Reversible microwave-assisted cycloaddition of aziridines to carbon nanotubes.
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.
Brunetti
Fulvio G
FG
Dipartimento di Scienze Farmaceutiche, Università degli Studi di Trieste, Piazzale Europa 1, 34127 Trieste, Italy.
Herrero
M Antonia
MA
Muñoz
Juan de M
Jde M
Giordani
Silvia
S
Díaz-Ortiz
Angel
A
Filippone
Salvatore
S
Ruaro
Giorgio
G
Meneghetti
Moreno
M
Prato
Maurizio
M
Vázquez
Ester
E
D001388:Aziridines / Q000737:chemistry*; D008872:Microwaves; D015394:Molecular Structure; D037742:Nanotubes, Carbon / Q000737:chemistry*; D013059:Spectrum Analysis, Raman
D001388:Aziridines; D037742:Nanotubes, Carbon