Zwitterionic dithiocarboxylates derived from N-heterocyclic carbenes: coordination to gold surfaces

Ulrich Siemeling; Henry Memczak; Clemens Bruhn; Florian Vogel; Frank Träger; Joe E. Baio; Tobias Weidner

doi:10.1039/C2DT11976E

Zwitterionic dithiocarboxylates derived from N-heterocyclic carbenes: coordination to gold surfaces†

Ulrich Siemeling,*^ac Henry Memczak,‡^ac Clemens Bruhn,^a Florian Vogel,^bc Frank Träger,^bc Joe E. Baio^d and Tobias Weidner^d

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* Corresponding authors

^a Institute of Chemistry, University of Kassel, Heinrich-Plett-Str. 40, Kassel, Germany
E-mail: siemeling@uni-kassel.de

^b Institute of Physics, University of Kassel, Heinrich-Plett-Str. 40, Kassel, Germany

^c Center for Interdisciplinary Nanostructure Science and Technology, University of Kassel, Heinrich-Plett-Str. 40, Kassel, Germany

^d National ESCA and Surface Analysis Center for Biomedical Problems (NESAC/BIO), Departments of Bioengineering and Chemical Engineering, University of Washington, Seattle, Washington, USA

Abstract

The zwitterionic dithiocarboxylates 1⁺–CS₂⁻–4⁺–CS₂⁻ were prepared by reacting the corresponding N-heterocyclic carbenes 1,3-bis(2,6-diisoproylphenyl)imidazol-2-ylidene (1), 1,3-diisopropylimidazol-2-ylidene (2), 1,3-dibenzylimidazol-2-ylidene (3) and 1,3-diethylbenzimidazol-2-ylidene (4) with CS₂. In the latter two cases, the corresponding N-heterocylic carbene was generated in situ. Compounds 2⁺–CS₂⁻–4⁺–CS₂⁻ were structurally characterised by single-crystal X-ray diffraction studies. The chemisorption of these zwitterionic dithiocarboxylates on solid gold substrates was investigated in situ and in real time by optical second harmonic generation (SHG). The resulting thin films were exemplarily characterised by near-edge X-ray absorption fine structure (NEXAFS) spectroscopy and X-ray photoelectron spectroscopy (XPS) in the case of 1⁺–CS₂⁻ and 2⁺–CS₂⁻, revealing the formation of almost contamination-free self-assembled monolayers, which exhibit a remarkable degree of orientational order.

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DOI: https://doi.org/10.1039/C2DT11976E
Article type: Paper
Submitted: 19 Oct 2011
Accepted: 05 Dec 2011
First published: 25 Jan 2012

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Dalton Trans., 2012,41, 2986-2994

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Zwitterionic dithiocarboxylates derived from N-heterocyclic carbenes: coordination to gold surfaces

U. Siemeling, H. Memczak, C. Bruhn, F. Vogel, F. Träger, J. E. Baio and T. Weidner, Dalton Trans., 2012, 41, 2986 DOI: 10.1039/C2DT11976E

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Dalton Transactions

Zwitterionic dithiocarboxylates derived from N-heterocyclic carbenes: coordination to gold surfaces†

Abstract

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Zwitterionic dithiocarboxylates derived from N-heterocyclic carbenes: coordination to gold surfaces

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