Isolation and characterisation of forty-nine fluorinated derivatives of 70 fullerene

Taylor, R., Abdul-Sada, A. K., Boltalina, O. V. and Street, J. R. (2000) Isolation and characterisation of forty-nine fluorinated derivatives of 70 fullerene. Journal of the Chemical Society, Perkin Transactions 2, (5), 1013-1021. (doi:10.1039/a909490c).

Abstract

From 100 mg of the product of fluorination of [70]fullerene with MnF3 at 450 degrees C at ca. 0.1 bar, we have isolated forty-nine components by HPLC and characterised them by mass spectrometry, together with IR and both 1D and 2D F-19 NMR spectroscopy (where quantities permitted). The separation was carried out using a 4.6 mm diameter Cosmosil 'Buckyprep' column with elution by either toluene, various toluene-heptane mixtures, or heptane, and entailed some 950 manual runs. The products comprise numerous isomers of C70F44, C70F42, C70F40, C70F38, C70F36, C70F34, C70F40O, C70F38O, C70F36O, C70F36O, C70F35O . OH, C70F37. O . OH, and C70F34O3. A component that eluted just before one of the C70F38 isomers, was indicated by mass spectrometry to be C70F37 but is probably an exceptionally stable fragment produced by degradation of an oxide precursor, a view supported by temperature-degradation studies. One each of C70F42, C70F38, C70F36 isomers, at least two C70F40 isomers, and C70F34O3 have either C-s or C-2 symmetry all the other compounds have C-1 symmetry The main components are two C70F38 isomers (nos. 8 and 14). Other components detected in trace amounts were C70F39O . OH, the poly-epoxides C70F36O, C70F36O2 and C70F36O3 and the poly-epoxy dihydroxides, C70F30O2(OH)(2), C70F30O3(OH)(2), and C70F30O4(OH)(2).

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