Journal of Organic Chemistry p. 5007 - 5010 (1988)
Update date:2022-09-26
Topics:
Kenny, P. W.
Jozefiak, T. H.
Miller, L. L.
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.
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