Issue 12, 2015
From the journal:

Chemical Science

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

Giulia Neri,a   Angela Scala,a   Enza Fazio,b   Placido G. Mineo, ORCID logo c   Antonio Rescifina, ORCID logo d   Anna Piperno ORCID logo *a  and  Giovanni Grassia  

* Corresponding authors

a Dipartimento di Scienze Chimiche, Università di Messina, Viale Ferdinando Stagno D'Alcontres 31, 98166 Messina, Italy
E-mail: apiperno@unime.it
Fax: +39 090393897
Tel: +39 0906765173

b Dipartimento di Fisica e di Scienze della Terra, Università di Messina, V.le F. Stagno d'Alcontres 31, 98166 Messina, Italy

c Dipartimento di Scienze Chimiche, Università di Catania, V.le A. Doria 6, 95125 Catania, Italy

d Dipartimento di Scienze del Farmaco, Università di Catania, V.le A. Doria 6, 95125 Catania, Italy

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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Article information

DOI
https://doi.org/10.1039/C5SC02576A
Article type
Edge Article
Submitted
16 Jul 2015
Accepted
24 Aug 2015
First published
26 Aug 2015
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2015,6, 6961-6970

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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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