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Título: | Grafting of adipic anhydride to carbon nanotubes through a Diels-Alder cycloaddition/oxidation cascade reaction |
Autor: | Araújo, Rui Filipe; Proença, Maria Fernanda; Silva, Carlos Jorge; Castro, Tarsila G.; Melle-Franco, Manuel; Paiva, Maria Conceição; Villar Rodil, Silvia CSIC ORCID ; Díez Tascón, Juan Manuel CSIC ORCID | Fecha de publicación: | 10-nov-2015 | Editor: | Elsevier | Citación: | Carbon 98: 421-431 (2016) | Resumen: | Different reactions have been reported for the successful functionalization of carbon nanotubes (CNT). The Diels-Alder cycloaddition is recognized as a plausible chemical approach, but few reports are known where this strategy has been used. In this study, the functionalization was performed by 1,3-butadiene generated from 3-sulfolene under heating conditions in diglyme. This simple and easily scalable method resulted in functionalized CNT with mass losses of 10–23% by thermogravimetric analysis (nitrogen atmosphere). The functionalization was also supported by acid-base titration, elemental analysis, temperature programmed desorption and X-ray photoelectron spectroscopy. The high content in oxygen detected on the CNT surface was assigned to anhydride formation due to a cascade oxidation of the alkene groups generated in the cycloaddition reaction. The complete evolution of the alkene leads to a grafting density of 4.2 mmol g−1 for the anhydride moiety. Ab-initio calculations in CNT model systems indicate that the Diels-Alder addition of butadiene is a feasible process and that subsequent oxidation reactions may result in the formation of the anhydride moiety. The presence of the anhydride group is a valuable asset for grafting a multitude of complex molecules, namely through the nucleophilic addition of amines. | Versión del editor: | https://doi.org/10.1016/j.carbon.2015.11.004 | URI: | http://hdl.handle.net/10261/182445 | DOI: | 10.1016/j.carbon.2015.11.004 | ISSN: | 0008-6223 |
Aparece en las colecciones: | (INCAR) Artículos |
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Grafting_anhydrides_Araujo.pdf | 891,64 kB | Adobe PDF | Visualizar/Abrir | |
Grafting_anhydrides_Araujo_SI.pdf | Supplementary Information | 743,16 kB | Adobe PDF | Visualizar/Abrir |
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