Ozonolysis of [60]fullerene

Abstract

Ozonolysis of [60]fullerene (&) generates a mixture of the oxidized products having ketone, ester, and epoxide functionalities; an intermediate in this reaction can also transfer an oxygen to aromatic compounds to give normal and NIH-shifted phenols.

Ozone addition to C60 and C70 fullerenes: A DFT study

“…Comparison of the calculated activation enthalpies ( Table 3) makes clear that 1,2-addition is more favorable energetically and occurs without a barrier. This is in accordance with the experimental identification of [6.6] closed epoxide C 60 O among the products of the further primary ozone adduct decomposition [1,2].…”

“…Heymann et al [1] have detected the primary ozonide (PO) C 60 O 3 as a product of initial ozone addition, which has been isolated with low-temperature highperformance liquid chromatography. A study of its decomposition with UV-visible spectroscopy and luminescent methods has shown that C 60 O 3 eliminates O 2 molecule, producing the fullerene epoxide C 60 O [1] (other investigations have shown that the carbonyl derivatives are also produced during the PO conversion [2,3]). Those experimental data were sufficient to determine PO's empirical formula while its structural peculiarities have not been clear.…”

Beyond nC60: strategies for identification of transformation products of fullerene oxidation in aquatic and biological samples

“…In addition to phototransformation, extensive chemical transformations of C 60 occur in the presence of ozone [82]. Ozonation of n C 60 resulted in significant transformation within hours, as demonstrated by a reduction in fullerene-specific absorbance peaks in UV–visible measurements (>90 % after 90 h).…”

Fullerene oxides and ozonides

“…Here we distinguish these by the wavelengths (in nm) of their characteristic near-UV absorption maxima: C 60 [34]), are diepoxides, that C 60 O 2 (314) is probably another diepoxide, and that the remaining isomers are either diannulenes or epoxyannulenes [26,34,42,59,69,72,94,103,105].…”