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

Halbig CE, Lasch R, Krüll J, Pirzer A, Wang Z, Kirchhof JN, Bolotin KI, Heinrich M, Eigler S (2019)

Publication Type: Journal article

Publication year: 2019

Journal

Angewandte Chemie International Edition Wiley

Book Volume: 58

Pages Range: 3599-3603

Journal Issue: 11

DOI: 10.1002/anie.201811192

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.

Authors with CRIS profile

Roman Lasch Lehrstuhl für Pharmazeutische Chemie Jasmin Krüll Professur für Pharmazeutische Chemie Anna Pirzer Lehrstuhl für Pharmazeutische Chemie Markus Heinrich Professur für Pharmazeutische Chemie

Involved external institutions

Freie Universität Berlin DE Germany (DE)

How to cite

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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