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Abstract
Chemical functionalizations of an endohedral metallofullerene, La2@Ih-C80, and an empty fullerene, C60, are demonstrated using organosulfur compounds. A novel donor–acceptor system of La2@Ih–C80-exTTF (3) synthesized using the Prato reaction shows photo-induced intramolecular charge separation. On the other hand, the photoreaction of C60 with N-p-toluenesulfonyl sulfilimine affords N-tosyl-1,2-aziridinofullerene (5). The first reversible interconversion of 1,2-aziridinofullerene and 1,6-azafulleroid was found for mono-substituted fullerenes by thermal rearrangement of 5 to 6. S,S-Diphenylsulfilimines (7) with an electron-donating group on the N atom reacts with C60 to afford corresponding aziridinofullerenes (8–10) regioselectively.
Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.
Acknowledgments
Financial support from a Grant-in-Aid for Scientific Research on Innovation Areas (No. 20108001, “pi-Space”); a Grant-in-Aid for Scientific Research (A) (No. 20245006), The Next Generation Super Computing Project (Nanoscience Project); Nanotechnology Support Project; and Grant-in-Aid for Scientific Research on Priority Area (Nos. 20036008, 20038007, 20045002) from the Ministry of Education, Culture, Sports, Science, and Technology of Japan is acknowledged.
