Chemistry: Isolation of two seven-membered ring C58 fullerene derivatives: C58F17CF3 and C58F 18

Pavel A. Troshin, Anthony G. Avent, Adam D. Darwish, Natalia Martsinovich, Ala'a K. Abdul-Sada, Joan M. Street, Roger Taylor

Research output: Contribution to journalArticlepeer-review

141 Citations (Scopus)

Abstract

Fluorination of C60 at 550°C leads to milligram quantities of two stable fullerene derivatives with 58-carbon cage structures: C 58F18 and C58F17CF3. The compounds were characterized by mass spectrometry and fluorine nuclear magnetic resonance spectroscopy, and the data support a heptagonal ring in the framework. The resulting strain, which has hindered past attempts to prepare these smaller quasi-fullerenes, is mitigated here by hybridization change of some of the carbons in the pentagons from sp2 to sp3 because of fluorine addition. The loss of carbon from C60 is believed to occur via sequential fluorine addition to a C-C single bond and an adjacent C=C bond, followed by loss of a :CF2 carbene.

Original languageEnglish
Pages (from-to)278-281
Number of pages4
JournalScience
Volume309
Issue number5732
DOIs
Publication statusPublished - 8 Jul 2005
Externally publishedYes

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