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Isolation and characterisation of both the first fluoroxyfluorofullerene C60F17OF and oxahomofluorofullerenol C60F17O.OH

Isolation and characterisation of both the first fluoroxyfluorofullerene C60F17OF and oxahomofluorofullerenol C60F17O.OH
Isolation and characterisation of both the first fluoroxyfluorofullerene C60F17OF and oxahomofluorofullerenol C60F17O.OH
The first fluoroxyfluorofullerene C60F17OF (A) has been isolated from the fluorination of [60]fullerene with a mixture of MnF3 and K2NiF6 at 480ºC. This compound has a shorter HPLC retention time than the isomeric fluorofullerene ethers (oxahomofullerenes) and is less stable towards El mass spectrometry. It fragments by losing OF as a single entity and shows no formation of C60O as a fragment ion. By contrast, the ethers fragment by first losing a number of F atoms and then CO, and ultimately show also the presence of C60O, whilst epoxides lose CO as a main fragmentation step and do not give C60O. The first oxahomofluorofullerenol C60F17O.OH (B) has been isolated from the UV-irradiation of a toluene solution of C60F18 in air during 65 It and readily eliminates HF due to adjacent F and OH groups during El mass spectrometry. The structures of both the compounds have been deduced from I D and 2D 19F NMR spectroscopy. Just as oxygen inserts into FC-CF bonds of C60F18 to give ethers, so insertion into a C-F bond gives A. The oxahomofluorofullerenol B is produced by SN2' substitution of F by OH, followed by oxygen insertion into a 6:5-bond (αβ to the OH group) giving a motif not seen previously in fluorofullerenes.
Fullerenes, Fluoroxyfluorofullerene, Oxahomofluorofullerenol, Ethers, Fluorine NMR
0022-1139
185-192
Darwish, A.D.
6f919f23-7ae3-49cf-8bf2-938a70987964
Abdul-Sada, A.K.
565c6808-e54c-4b87-ad95-1d84535389cc
Avent, A.G.
ef621cee-165f-4e31-8f28-ec83bba95618
Street, J.M.
186366c0-692b-4236-bb93-e2a3b6e9395c
Taylor, R.
1abcd415-ae2c-4e95-a761-6948ce7f4d32
Darwish, A.D.
6f919f23-7ae3-49cf-8bf2-938a70987964
Abdul-Sada, A.K.
565c6808-e54c-4b87-ad95-1d84535389cc
Avent, A.G.
ef621cee-165f-4e31-8f28-ec83bba95618
Street, J.M.
186366c0-692b-4236-bb93-e2a3b6e9395c
Taylor, R.
1abcd415-ae2c-4e95-a761-6948ce7f4d32

Darwish, A.D., Abdul-Sada, A.K., Avent, A.G., Street, J.M. and Taylor, R. (2003) Isolation and characterisation of both the first fluoroxyfluorofullerene C60F17OF and oxahomofluorofullerenol C60F17O.OH. Journal of Fluorine Chemistry, 121 (2), 185-192. (doi:10.1016/S0022-1139(03)00014-9).

Record type: Article

Abstract

The first fluoroxyfluorofullerene C60F17OF (A) has been isolated from the fluorination of [60]fullerene with a mixture of MnF3 and K2NiF6 at 480ºC. This compound has a shorter HPLC retention time than the isomeric fluorofullerene ethers (oxahomofullerenes) and is less stable towards El mass spectrometry. It fragments by losing OF as a single entity and shows no formation of C60O as a fragment ion. By contrast, the ethers fragment by first losing a number of F atoms and then CO, and ultimately show also the presence of C60O, whilst epoxides lose CO as a main fragmentation step and do not give C60O. The first oxahomofluorofullerenol C60F17O.OH (B) has been isolated from the UV-irradiation of a toluene solution of C60F18 in air during 65 It and readily eliminates HF due to adjacent F and OH groups during El mass spectrometry. The structures of both the compounds have been deduced from I D and 2D 19F NMR spectroscopy. Just as oxygen inserts into FC-CF bonds of C60F18 to give ethers, so insertion into a C-F bond gives A. The oxahomofluorofullerenol B is produced by SN2' substitution of F by OH, followed by oxygen insertion into a 6:5-bond (αβ to the OH group) giving a motif not seen previously in fluorofullerenes.

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More information

Published date: 2 June 2003
Keywords: Fullerenes, Fluoroxyfluorofullerene, Oxahomofluorofullerenol, Ethers, Fluorine NMR

Identifiers

Local EPrints ID: 26747
URI: http://eprints.soton.ac.uk/id/eprint/26747
ISSN: 0022-1139
PURE UUID: d89c01b8-2499-46af-8a40-d4145ad69f97

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Date deposited: 11 Apr 2006
Last modified: 08 Jan 2022 09:56

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Contributors

Author: A.D. Darwish
Author: A.K. Abdul-Sada
Author: A.G. Avent
Author: J.M. Street
Author: R. Taylor

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