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Sequential Copper-Catalyzed Alkyne-Azide Cycloaddition and Thiol-Maleimide Addition for the Synthesis of Photo- and/or Electroactive Fullerodendrimers and Cysteine-Functionalized Fullerene Derivatives

Fensterbank, H; Baczko, K; Constant, C; Idttalbe, N; Bourdreux, Fl; Vallee, A; Goncalves, A-M; Meallet-Renault, R; Clavier, G; Wright, K; Allard, E, JOURNAL OF ORGANIC CHEMISTRY, 2016, 81, 8222-8233

In this study, the functionalization of a fullerene building block in a stepwise process by means of the copper-catalyzed alkyne–azide cycloaddition (CuAAC) and thiol-maleimide reactions is reported. Grafting of the fullerene platform with a variety of azido derivatives, including Bodipy, pyrene and ferrocene, was carried out first. These fullerene compounds were then reacted with thiol derivatives to yield sophisticated structures comprising photo- and/or electroactive fullerodendrimers and cysteine-functionalized fullerene assemblies. This strategy, which combines the CuAAC and thiol-maleimide processes, could become more widely adopted in the field of fullerene chemistry.

Type :

Publication

Dates :

Paru le 16 septembre 2016

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DOI: 10.1021/acs.joc.6b01277