A six-stage amphoteric redox hydrocarbon radical 3• containing three phenalenyl units was prepared. Cyclic voltammogram of 3• exhibits six reversible redox waves with a small numerical sum (E1sum) of first oxidation (E1ox) and reduction (E1red) potentials. Some redox states of 3• were successfully generated from the neutral 3• and characterized by NMR, ESR, UV-vis-NIR spectroscopies, and theoretical calculations. The spin and the charges are delocalized over the entire C3 molecule of 33+, 3•2+, 3•, and 33−. On the other hand, 3•2− shows the localization of the spin on one phenalenyl unit; these results are consistent with the distorted C2 structure caused by the Jahn-Teller effect.
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Kubo et al. (2001) studied this question.
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