Properties of a Tetracyanopentacenequinone and Its Tetracyanoquinodimethane Derivative

Article abstract of DOI:10.1021/jo00256a019

A soluble tetracyanopentacenequinone was prepared.This quinone was converted to a TCNQ derivative by base-catalyzed reaction with malononitrile at high temperature.Variable-temperature NMR spectroscopy revealed a slow conformation change for the TCNQ derivative.Electrochemical reductions of the quinone and its TCNQ derivative were studied and UV-vis-NIR spectra of the neutrals, anion radicals, and dianions were recorded.The ions from the tetracyanopentacenequinone show very long wavelength NIR bands ascribed to strong perturbation of the quinone(radical-anion) by the cyano groups.