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

Melvin H Hall; Philip Shevlin; Huajun Lu; Anthony Gichuhi; Curtis Shannon

doi:10.1021/jo0521706

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

J Org Chem. 2006 Apr 28;71(9):3357-63. doi: 10.1021/jo0521706.

Authors

Melvin H Hall¹, Philip Shevlin, Huajun Lu, Anthony Gichuhi, Curtis Shannon

Affiliation

¹ Department of Chemistry and Physics, LaGrange College, LaGrange, Georgia 30240, USA. mhall@lagrange.edu

PMID: 16626114
DOI: 10.1021/jo0521706

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.