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Issue 12, 2015
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Repurposing of oxazolone chemistry: gaining access to functionalized graphene nanosheets in a top-down approach from graphite

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Abstract

Solvent-free 1,3-dipolar cycloaddition (1,3-DC) reactions between graphite flakes and mesoionic oxazolones were carried out by heating the resulting solid mixture at mild temperatures (70–120 °C). The direct functionalization and delamination of graphite flakes into few layers of graphene nanosheets was confirmed by micro-Raman and X-ray photoelectron spectroscopies, scanning transmission electron microscopy and thermogravimetric analysis. The 1,3-DC reactions of mesoionic dipoles have been investigated with density functional theory to model graphene, exploring three different pathways: center, corner and edge. These theoretical calculations highlighted that the 1,3-DC reaction can proceed both through a concerted mechanism competing with a stepwise one involving a zwitterionic intermediate. The irreversible decarboxylation inherent in the last step justifies the high degree of functionalization experimentally observed, representing the driving force of the process.

Graphical abstract: Repurposing of oxazolone chemistry: gaining access to functionalized graphene nanosheets in a top-down approach from graphite

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Publication details

The article was received on 16 Jul 2015, accepted on 24 Aug 2015 and first published on 26 Aug 2015


Article type: Edge Article
DOI: 10.1039/C5SC02576A
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Citation: Chem. Sci., 2015,6, 6961-6970
  • Open access: Creative Commons BY-NC license
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    Repurposing of oxazolone chemistry: gaining access to functionalized graphene nanosheets in a top-down approach from graphite

    G. Neri, A. Scala, E. Fazio, P. G. Mineo, A. Rescifina, A. Piperno and G. Grassi, Chem. Sci., 2015, 6, 6961
    DOI: 10.1039/C5SC02576A

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