Bisaziridine tetracarboxylates as building blocks in the stereoselective synthesis of C60-fullerene diads and dumbbell-like bis-C60-fullerene triads |
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Authors: | Konev Alexander S Khlebnikov Alexander F Frauendorf Holm |
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Affiliation: | Department of Chemistry, Saint Petersburg State University, Universitetskii pr. 26, 198504 St. Petersburg, Russia. |
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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 nonconjugated 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. |
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