Addition reactions and other chemical modifications of fullerenes easily produce fullerene derivatives. Precise structure analyses of these derivatives are possible because they are molecular species. Non-derivatized fullerenes are poorly soluble in similarity to the other nanocarbon materials. However, we can introduce soluble functional groups to form solution-processible electronic materials. Phenyl-C61-butyric acid methyl ester ([60]PCBM) and indene-C60 bisadduct (ICBA) are useful organic semiconductors for fabricating a solution-processible electronic device.5,6) These fullerene derivatives are n-type organic semiconductors for organic photovoltaics (OPV) by mixing with a p-type conjugated polymer.7) An application of a fullerene derivative for organic transistors was also reported.8) A complexation of C60 with tetrakis(dimethylamino)ethylene (TDAE) gives a charge transfer complex (TDAE-C60), which is an organic magnet at low temperature.9)
Although a chemical modification of the outer surface of fullerene provides PCBM or ICBA, we can introduce a small component to the inner side of fullerene. For instance, fullerenes can encapsulate a metal atom on the inner side, when the fullerenes are produced in the presence of the metal. This is the so-called metal-encapsulated fullerene described as MC60. The encapsulation modifies the electronic state10) and chemical reactivity of fullerene.11) On the other hand, water-encapsulated fullerene (H2OC60) was also reported. A publication described that an organic synthetic procedure gave open-caged C60 which could then encapsulate one water molecule. A following chemical modification could close the cage to from water-encapsulated fullerene H2OC60.12)
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