C60F18O: Isolation, spectroscopic characterisation and structural calculations

Formation, Isolation, and Spectroscopic Properties of Some Isomers of C60H38, C60H40, C60H42, and C60H44 − Analysis of the Effect of the Different Shapes of Various Helium‐Containing Hydrogenated Fullerenes on Their 3He Chemical Shifts

“…A similar increase in HPLC retention times with increasing polarity has been noted for another series of closely related fluorinated C 60 derivatives. [35,36] C 60 H 18 is isostructural with C 60 F 18 . [27,37] Calculations indicate that C 60 H 18 has a slightly less planar, slightly less aromatic ring surrounded by the C 18 H 18 crown.…”

Fullerene oxides and ozonides

“…Schuster et al [23] suggested that this photochemical synthesis proceeds via reaction of singlet molecular oxygen with the lowest triplet excited state of C 60 . A failed attempt was made to synthesize the [5,6]open oxidoannulene isomer by the photoxidation of C 60 in oxygenated benzene [24].…”

“…We choose to include here only such derivatives whose synthesis involves fullerene oxides or ozonides as starting materials. For example, C 60 F 18 O, which was obtained as a byproduct of the fluorination of C 60 with K 2 PtF 6 [6], is an oxygen-bearing fullerene that falls outside the scope of the present review.…”

“…For simplicity, we will refer here to compounds with formulas C m O n as C m -oxide (for n = 1), C m -dioxide (for n = 2) etc., and to C m (O 3 ) n compounds as C m -ozonides, C m -diozonides etc. When the -O-moiety of an oxide bridges a [6,6] C-C http://france.elsevier.com/direct/CRAS2C/ C. R. Chimie 9 (2006) [1107][1108][1109][1110][1111][1112][1113][1114][1115][1116] bond in the fullerene cage, the derivative will be called an epoxide to denote retention of the underlying C-C bond. Alternatively, when the oxygen atom bridges a [4,5] C-C bond, the underlying bond is weakened or broken to give an ether-like structure called an annulene.…”

Fluorinated Fullerenes

“…The 19 F NMR spectrum was consistent with either an epoxide or an ether, the former being assumed in view of the considerable evidence for the presence of epoxides (see above). [46] More recently, the single-crystal X-ray structure ( Figure 14) showed the oxide to be an ether (oxahomofullerene), [47] which is the first such fullerene species to be isolated; homofullerenes and azahomofullerenes, the CR and NR 2 analogues, have been isolated previously. [48] Figure 14.…”