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Add a third hook: S-acetyl protected oligophenylene pyridine dithiols as advanced precursors for self-assembled monolayers

Sander, Fabian and Hermes, Jens Peter and Mayor, Marcel and Hamoudi, Hicham and Zharnikov, Michael. (2013) Add a third hook: S-acetyl protected oligophenylene pyridine dithiols as advanced precursors for self-assembled monolayers. Physical Chemistry, Chemical Physics, 15 (8). pp. 2836-2846.

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Official URL: http://edoc.unibas.ch/dok/A6223578

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Abstract

Self-assembled monolayers (SAMs) of thiols on gold substrates are potentially important systems for future technologies such as molecular electronics and sensing. Especially in molecular electronics a strong interaction and coupling between the “device” molecules and substrate is crucial. In this context, we present here two series of novel SAM precursors, viz. bidentate oligophenylenes with either 1,3-phenylenedimethanethiol or pyridine-2,6-diyldimethanethiol anchoring group. Both series are shown to form densely packed monolayers with a low level of contamination and a high orientational order that are additionally promoted by the interaction between the terminal pyridine moiety and the substrate in the second series. At the same time, most of the SAM constituents do not exhibit a strictly bidentate bonding to the substrate – whereas one anchor group has a thiolate-type bonding, the other is weakly coordinated, unbound, or participating in a disulfide bridge with the adjacent molecules. We believe that such a bonding heterogeneity stems from the fundamental problems of molecular self-assembly in the given case.
Faculties and Departments:05 Faculty of Science > Departement Chemie > Chemie > Molecular Devices and Materials (Mayor)
UniBasel Contributors:Mayor, Marcel and Sander, Fabian and Hermes, Jens
Item Type:Article, refereed
Article Subtype:Research Article
Publisher:Royal Society of Chemistry
ISSN:1463-9076
Note:Publication type according to Uni Basel Research Database: Journal article
Identification Number:
Last Modified:05 Dec 2016 12:39
Deposited On:27 Mar 2014 13:12

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