Journal of the American Chemical Society p. 1422 - 1427 (1995)
Update date:2022-08-29
Topics:
Arias
Echegoyen
Wilson
Lu
Lu
Cathodic electrochemistry was performed for two methanofullerene derivatives, 3 and 4. Since it was possible to isolate the [6,6] closed isomeric forms of these derivatives (called simply methanofullerenes), the electrochemistry of the pure isomers was recorded. The electrochemical behavior of the corresponding mixtures, which also contained the [5,6] open forms (simply referred to as methanofulleroids), was also obtained. In the solvent mixture used, acetonitrile:toluene (1:5), no difference was observed for the potentials of the first four electrochemical waves of the two isomers. However, the methanofulleroid exhibited an anodically-shifted fifth reduction wave, relative to that corresponding to the methanofullerene. This difference in potential was 0.20 V for the fullerene-fulleroid isomers of both 3 and for those of 4. On the basis of the voltammetric data, the fulleroids behave more as triply degenerate systems, very much like the behavior for C60. This was anticipated, since they are, as is the parent C60, 60 π electron systems. However, the methanofullerenes have 58 π electrons, and part of their conjugated network is destroyed. The fullerenes exhibit what appear to be doubly degenerated LUMOs with a LUMO+ that is some 4-5 kcal/mol higher in energy. The presence of the methanofullerene was confirmed by simultaneous UV-vis spectrophotometry in the case of 3. Thermalization of isomeric mixtures of 3 and 4 resulted in the quantitative formation of the methanofullerene and the total disappearance of the methanofulleroid, consistent with previous results.
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