The chemistry of anions derived from tetracyanodiphenoquinodimethane (TCNDQ)

Abstract

Dihydro-TCNDQ was prepared from biphenyl. The dianion salts of TCNDQ with alkali metal and tetraalkylammonium counter ions were prepared and characterized by their nmr and uv-visible spectra. Solutions of these dianions undergo two one-electron oxidations at −0.31 and −0.15 V in DMF. The electrochemistry is complicated by a second chemical process involving the monoanion [Formula: see text]. This was postulated to involve a dimerization of [Formula: see text] and this process was also implicated in the analysis of the uv-visible spectra of this anion. The [Formula: see text] anion has a solution esr spectrum of over 25 lines which have been analyzed by a computer simulation of the spectrum.