Self-assembled monolayers from biphenyldithiol derivatives: optimization of the deprotection procedure and effect of the molecular conformation

The Journal of Physical Chemistry. B
Andrey ShaporenkoMichael Zharnikov

Abstract

A series of biphenyl-derived dithiol (BDDT) compounds with terminal acetyl-protected sulfur groups and different structural arrangements of both phenyl rings have been synthesized and fully characterized. The different arrangements were achieved by introducing hydrocarbon substituents in the 2 and 2' positions of the biphenyl backbone. The presented model compounds enable the investigation of the correlation between the intramolecular conformation and other physical properties of interest, like, e.g., molecular assembly or electronic transport properties. Here, the ability of these model compounds to form self-assembled monolayers (SAMs) on Au(111) and Ag(111) is investigated in details. The deprotection of the target molecules was performed in situ using either NH4OH or triethylamine (TEA) deprotection agent. The fabricated films were characterized by synchrotron-based high-resolution photoelectron spectroscopy and near-edge absorption fine structure spectroscopy. Whereas the deprotection by NH4OH was found to result in the formation of multilayer films, the deprotection by TEA allowed the preparation of densely packed BDDT SAMs with a noticeably higher orientational order and smaller molecular inclination on Ag than on Au. In...Continue Reading

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Citations

Oct 2, 2012·The Journal of Chemical Physics·Enrico Benassi, Stefano Corni
Aug 28, 2012·The Journal of Chemical Physics·Robert StadlerVictor Geskin
Apr 7, 2007·Angewandte Chemie·Mihaela G BadinChristof Wöll
Oct 11, 2008·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Emanuel LörtscherHeike Riel
Apr 24, 2010·Advanced Materials·Georg HeimelEgbert Zojer
Aug 10, 2010·Physical Chemistry Chemical Physics : PCCP·Frederick ChesneauMichael Zharnikov
Jan 20, 2012·Beilstein Journal of Nanotechnology·Einat TiroshSidney R Cohen
May 28, 2008·Langmuir : the ACS Journal of Surfaces and Colloids·Cai ShenMichael Zharnikov
Apr 2, 2008·Journal of the American Chemical Society·Núria CrivillersConcepció Rovira
Dec 23, 2009·Nano Letters·Artem MishchenkoThomas Wandlowski
Mar 10, 2011·Journal of the American Chemical Society·Hennie ValkenierJan C Hummelen
Dec 12, 2019·ACS Applied Materials & Interfaces·Frank S BenneckendorfKlaus Müllen
Dec 1, 2006·The Journal of Physical Chemistry. B·Andrey ShaporenkoMichael Zharnikov
Oct 5, 2021·Langmuir : the ACS Journal of Surfaces and Colloids·Lixian TianWenping Hu

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