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Issue 40, 2019
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A dithiocarbamate anchoring group as a flexible platform for interface engineering

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Abstract

The molecular organization and electronic properties of dithiocarbamate (DTC) anchored self-assembled monolayers (SAMs) linked to Au(111) substrates are studied by a combination of X-ray photoelectron spectroscopy (XPS), near-edge X-ray absorption fine structure (NEXAFS) spectroscopy, and state-of-the-art density functional theory calculations. For that, several piperidine/piperazine precursors with different architecture and substitution patterns are selected. The presented data show that the DTC anchor provides a useful building block for monomolecular self-assembly on coinage metals with both sulfur atoms bonded to the substrate in a way similar to what is usually observed for the more commonly applied thiolate docking group. The combination of the DTC group with the quite flexible piperidine/piperazine cyclic linkers results in a dense molecular packing with an upright orientation of the terminal moieties. The latter comprise phenyl rings bearing various substituents, which enables tuning the interfacial dipole over a wide range. Simulations on two prototypical DTC-docked SAMs help to better understand the experimental observations and provide insight into the local origin of the SAM-induced shifts in the electrostatic energy. In particular, a comparison of measured and simulated XP spectra reveals the significant contribution of the DTC group to the interfacial dipole.

Graphical abstract: A dithiocarbamate anchoring group as a flexible platform for interface engineering

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Publication details

The article was received on 11 Jun 2019, accepted on 24 Sep 2019 and first published on 04 Oct 2019


Article type: Paper
DOI: 10.1039/C9CP03306H
Phys. Chem. Chem. Phys., 2019,21, 22511-22525
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    A dithiocarbamate anchoring group as a flexible platform for interface engineering

    E. Sauter, G. Nascimbeni, D. Trefz, S. Ludwigs, E. Zojer, F. von Wrochem and M. Zharnikov, Phys. Chem. Chem. Phys., 2019, 21, 22511
    DOI: 10.1039/C9CP03306H

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