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

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.

SUBMITTER: Neri G

PROVIDER: S-EPMC5951103 | biostudies-literature | 2015 Dec

REPOSITORIES: biostudies-literature

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

Neri Giulia G Scala Angela A Fazio Enza E Mineo Placido G PG Rescifina Antonio A Piperno Anna A Grassi Giovanni G

Chemical science 20150826 12

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 inve ...[more]

PMID: 29861934

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Project description:Highly flexible and two-dimensional (2D) graphene oxide (GO) nanosheets have remained instrumental for developing different functional materials for practically relevant applications. In general, 2D GO is routinely assembled into different structures (i.e. layered, porous, etc.) for achieving desired properties. However, a facile approach for modifying GO nanosheets with (1) hierarchical topography and (2) desired chemistry is rare in the literature. In this report, adequate optimization of both hierarchical topography and low surface energy chemistry in a confined space (in the order of μm dimensions) of GO nanosheets is unprecedentedly carried out for achieving magnetically active and 2D 'confined-super-water-repellence'. A chemically reactive polymeric complex was covalently deposited on the GO-nanosheets through a facile 1,4-conjugate addition reaction for adopting a chemically reactive and hierarchically featured polymeric interface. Simultaneously, the deposition of iron oxide nanoparticles on the 2D-nanosheets rendered the entire material magnetically active. The post-covalent modification of these chemically/magnetically active and hierarchically featured GO-nanosheets with octadecylamine (ODA) yielded magnetically active and 2D 'confined-superhydrophobicity'. Further, this synthesized material was extended for addressing highly relevant and severe global challenges of 'oil-in-water' and 'water-in-oil' emulsion separation by either selective collection (with an efficiency of above 1000 wt%) of tiny oil-droplets from bulk water or forming magnetically active 'Pickering-type' aqueous droplets, respectively, under various practically relevant harsh conditions, including extremes of pH, salinity, surfactant contamination, etc. Further, appropriate functionalization of this chemically/magnetically active 2D nano-interface could be useful in developing functional interfaces for various applications related to energy, catalysis and healthcare.

Dataset Information

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

Publications

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

Similar Datasets

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