Reversible Microwave-Assisted Cycloaddition of Aziridines to Carbon Nanotubes
- 7 November 2007
- journal article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 129 (47), 14580-14581
- https://doi.org/10.1021/ja077927k
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.Keywords
This publication has 23 references indexed in Scilit:
- Functionalization of Single-Walled Carbon Nanotubes and Fullerenes via a Dimethyl Acetylenedicarboxylate−4-Dimethylaminopyridine Zwitterion ApproachJournal of the American Chemical Society, 2007
- Functionalization of Single-Wall Carbon Nanotubes by Tandem High-Pressure/Cr(CO)6 Activation of Diels−Alder CycloadditionJournal of the American Chemical Society, 2006
- Microwave absorption by an array of carbon nanotubes: A phenomenological modelPhysical Review B, 2006
- Separation of Semiconducting from Metallic Carbon Nanotubes by Selective Functionalization with Azomethine YlidesJournal of the American Chemical Society, 2006
- Chemistry of Carbon NanotubesChemical Reviews, 2006
- Microwaves in organic synthesis. Thermal and non-thermal microwave effectsChemical Society Reviews, 2005
- Carbon NanotubesPublished by Wiley ,2004
- Sidewall Carboxylic Acid Functionalization of Single-Walled Carbon NanotubesJournal of the American Chemical Society, 2003
- Sidewall Functionalization of Single-Walled Carbon Nanotubes by Addition of DichlorocarbeneJournal of the American Chemical Society, 2003
- Functionalization of Single-Walled Carbon Nanotubes with (R-)Oxycarbonyl NitrenesJournal of the American Chemical Society, 2003