N. Martin et al., A NOVEL MOLECULE FOR THE DESIGN OF ORGANIC CONDUCTORS - -PHENYLPROPYL)-7,7,8,8-TETRACYANO-P-QUINODIMETHANE, Synthetic metals, 56(1), 1993, pp. 1730-1734
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.