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Vacchi IA, Spinato C, Raya J, et al. Chemical reactivity of graphene oxide towards amines elucidated by solid-state NMR. Nanoscale. 2016;8(28):13714-13721doi: 10.1039/c6nr03846h.
Vacchi, I. A., Spinato, C., Raya, J., Bianco, A., & Ménard-Moyon, C. (2016). Chemical reactivity of graphene oxide towards amines elucidated by solid-state NMR. Nanoscale, 8(28), 13714-13721. https://doi.org/10.1039/c6nr03846h
Vacchi, Isabella A, et al. "Chemical reactivity of graphene oxide towards amines elucidated by solid-state NMR." Nanoscale vol. 8,28 (2016): 13714-13721. doi: https://doi.org/10.1039/c6nr03846h
Vacchi IA, Spinato C, Raya J, Bianco A, Ménard-Moyon C. Chemical reactivity of graphene oxide towards amines elucidated by solid-state NMR. Nanoscale. 2016 Jul 14;8(28):13714-13721. doi: 10.1039/c6nr03846h. PMID: 27411370.
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Nanoscale. 2016 Jul 14;8(28):13714-13721. doi: 10.1039/c6nr03846h.

Chemical reactivity of graphene oxide towards amines elucidated by solid-state NMR.

Nanoscale

Isabella A Vacchi, Cinzia Spinato, Jésus Raya, Alberto Bianco, Cécilia Ménard-Moyon

Affiliations

  1. CNRS, Institut de Biologie Moléculaire et Cellulaire, Immunopathologie et Chimie Thérapeutique, 67000 Strasbourg, France. [email protected] [email protected].
  2. Membrane Biophysics and NMR, Institute of Chemistry, UMR 7177, University of Strasbourg, Strasbourg, France.

PMID: 27411370 DOI: 10.1039/c6nr03846h

Abstract

Graphene oxide (GO) is an attractive nanomaterial for many applications. Controlling the functionalization of GO is essential for the design of graphene-based conjugates with novel properties. But, the chemical composition of GO has not been fully elucidated yet. Due to the high reactivity of the oxygenated moieties, mainly epoxy, hydroxyl and carboxyl groups, several derivatization reactions may occur concomitantly. The reactivity of GO with amine derivatives has been exploited in the literature to design graphene-based conjugates, mainly through amidation. However, in this study we undoubtedly demonstrate using magic angle spinning (MAS) solid-state NMR that the reaction between GO and amine functions occurs via ring opening of the epoxides, and not by amidation. We also prove that there is a negligible amount of carboxylic acid groups in two GO samples obtained by a different synthesis process, hence eliminating the possibility of amidation reactions with amine derivatives. This work brings additional insights into the chemical reactivity of GO, which is fundamental to control its functionalization, and highlights the major role of MAS NMR spectroscopy for a comprehensive characterization of derivatized GO.

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