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Chemistry of Fullerene Epoxides: Synthesis, Structure, and Nucleophilic Substitution-Addition Reactivity
Organic Optoelectronics Laboratory, RIKEN, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan
Graduate School of Science and Engineering, Saitama University, 255 Shimoohkubo, Saitama 338-8570, Japan
FLOX Corporation, 2-3-13 Minami, Wako, Saitama 351-0104, Japan
Photovoltaic Materials Unit, National Institute for Materials Science, 1-2-1 Sengen, Tsukuba, Ibaraki 305-0047, Japan
* Author to whom correspondence should be addressed.
Received: 28 March 2012; in revised form: 14 May 2012 / Accepted: 16 May 2012 / Published: 25 May 2012
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.
Keywords: fullerene; epoxidation; regioselectivity; nucleophilic substitution; Lewis acid
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Tajima, Y.; Takeshi, K.; Shigemitsu, Y.; Numata, Y. Chemistry of Fullerene Epoxides: Synthesis, Structure, and Nucleophilic Substitution-Addition Reactivity. Molecules 2012, 17, 6395-6414.
Tajima Y, Takeshi K, Shigemitsu Y, Numata Y. Chemistry of Fullerene Epoxides: Synthesis, Structure, and Nucleophilic Substitution-Addition Reactivity. Molecules. 2012; 17(6):6395-6414.
Tajima, Yusuke; Takeshi, Kazumasa; Shigemitsu, Yasuo; Numata, Youhei. 2012. "Chemistry of Fullerene Epoxides: Synthesis, Structure, and Nucleophilic Substitution-Addition Reactivity." Molecules 17, no. 6: 6395-6414.