The novel 7,7,8,8-tetracyano-2,5-bis(3-phenylpropyl) -p-quinodimethane 2 and N,N'-dicyano-2.5bis(3-phenylpropyl)-p-quinodiimine 3 in which the acceptor TCNQ and DCNQl 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 corresponding anion-radical and dianion. The novel molecules 2 and 3 behave, in solution, as simple TCNQ and DCNQI derivatives, respectively.A structural study by X-ray diffraction on the TCNQ-type molecule 2 shows a very planar, nondistorted TCNQ ring with isolated D 9 e A 0 . e D triplets between the central TCNQ moiety of a molecule and two phenyl rings of two other different molecules.
Paper 3101437A