Sulfur atoms as bridges in polycyclic donor-σ-acceptor molecules

Abstract The syntheses of novel donor-σ-acceptor molecules (D-σ-A) containing TCNQ and DCNQI derivatives acceptor moieties have been carried out. Different heteroatoms (S, O) were used as electronically-non-interacting bridges between donor and acceptor and two links were used to obtain rigid planar molecules. The electronic spectra showed a characteristic charge transfer band near to 600 nm. The electrochemical behaviour of these compounds varies according to the acceptor moiety (TCNQ or DCNQI types). The presence of an oxidation wave in the voltammogramm reveals the uncommon ability to form both anion-radicals and cation-radicals in the same organic molecule.