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 ∈ 3.8-4.6). Most of the spectra are interpreted to arise from π*-π* transitions. The spectra and E o values are consistent with ground states in which the odd electron is delocalized over two electrophores