Sumanenetrione Anions Generated by Electrochemical and Chemical Reduction

The electrochemical reduction of sumanenetrione by cyclic voltammetry showed stepwise multielectron reduction. Cyclic voltammograms of the stepwise first and second one-electron reduction exhibited reversible waves with associated reduction potentials that were almost equivalent to those of C60. EPR...

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Bibliographic Details
Published in:Chemistry letters 2014-08, Vol.43 (8), p.1297-1299
Main Authors: Higashibayashi, Shuhei, Babu Shrestha, Binod, Morita, Yuki, Ehara, Masahiro, Ohkubo, Kei, Fukuzumi, Shunichi, Sakurai, Hidehiro
Format: Article
Language:English
Subjects:
Anions
Buckminsterfullerene
Energy gap
Fullerenes
Mathematical analysis
Radicals
Reduction
Symmetry
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Summary:The electrochemical reduction of sumanenetrione by cyclic voltammetry showed stepwise multielectron reduction. Cyclic voltammograms of the stepwise first and second one-electron reduction exhibited reversible waves with associated reduction potentials that were almost equivalent to those of C60. EPR studies of the chemically generated monoanion and dianion of sumanenetrione, in conjunction with theoretical calculations, revealed their structures. The radical anion exhibited C3v symmetric spin delocalization over the entire bowl structure. The radical anion exhibited several absorption bands covering the whole visible to near-IR region. The nature of excitations was assigned by SAC/SAC-CI SD-R calculations. The dianion has a singlet ground state with a large energy gap between the singlet and triplet states. The dianion, too, has C3v symmetry with delocalization over the bowl structure. The major contributing structure of the dianion is the closed-shell configuration rather than the open-shell biradical configuration.
ISSN:0366-7022
1348-0715
DOI:10.1246/cl.140351