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Diels–Alder reactions of graphene oxides: greatly enhanced chemical reactivity by oxygen-containing groups

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Abstract

Graphene oxides (GOs) or reduced GOs (rGOs) may offer extraordinary potential for chemical functionalization of graphene due to their unique electronic and structural properties. By means of dispersion-corrected density functional theory computations, we systematically investigated the Diels–Alder (DA) chemistry of GOs. Our computations showed that the dual nature of GOs as both a diene and a dienophile is stronger than that of pristine graphene. Interestingly, the interior bonds of a graphene surface modified by oxygen-containing groups could be functionalized by maleic anhydride (MA) and 2,3-dimethoxybutadiene (DMBD) through cycloaddition reactions, and the cycloaddition products of MA and DMBD are more favorable than the non-covalent complexes between these reagents and the GO surface. The feasibility of covalent functionalization of GOs as a diene and a dienophile strongly depends on the local structural environment of the oxygen groups, including the atomic arrangement and the number of these groups surrounding the reaction site. The exothermicities for (4+2) adducts of DMBD with GO are far larger than those of MA, which indicates that the dienophile character of the GO surface is stronger than its behavior as a diene.

Graphical abstract: Diels–Alder reactions of graphene oxides: greatly enhanced chemical reactivity by oxygen-containing groups

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Publication details

The article was received on 18 Feb 2017, accepted on 28 Mar 2017 and first published on 31 Mar 2017


Article type: Paper
DOI: 10.1039/C7CP01086A
Citation: Phys. Chem. Chem. Phys., 2017, Advance Article
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    Diels–Alder reactions of graphene oxides: greatly enhanced chemical reactivity by oxygen-containing groups

    S. Tang, W. Wu, L. Liu, Z. Cao, X. Wei and Z. Chen, Phys. Chem. Chem. Phys., 2017, Advance Article , DOI: 10.1039/C7CP01086A

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