Synthesis of C60 Derivatives

We synthesized eight C60 derivatives: (I) N-[4-{endo-methyl(trioxyethylene) oxycarbonyl}phenyl]azafullerene (C60NEO3), (II) N-[4-(1-naphthyl)iminocarbo-nyl]phenylazafullerene (C60NNp), (III) N-[4-(4'-phenoxy)phenyliminocarbonyl] phenylazafullerene (C60N^O^), (IV) N-[4-{endo-methyl(trioxyethylene)oxycarbonyl} phenyl]azafullerene (double adduct) [C60(NEO3)2], (V) diphenylmethanofullerene (C60C^2), (VI) bis(p-methoxyphenyl)methanofullerene (C60CMO^2), (VII) diphenylmethanofullerene (double adduct) [C60(C^2)2], (VIII) bis(p-methoxyphenyl) methanofullerene (double adduct) [C60(CMO^2)2].

The molecular structure of derivatives is depicted in Fig. 9.31 . The derivatives are grouped into two types: phenylazafullerene and methanofullerene, where the former includes derivatives (I), (II), (III), and (IV) and the latter derivatives (V), (VI), (VII), and (VIII). We selected these two types of derivatives because of the ease of their synthesis. The derivatives of the same type can be synthesized using basically the same process. Here, we describe the synthesis of (I) and (V) as examples of phenylazafullerene [ 27] and methanofullerene derivatives [ 28], [ 29]. Figures 9.32 and 9.33 outline the synthesis processes.

C60NEO3 (I)

N-^D^C00(CH2CH20)3CHs

C60NNp (II)

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