Bisaziridine Tetracarboxylates as Building Blocks in the Stereoselective Synthesis of C-60-Fullerene Diads and Dumbbell-like Bis-C-60-fullerene Triads

Abstract

The synthesis of alkoxycarbonyl-substituted bisaziridines with the two aziridine units connected by conjugated p-phenylene, partly conjugated 1,1'-biphenyl-4,4'-diyl, and non-conjugated 4,4'-methylenediphenyl linkers was developed. The reaction of azomethine ylides derived from the bisaziridines with fullerene C-60 was optimized and used for the stereoselective preparation of both the monoadducts (C-60-linker-aziridine dicarboxylate), and the dumbbell bisadducts (C-60-linker-C-60). The reasons for the observed selectivity of the azomethine ylide formation and cycloaddition were theoretically studied at the DFT B3LYP/6-31G(d) level or at the ONIOM B3LYP/6-31G(d):B3LYP/STO-3G level for fullerene-containing molecules.