Selective Functionalization of Graphene at Defect-Activated Sites by Arylazocarboxylic tert-Butyl Esters

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Details zur Publikation

Autor(en): Halbig CE, Lasch R, Krüll J, Pirzer A, Wang Z, Kirchhof JN, Bolotin KI, Heinrich M, Eigler S
Zeitschrift: Angewandte Chemie International Edition
Jahr der Veröffentlichung: 2019
Band: 58
Heftnummer: 11
Seitenbereich: 3599-3603
ISSN: 1433-7851
eISSN: 1521-3773


Abstract

The development of versatile functionalization concepts for graphene is currently in the focus of research. Upon oxo-functionalization of graphite, the full surface of graphene becomes accessible for C-C bond formation to introduce out-of-plane functionality. Herein, we present the arylation of graphene with arylazocarboxylic tert-butyl esters, which generates aryl radicals after activation with an acid. Surprisingly, the degree of functionalization is related to the concentration of lattice vacancy defects in the graphene material. Consequently, graphene materials that are free from lattice defects are not reactive. The reaction can be applied to graphene dispersed in solvents and leads to bitopic functionalization as well as monotopic functionalization when the graphene is deposited on surfaces. As the arylazocarboxylic tert-butyl ester moiety can be attached to various molecules, the presented method paves the way to functional graphene derivatives, with the density of defects determining the degree of functionalization.


FAU-Autoren / FAU-Herausgeber

Heinrich, Markus Prof. Dr.
Professur für Pharmazeutische Chemie
Krüll, Jasmin
Professur für Pharmazeutische Chemie
Lasch, Roman
Lehrstuhl für Pharmazeutische Chemie
Pirzer, Anna
Lehrstuhl für Pharmazeutische Chemie


Autor(en) der externen Einrichtung(en)
Freie Universität Berlin


Zitierweisen

APA:
Halbig, C.E., Lasch, R., Krüll, J., Pirzer, A., Wang, Z., Kirchhof, J.N.,... Eigler, S. (2019). Selective Functionalization of Graphene at Defect-Activated Sites by Arylazocarboxylic tert-Butyl Esters. Angewandte Chemie International Edition, 58(11), 3599-3603. https://dx.doi.org/10.1002/anie.201811192

MLA:
Halbig, Christian E., et al. "Selective Functionalization of Graphene at Defect-Activated Sites by Arylazocarboxylic tert-Butyl Esters." Angewandte Chemie International Edition 58.11 (2019): 3599-3603.

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Zuletzt aktualisiert 2019-20-03 um 13:08