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

Autor: Fensterbank H; Université de Versailles-Saint-Quentin-en-Yvelines , ILV, UMR-CNRS 8180, 45 avenue des Etats-Unis, 78035 Versailles Cedex, France., Baczko K; Université de Versailles-Saint-Quentin-en-Yvelines , ILV, UMR-CNRS 8180, 45 avenue des Etats-Unis, 78035 Versailles Cedex, France., Constant C; Université de Versailles-Saint-Quentin-en-Yvelines , ILV, UMR-CNRS 8180, 45 avenue des Etats-Unis, 78035 Versailles Cedex, France., Idttalbe N; Université de Versailles-Saint-Quentin-en-Yvelines , ILV, UMR-CNRS 8180, 45 avenue des Etats-Unis, 78035 Versailles Cedex, France., Bourdreux F; Université de Versailles-Saint-Quentin-en-Yvelines , ILV, UMR-CNRS 8180, 45 avenue des Etats-Unis, 78035 Versailles Cedex, France., Vallée A; Université de Versailles-Saint-Quentin-en-Yvelines , ILV, UMR-CNRS 8180, 45 avenue des Etats-Unis, 78035 Versailles Cedex, France., Goncalves AM; Université de Versailles-Saint-Quentin-en-Yvelines , ILV, UMR-CNRS 8180, 45 avenue des Etats-Unis, 78035 Versailles Cedex, France., Méallet-Renault R; Institut des Sciences Moléculaires d'Orsay (ISMO), CNRS, Université Paris-Sud, Université Paris-Saclay , F-91405 Orsay, France., Clavier G; P.P.S.M., ENS Cachan, UMR-CNRS 8531, Université Paris-Saclay , 61 Avenue du Président Wilson, 94235 Cachan Cedex, France., Wright K; Université de Versailles-Saint-Quentin-en-Yvelines , ILV, UMR-CNRS 8180, 45 avenue des Etats-Unis, 78035 Versailles Cedex, France., Allard E; Université de Versailles-Saint-Quentin-en-Yvelines , ILV, UMR-CNRS 8180, 45 avenue des Etats-Unis, 78035 Versailles Cedex, France.
Jazyk: angličtina
Zdroj: The Journal of organic chemistry [J Org Chem] 2016 Sep 16; Vol. 81 (18), pp. 8222-33. Date of Electronic Publication: 2016 Aug 26.
DOI: 10.1021/acs.joc.6b01277
Abstrakt: 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.
Databáze: MEDLINE
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