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Issue 24, 2010
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Azobenzeneversus3,3′,5,5′-tetra-tert-butyl-azobenzene (TBA) at Au(111): characterizing the role of spacer groups

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Abstract

We present large-scale density-functional theory (DFT) calculations and temperature programmed desorption measurements to characterize the structural, energetic and vibrational properties of the functionalized molecular switch 3,3′,5,5′-tetra-tert-butyl-azobenzene (TBA) adsorbed at Au(111). Particular emphasis is placed on exploring the accuracy of the semi-empirical dispersion correction approach to semi-local DFT (DFT-D) in accounting for the substantial van der Waals component in the surface bonding. In line with previous findings for benzene and pure azobenzene at coinage metal surfaces, DFT-D significantly overbinds the molecule, but seems to yield an accurate adsorption geometry as far as can be judged from the experimental data. Comparing the trans adsorption geometry of TBA and azobenzene at Au(111) reveals a remarkable insensitivity of the structural and vibrational properties of the –N[double bond, length as m-dash]N– moiety. This questions the established view of the role of the bulky tert-butyl-spacer groups for the switching of TBA in terms of a mere geometric decoupling of the photochemically active diazo-bridge from the gold substrate.

Graphical abstract: Azobenzene versus 3,3′,5,5′-tetra-tert-butyl-azobenzene (TBA) at Au(111): characterizing the role of spacer groups

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Article information


Submitted
29 Jan 2010
Accepted
12 Mar 2010
First published
08 Apr 2010

Phys. Chem. Chem. Phys., 2010,12, 6404-6412
Article type
Paper

Azobenzene versus 3,3′,5,5′-tetra-tert-butyl-azobenzene (TBA) at Au(111): characterizing the role of spacer groups

E. R. McNellis, C. Bronner, J. Meyer, M. Weinelt, P. Tegeder and K. Reuter, Phys. Chem. Chem. Phys., 2010, 12, 6404
DOI: 10.1039/C001978J

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