A NOVEL MOLECULE FOR THE DESIGN OF ORGANIC CONDUCTORS - -PHENYLPROPYL)-7,7,8,8-TETRACYANO-P-QUINODIMETHANE

Two novel donor-acceptor-donor (D-A-D) systems (2 and 3) constituted b y TCNQ and DCNQI acceptor moieties and phenyl rings as weak donors moi eties respectively have been synthesized in a multistep process. The c rystallographical study by X-ray diffraction of compound 2 reveals a p lanar TCNQ central ring with the two donor phenyl rings in an orthogon al position and a trans conformation. The crystal packing geometry is forming defined isolated triplets between the acceptor of a molecule a nd the donors of two neighbouring molecules. Although a clear stacking pattern is apparent in the acceptor moieties, no significant interact ion is found between them. The cyclic voltammetry data of compounds 2 and 3 show two reversible one-electron single waves to the correspondi ng anion-radical and dianion with values similar to the parent TCNQ. T hese electrochemical data suggest that, in solution, these compounds b ehave essentially as 2,5-substituted TCNQ and DCNQI derivatives.