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Isolation of two seven-membered ring C-58 fullerene derivatives: C58F17CF3 and C58F18

Isolation of two seven-membered ring C-58 fullerene derivatives: C58F17CF3 and C58F18
Isolation of two seven-membered ring C-58 fullerene derivatives: C58F17CF3 and C58F18
Fluorination of C-60 at 550 degrees C leads to milligram quantities of two stable fullerene derivatives with 58-carbon cage structures: C58F18 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 sp(2) to sp(3) because of fluorine addition. The loss of carbon from C-60 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.
unsymmetrical c60me5o3h, fragmentation, carbon, c60f18, c-36
0036-8075
278-281
Troshin, Pavel A.
2b947e1c-315c-4b0b-9842-6cd6acdfc85c
Avent, Anthony G.
6fe5d51d-5f31-454f-938a-ec91c840f2ce
Darwish, Adam D.
25f723f4-6a72-4e21-a361-76b275b617ef
Martsinovich, Natalia
f7e874c8-e247-48b4-876f-6011fd3e8e86
Abdul-Sada, Ala'a K.
766a024d-ab64-4a35-8eff-99d86b13b987
Street, Joan M.
08227a16-6d20-495e-910c-d9bb89ddae9c
Taylor, Roger
16cca243-6646-4c6f-a563-321c2b1bb0f6
Troshin, Pavel A.
2b947e1c-315c-4b0b-9842-6cd6acdfc85c
Avent, Anthony G.
6fe5d51d-5f31-454f-938a-ec91c840f2ce
Darwish, Adam D.
25f723f4-6a72-4e21-a361-76b275b617ef
Martsinovich, Natalia
f7e874c8-e247-48b4-876f-6011fd3e8e86
Abdul-Sada, Ala'a K.
766a024d-ab64-4a35-8eff-99d86b13b987
Street, Joan M.
08227a16-6d20-495e-910c-d9bb89ddae9c
Taylor, Roger
16cca243-6646-4c6f-a563-321c2b1bb0f6

Troshin, Pavel A., Avent, Anthony G., Darwish, Adam D., Martsinovich, Natalia, Abdul-Sada, Ala'a K., Street, Joan M. and Taylor, Roger (2005) Isolation of two seven-membered ring C-58 fullerene derivatives: C58F17CF3 and C58F18. Science, 309 (5732), 278-281. (doi:10.1126/science.1111904).

Record type: Article

Abstract

Fluorination of C-60 at 550 degrees C leads to milligram quantities of two stable fullerene derivatives with 58-carbon cage structures: C58F18 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 sp(2) to sp(3) because of fluorine addition. The loss of carbon from C-60 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.

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More information

Published date: 8 July 2005
Keywords: unsymmetrical c60me5o3h, fragmentation, carbon, c60f18, c-36

Identifiers

Local EPrints ID: 20919
URI: http://eprints.soton.ac.uk/id/eprint/20919
ISSN: 0036-8075
PURE UUID: eb049b40-8afc-4c40-b0a7-2657a859d165

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Date deposited: 01 Mar 2006
Last modified: 15 Jul 2019 19:25

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Contributors

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

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