Th-C60F24

J Am Chem Soc. 2004 Feb 18;126(6):1618-9. doi: 10.1021/ja039361f.

Abstract

The regioselective fluorination of Th-C60Br24 with XeF2 in anhydrous HF at 25 degrees C produced Th-C60F24, which is isostructural with Th-C60Br24. The compound, the first example of a fluorofullerene with a noncontiguous pattern of F-bearing sp3 C atoms, was characterized by EI and ESI mass spectrometry and by 19F NMR (single resonance at delta -144 for all 24 F atoms), 13C NMR (two resonances at delta 145.9 (C=C) and delta 83.5 (C-F; JCF = 212 Hz), and FTIR spectroscopy. DFT calculations revealed that at least two other isomers of C60F24 are more stable than Th-C60F24 by >/=280 kJ mol-1, demonstrating that Th-C60F24 is a kinetically stable fluorofullerene.