Volume 22, Issue 17 p. 5849-5852
Communication

New Insights into the Diels–Alder Reaction of Graphene Oxide

Patrick P. Brisebois

Patrick P. Brisebois

Department of Chemistry, UQAM/NanoQAM-CQMF, Montreal, Quebec, H3C 3P8 Canada

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Dr. Christian Kuss

Dr. Christian Kuss

Department of Chemistry, UQAM/NanoQAM-CQMF, Montreal, Quebec, H3C 3P8 Canada

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Dr. Steen B. Schougaard

Dr. Steen B. Schougaard

Department of Chemistry, UQAM/NanoQAM-CQMF, Montreal, Quebec, H3C 3P8 Canada

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Dr. Ricardo Izquierdo

Dr. Ricardo Izquierdo

Department of informatics, UQAM/CoFaMic-ReSMiQ, Montreal, Quebec, H3C 3P8 Canada

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Prof. Mohamed Siaj

Corresponding Author

Prof. Mohamed Siaj

Department of Chemistry, UQAM/NanoQAM-CQMF, Montreal, Quebec, H3C 3P8 Canada

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First published: 08 March 2016
Citations: 41

Graphical Abstract

Carbon frameworks: A Diels–Alder reaction with graphene oxide (GO) as the diene source and maleic anhydride as the dienophile has been outlined, thereby proving the presence of a cis diene on the graphene oxide framework. This reaction provides fundamental information for understanding the exact structure and chemical nature of graphene oxide.

Abstract

Graphene oxide is regarded as a major precursor for graphene-based materials. The development of graphene oxide based derivatives with new functionalities requires a thorough understanding of its chemical reactivity, especially for canonical synthetic methods such as the Diels–Alder cycloaddition. The Diels–Alder reaction has been successfully extended with graphene oxide as a source of diene by using maleic anhydride as a dienophile, thereby outlining the presence of the cis diene present in the graphene oxide framework. This reaction provides fundamental information for understanding the exact structure and chemical nature of graphene oxide. On the basis of high-resolution 13C-SS NMR spectra, we show evidence for the formation of new sp3 carbon centers covalently bonded to graphene oxide following hydrolysis of the reaction product. DFT calculations are also used to show that the presence of a cis dihydroxyl and C vacancy on the surface of graphene oxide are promoting the reaction with significant negative reaction enthalpies.