Abstract
Electroreduction and electrooxidation of monosubstituted N-methyl[60]fullerenopyrrolidines were studied by cyclic voltammetry and potentiostatic microelectrolysis in the cavity of an ESR spectrometer. Stepwise reversible transfer of three electrons to the fullerenopyrrolidine molecule results in the formation of stable radical anions (according to ESR, g = 2.0000, ΔH = 0.8 G), dianions, and radical trianions (according to ESR, g = 2.0015, ΔH = 1.5 G). The reduction potentials vary over narrow limits depending on the nature of the substituents in the pyrrolidine fragment of the compounds. Electrooxidation is irreversible and occurs in either one or two steps. For compounds containing the aniline, indole, or phenol fragment, the first step is associated with oxidation of these fragments and only after that, is the fullerenopyrrolidine core oxidized. Oxidation of the pyrrolidine fragment is substantially more difficult than that of tertiary amines.
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Nuretdinov, I.A., Yanilkin, V.V., Morozov, V.I. et al. Electrochemical reduction and oxidation of fullerenopyrrolidines and the ESR spectra of paramagnetic intermediates. Russian Chemical Bulletin 51, 263–268 (2002). https://doi.org/10.1023/A:1015499425490
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DOI: https://doi.org/10.1023/A:1015499425490