Synthesis of Dumbbell-like Amine-Functionalized Bis-C60 Fullerene

Amol Balu Atar presents a photochemical synthesis of dumbbell-like functionalized bis-C60 fullerene.

A Photocatalyst-Free, SET-Mediated Photochemical Approach for the Synthesis of Dumbbell-Like Amine-Functionalized Bis-C60 Fullerene through C–C Bond Formation: A. B. Atar

Synlett 2019, 30, 1462–1468

Photo-induced single-electron-transfer (SET) reactions performed without using a photocatalyst have become an attractive methodology for the preparation of substituted fullerenes. The creation of a C–C bond through a photoinduced SET reaction requires the formation of a radical ion pair in which the electron donor unit, such as a tertiary amine, and the electron acceptor, i.e. a fullerene, form a complex organic molecule. In the framework of a research program concerning the development of new C–C and C–N bond forming reactions for the synthesis of compounds with two bis-α-silyl tertiary benzyl amine functions connected by an aliphatic linker, Dr. Amol Balu Atar from Sejong University (Seoul, South Korea) recently reported a strategy which allows for the construction of amine-functionalized bis-C60 fullerenes.

Dr. Atar said: “The present method describes a novel method for the synthesis of dumbbell-like amine-functionalized bis-C60 fullerene from simple bis-α-silyl tertiary benzyl amines and C60 fullerene. The photoreactions between bis-α-silyl tertiary benzyl amines and C60 furnished single-bonded bis-aminomethyl-1,2-dihydrofullerenes and double-bonded 1,2,5-trisubstituted bis-fulleropyrrolidines through 1,3-dipolar cycloaddition reactions of azomethine ylides under milder conditions.” 

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