Abstract
Fullerene epoxides, C60On, having epoxide groups directly attached to the fullerene cage, constitute an interesting class of fullerene derivatives. In particular, the chemical transformations of fullerene epoxides are expected to play an important role in the development of functionalized fullerenes. This is because such transformations can readily afford a variety of mono- or polyfunctionalized fullerene derivatives while conserving the epoxy ring arrangement on the fullerene surface, as seen in representative regioisomeric fullerene polyepoxides. The first part of this review addresses the synthesis and structural characterization of fullerene epoxides. The formation of fullerene epoxides through different oxidation reactions is then explored. Adequate characterization of the isolated fullerene epoxides was achieved by concerted use of NMR and LC-MS techniques. The second part of this review addresses the substitution of fullerene epoxides in the presence of a Lewis acid catalyst. Most major substitution products have been isolated as pure compounds and their structures established through spectroscopic methods. The correlation between the structure of the substitution product and the oxygenation pattern of the starting materials allows elucidation of the mechanistic features of this transformation. This approach promises to lead to rigorous regioselective production of various fullerene derivatives for a wide range of applications.
Highlights
Since the first detection of fullerene epoxides via mass spectrometry in a fullerene mixture generated by the arc discharge of graphite in 1991, many studies on fullerene oxides have been performed for the purpose of developing new materials
We have found that the acetalization reactions of fullerene epoxide 1a with various carbonyl compounds occur in the presence of a Lewis acid catalyst, an ionexchange resin such as Amberlite, and a clay mineral such as montmorillonite to afford the corresponding 1,3-dioxolane derivatives in very high yields (Table 2) [9,22]
This review presents an overview of our works on the nature and chemical transformation of fullerene epoxides
Summary
Since the first detection of fullerene epoxides via mass spectrometry in a fullerene mixture generated by the arc discharge of graphite in 1991, many studies on fullerene oxides have been performed for the purpose of developing new materials. We demonstrated experimentally the regioselectivity of the epoxidation of C60 by means of the identification of products from each oxidation of the isolated isomers. Reaction of C60O with benzaldehyde in the presence of a Lewis acid led to the formation of a 1,3-dioxolane derivative of C60 in high yield. This implies the possibility of other nucleophilic substitutions of the epoxy rings on a fullerene cage. The recent development of large-scale production techniques for fullerene epoxide [12] prompted us to develop a new methodology to synthesize polyfunctionalized fullerene derivatives by means of efficient chemical transformation of regioisomerically pure fullerene polyepoxides. The direct substitution of epoxide oxygen atoms on the fullerene epoxide—a versatile and advantageous synthetic methodology we report here—provides highly regioselective access to a variety of fullerene adducts
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