NOVEL MOLECULES FOR THE DESIGN OF ORGANIC CONDUCTORS - SYNTHESIS OF ETRACYANO-2,5-BIS(3-PHENYLPROPYL)-P-QUINODIMETHANE AND ,N'-DICYANO-2,5-BIS(3-PHENYLPROPYL)-P-QUINODIIMINE AND X-RAY STRUCTURE OF THE TCNQ DERIVATIVE
N. Martin et al., NOVEL MOLECULES FOR THE DESIGN OF ORGANIC CONDUCTORS - SYNTHESIS OF ETRACYANO-2,5-BIS(3-PHENYLPROPYL)-P-QUINODIMETHANE AND ,N'-DICYANO-2,5-BIS(3-PHENYLPROPYL)-P-QUINODIIMINE AND X-RAY STRUCTURE OF THE TCNQ DERIVATIVE, Journal of the Chemical Society. Perkin transactions. I, (19), 1993, pp. 2363-2368
The novel etracyano-2,5-bis(3-phenylpropyl)-p-quinodimethane 2 and ,N'
-dicyano-2,5-bis(3-phenylpropyl)-p-quinodiimine 3 in which the accepto
r TCNQ and DCNQI moieties are covalently linked to weak donors, phenyl
rings, by three methylene units have been synthesized and studied as
intended donor-acceptor-donor (D-A-D) systems. The cyclic voltammetry
data reveal two one-electron reversible reduction waves to the corresp
onding anion-radical and dianion. The novel molecules 2 and 3 behave,
in solution, as simple TCNQ and DCNQI derivatives, respectively. A str
uctural study by X-ray diffraction on the TCNQ-type molecule 2 shows a
very planar, nondistorted TCNQ ring with isolated D...A...D triplets
between the central TCNQ moiety of a molecule and two phenyl rings of
two other different molecules.