ELECTROCHEMISTRY AND NEAR-INFRARED SPECTRA OF ANION RADICALS CONTAINING SEVERAL IMIDE OR QUINONE GROUPS

A series of aromatic compounds possessing imide and quinone electron-acceptor groups were prepared using Diels-Alder reactions. These linear, aromatic compounds were studied using cyclic voltammetry and reduced electrochemically to produce solutions of the corresponding anion radicals. The anion radical near-infrared spectra were recorded and showed bands over the range 700–1700 nm (log e 3.8-4.6). Most of the spectra are interpreted to arise from r*-71-* transitions. The spectra and E° values are consistent with ground states in which the odd electron is delocalized over two electrophores. © 1990, American Chemical Society. All rights reserved.