Synthesis of novel heteroquaterphenoquinones and their electrochemical, structural, and spectroscopic characterization

The synthesis of heteroquaterphenoquinones involves a stepwise cross-coupling reaction or a more convenient method via the one-pot oxidative homocoupling reaction of heterocycle-substituted phenols. The quinones are stable in solid state and in solution. A reversible one-stage, two-electron oxidation reduction occurs up to dianions while a two-stage, one-electron oxidation reaction proceeds up to dications. The reduction and oxidation potentials depend on the aromaticity and ionization potentials of the incorporated heterocycles. Spectral analysis of the quinones is presented.