Definitive proof of graphene hydrogenation by Clemmensen reduction: Use of deuterium labeling

Zdeněk Sofer, Ondřej Jankovský, Alena Libánská, Petr Šimek, Michal Nováček, David Sedmidubský, Anna MacKová, Romana Mikšová, Martin Pumera

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

Graphane is one of the most intensively studied derivatives of graphene. Here we demonstrate the evaluation of exact degree of graphene hydrogenation using the Clemmensen reduction reaction and deuterium labeling. The Clemmensen reduction reaction is based on application of zinc in an acid environment. It effectively reduces various functional groups (like ketones) present in graphite oxide. However, the mechanism of reduction is still unknown and elusive. Here we bring a major insight into the mechanisms of the Clemmensen reduction via deuterium labeling and the topochemical approach applied on graphite oxide. The use of deuterated reactants and the exact measurement of deuterium concentration in reduced/hydrogenated graphene by nuclear methods can be used for accurate estimation of C-H bond abundance in graphene. Various topochemical configurations of experiments showed that the reduction of a ketonic group proceeds in contact with the zinc metal by a carbenoid mechanism. Our results showed that the application of nuclear methods of isotope analysis in combination with deuterium labeling represents a very effective tool for investigation of graphene based materials. Our results demonstrate that graphene based materials can also be effectively used for the investigation of organic reaction mechanisms, because the robust structure of graphene allows the use of various spectroscopic techniques which could not be applied on small organic molecules.

Original languageEnglish
Pages (from-to)10535-10543
Number of pages9
JournalNanoscale
Volume7
Issue number23
DOIs
Publication statusPublished - 2015 Jun 21

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Graphite
Deuterium
Graphene
Labeling
Hydrogenation
Zinc
Oxides
Ketones
Functional groups
Isotopes
Derivatives
Molecules
Metals
Acids

All Science Journal Classification (ASJC) codes

  • Materials Science(all)

Cite this

Sofer, Z., Jankovský, O., Libánská, A., Šimek, P., Nováček, M., Sedmidubský, D., ... Pumera, M. (2015). Definitive proof of graphene hydrogenation by Clemmensen reduction: Use of deuterium labeling. Nanoscale, 7(23), 10535-10543. https://doi.org/10.1039/c5nr01356a
Sofer, Zdeněk ; Jankovský, Ondřej ; Libánská, Alena ; Šimek, Petr ; Nováček, Michal ; Sedmidubský, David ; MacKová, Anna ; Mikšová, Romana ; Pumera, Martin. / Definitive proof of graphene hydrogenation by Clemmensen reduction : Use of deuterium labeling. In: Nanoscale. 2015 ; Vol. 7, No. 23. pp. 10535-10543.
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Sofer, Z, Jankovský, O, Libánská, A, Šimek, P, Nováček, M, Sedmidubský, D, MacKová, A, Mikšová, R & Pumera, M 2015, 'Definitive proof of graphene hydrogenation by Clemmensen reduction: Use of deuterium labeling', Nanoscale, vol. 7, no. 23, pp. 10535-10543. https://doi.org/10.1039/c5nr01356a

Definitive proof of graphene hydrogenation by Clemmensen reduction : Use of deuterium labeling. / Sofer, Zdeněk; Jankovský, Ondřej; Libánská, Alena; Šimek, Petr; Nováček, Michal; Sedmidubský, David; MacKová, Anna; Mikšová, Romana; Pumera, Martin.

In: Nanoscale, Vol. 7, No. 23, 21.06.2015, p. 10535-10543.

Research output: Contribution to journalArticle

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AU - Libánská, Alena

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AU - Nováček, Michal

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AU - MacKová, Anna

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AU - Pumera, Martin

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Sofer Z, Jankovský O, Libánská A, Šimek P, Nováček M, Sedmidubský D et al. Definitive proof of graphene hydrogenation by Clemmensen reduction: Use of deuterium labeling. Nanoscale. 2015 Jun 21;7(23):10535-10543. https://doi.org/10.1039/c5nr01356a