterojunction solar cells. © 2011 Elsevier B.V.