Synthesis, electrochemical properties and crystal structure of thiophene fused halogen containing tcnq and dcnqi derivatives with /spl pi/-extended systems

A comparative study of x-extended acceptor molecules containing the tetracyano-p-quinodimethane (TCNQ) and dicyano-p-quinodiimine (DCNQI) moieties, bearing halogen atoms (fluorine or chlorine) on the aromatic backbone is described. Due to the steric hindrance, halogen DCNQI derivatives containing a fused thiophene ring exhibited the best acceptor abilities. An X-ray crystallographic analysis of the chlorosubstituted thiophene fused TCNQ derivative revealed a non planar molecule, packed as dimers, and the presence of Cl-N interactions in the crystal packing. F N/cN