Fluorinated Fullerenes

Abstract

Recent developments in fluorination of fullerenes coupled with HPLC separation have permitted the isolation and subsequent structural characterisation of many derivatives, a number of which have novel and unexpected structures. The good solubility of fluorofullerenes, high reactivity towards nucleophiles and enhanced dienophilicity of the unsubstituted part of the cage, as a result of electron withdrawal by the fluorines, makes fluorofullerenes promising synthons. In particular that may have enhanced performance in donor-acceptor complexes with respect to bare fullerenes.

On the Importance of Halogen–Halogen Interactions in the Solid State of Fullerene Halides: A Combined Theoretical and Crystallographic Study

“…Related to this, the chlorination of C60 using iodine monochloride allowed the isolation of two fullerene chlorides, C60Cl6 [40] and C70Cl10 [41], characterized by NMR spectra. Finally, the fluorination of fullerenes using metal fluorides (among other fluorination agents) results in a wide range of adducts, from C60F2 to C60F48 [42][43][44][45]. Owing to their relatively high thermal stability, fluorofullerenes (contrary to chloro-and bromofullerenes) have been extensively investigated by electron impact (EI) mass spectrometry.…”

Defluorination-assisted nanotube-substitution reaction with ammonia gas for synthesis of nitrogen-doped single-walled carbon nanotubes

“…Those in the second group are graphite covalent compounds, in which the carbon atoms are covalently bonded to the fluorine atoms [16][17][18]. The carbon-fluorine bonds formed in the case of fullerenes [19][20][21] and SWCNTs [22][23][24][25][26][27][28] are covalent in nature, while those formed in the case of MWCNTs [29][30][31][32] are both covalent and ionic.…”

Elemental fluorine in organic chemistry (1997–2006)

“…This review will cover published literature concerning the use of elemental fluorine for the synthesis of carbon-fluorine bonds in organic systems over the period 1997-2006, updating our earlier review [8] on this subject in a similar format and complementing other recent discussions in this area [9][10][11]. The fluorination of fullerenes has been reviewed [12,13] and will not be discussed here whilst the chemistry of reagents that are synthesised from fluorine, such as reagents of the N-F class [6,14] and HOF [15], is also beyond the scope of this review.…”