Electron-acceptor-induced isomerization of aryl [6,5] open fulleroids to [6,6] closed methanofullerenes and the electrochemical evaluation of their free energy difference

The Journal of Organic Chemistry
Melvin H HallCurtis Shannon

Abstract

The thermal and photochemical rearrangements of a series of aryl substituted [6,5] open fulleroids to [6,6] closed methanofullerenes are accelerated in the presence in of electron acceptors. These [6,5] open fulleroids, facilitated by electron acceptors, rearrange thermally by a zwitteronic-type intermediate, while the photochemical reactions proceed via an excited-state electron-transfer process. The oxidation potentials of these [6,5] open fulleroids and their corresponding [6,6] closed methanofullerenes isomers have been evaluated. The free energy difference between the [6,5] open fulleroids and their corresponding [6,6] closed isomers have been estimated from the difference in their oxidation potentials.

References

Feb 19, 2002·Chemical Reviews·Nazario MartínIgnacio Pérez

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Citations

Jun 19, 2013·Chemical Reviews·Michio YamadaShigeru Nagase
Jan 16, 2015·Chemical Reviews·Olga V BoltalinaSteven H Strauss
May 20, 2015·Journal of the American Chemical Society·Maira R CerónLuis Echegoyen

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