Fluorographene Modified by Grignard Reagents: A Broad Range of Functional Nanomaterials

0475123 - ÚOCHB 2018 RIV DE eng J - Journal Article
Mazánek, V. - Libánská, A. - Šturala, J. - Bouša, D. - Sedmidubský, D. - Pumera, M. - Janoušek, Zbyněk - Plutnar, Jan - Sofer, Z.
Fluorographene Modified by Grignard Reagents: A Broad Range of Functional Nanomaterials.
Chemistry - A European Journal. Roč. 23, č. 8 (2017), s. 1956-1964. ISSN 0947-6539. E-ISSN 1521-3765
R&D Projects: GA ČR(CZ) GA15-09001S
Institutional support: RVO:61388963
Keywords : alkylation * click chemistry * fluorine * graphene * Grignard reagents
OECD category: Organic chemistry
Impact factor: 5.160, year: 2017

Fluorographene is the youngest stoichiometric derivative of graphene, hence, its reactivity is only poorly explored. Compared to graphene, the significantly higher reactivity of C-F bonds makes this material a suitable platform for a large number of chemical modifications. Fluorographene is also the only member of the halographene family that can be prepared in the stoichiometric composition (C1F1). Herein, the chemical modification of fluorographene with Grignard reagents, which are well known in organic synthesis for the formation of new C-C bonds, is presented. The reaction with alkyl magnesium bromides led to successful modification of fluorographene with ethyl, vinyl, ethynyl and propargyl groups. Chemical characterisation showed the presence of covalently bonded functional groups in a high concentration exceeding one functional group per C-6 motif. The reactivity of Grignard reagents with fluorographene decreased from ethyl to ethynyl. The terminal carbon-carbon triple bonds were used for click reactions with organic azides leading to the formation of triazole rings. These findings open up a broad spectrum of opportunities for simple and robust modification of graphene by chemical reactions proceeding at room temperature under mild conditions. These results have major application potential in sensing, biomedical and energy-related applications.
Permanent Link: http://hdl.handle.net/11104/0271983