Electrochemically induced isomerization of a fulleroid to a methanofullerene

Journal Article · Wed Sep 07 04:00:00 EDT 1994 · Journal of the American Chemical Society

DOI:https://doi.org/10.1021/ja00097a053· OSTI ID:102782

Eiermann, M; Wudl, F ^[1]; Prato, M ^[2]; Maggini, M ^[3]

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1. Univ. of California, Santa Barbara, CA (United States)
2. Universita di Trieste (Italy)
3. Centro Meccanismi di Reazioni Organiche del CNR, Padova (Italy)

Though six electrons can be reversibly added to C{sub 60}, the influence of the {pi}-electron count on cyclic voltammetry (CV) has not yet been investigated in detail. Saturation of a double bond of C{sub 60} in methanofullerenes causes a negative shift of about 50-150 mV for the first three waves. Here we report the synthesis and electrochemical investigation on a p-(methoxycarbonyl)-phenyl-substituted fulleroid (2) and its methanofullerene isomer (3). Further, by a combination of CV and UV - vis spectrophotometry, we show that (1) 2 and 3 have only very slightly different electron acceptor character and (2) 2 is converted to 3 upon addition of a third electron in 2. 13 refs., 2 figs.

• Sponsoring Organization: USDOE
• OSTI ID: 102782
• Journal Information: Journal of the American Chemical Society, Journal Name: Journal of the American Chemical Society Journal Issue: 18 Vol. 116; ISSN JACSAT; ISSN 0002-7863
• Country of Publication: United States
• Language: English

Related Subjects

40 CHEMISTRY
ACETONITRILE
DIAZO COMPOUNDS
ELECTROCHEMISTRY
FULLERENES
ISOMERIZATION
NUCLEAR MAGNETIC RESONANCE
SYNTHESIS
TOLUENE
ULTRAVIOLET SPECTRA
VOLTAMETRY