A Highly Electron-Deficient Analogue of Aniline, Soluble Oligomers, and Their Redox Properties

The synthesis and
electrochemical oxidative coupling of a highly
electron-deficient analogue of aniline results in the formation of
soluble electron-deficient oligomers. Oligomers undergo related oxidation
and reduction processes that are separated by a wide potential range.
The mechanism behind this behavior is examined by cyclic voltammetry,
optical absorption spectroscopy, 1H NMR spectroscopy, and
density functional theory calculations. Mesomeric isomerization of
the oxidized oligomers leads to a very stable oxidized state that
requires a large (2.8 V) overpotential to return to the neutral form.