J. Am. Chem. Soc., 129 (47), 14580 -14581, 2007. 10.1021/ja077927k S0002-7863(07)07927-9
Web Release Date: November 7, 2007

Copyright © 2007 American Chemical Society

Reversible Microwave-Assisted Cycloaddition of Aziridines to Carbon Nanotubes

Fulvio G. Brunetti,# M. Antonia Herrero,# Juan de M. Muñoz,# Silvia Giordani, Angel Díaz-Ortiz,# Salvatore Filippone, Giorgio Ruaro, Moreno Meneghetti, Maurizio Prato,* and Ester Vzquez*#

Dipartimento di Scienze Farmaceutiche, Università degli Studi di Trieste, Piazzale Europa 1, 34127 Trieste, Italy, Departamento de Química Orgnica, Facultad de Química, Universidad de Castilla-La Mancha, 13071 Ciudad Real, Spain, Dipartimento di Scienze Chimiche, Università di Padova, Via Marzolo 1, 35131 Padova, Italy, and Departamento de Química Orgnica I, Facultad de Químicas, Universidad Complutense de Madrid, 28040 Madrid, Spain

prato@units.it; ester.vazquez@uclm.es

Received October 16, 2007

Abstract:

We report a new approach that uses microwaves to rapidly functionalize carbon nanotubes by using 1,3-dipolar cycloaddition of aziridines, well-known precursors to azomethine ylides, in solvent-free conditions. The efficiency of our microwave-mediated protocol is confirmed by comparison to a similar protocol in classical conditions for the azomethine ylides in DMF. Under these latter conditions, the reaction proceeds in 5 days (against 1 h under microwave irradiation), and the functionalization degree is much lower, as confirmed by thermogravimetric analysis and Raman spectroscopy. With our procedure, we easily scale-up the reaction up to 250 mg of functionalized MWNT in 1 h. We also provide an indirect proof of the covalent sidewall functionalization of the tubes.

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