Synthesis of Extended Fullerenyl Cations and Development of Their Functional Monolayers

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1) Generation and Observation of a Alkylated C_<70> CationFullerenol Cl_2CH-C_<70>-OH was synthesized regioselectively. The first alkylated C_<70> cation, Cl_2CH-C_<70>^+ could be generated by the ionization of this fullerenol in CF_3SO_3H. The free energy of ionization, evaluated by the rate study of the S_N1 solvolysis of chloride Cl_2CH-C_<70>-Cl, revealed that cation Cl_2CH-C_<70>^+ has a thermodynamic stability that is almost equal to that of the corresponding C_<60> cation Cl_2CH-C_<60>^+.2) Generation and Observation of Methylated C_<60> CationThe methylated C_<60> cation (CH_3-C_<60>^+), most simple alkylated fullerenyl cation, was successfully generated by treating fullerenol CH_3-C_<60>-OH with CF_3SO_3H, and was observed by NMR and vis-NIR spectroscopy.3) Isolation of Alkylated a C_<60> CationAlkylated C_<60> cations could be also generated in CH_2Cl_2, a neutral organic solvent. Furthermore, a salt, ClCH_2-C_<60>^+ SbCl_6^-, could be isolated as solid by precipitating this salt by the addition of CS_2 to the CH_2Cl_2 solution.4) Formation of a Monolayer on Silica using Alkylated C_<60> CationMonolayer of ClCH_2-C_<60>-O- group could be formed by treating the surface of a silicone wafer or silica with a CH_2Cl_2 solution of chloride ClCH_2-C_<60>-Cl. The high surface coverage of this monolayer (6 nm^2/molec) was demonstrated by ellipsometry and absorption spectrometry.