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Electrochemical dimerization of 2-(2’-thienyl)pyridine adsorbed on Au(111) observed by in situ fluorescence

TitleElectrochemical dimerization of 2-(2’-thienyl)pyridine adsorbed on Au(111) observed by in situ fluorescence
Publication TypeJournal Article
Year of Publication2004
AuthorsChung, E, Shepherd, JL, Bizzotto, D, Wolf, MO
JournalLangmuir
Volume20
Pagination8270-8278
Date PublishedSep
Type of ArticleArticle
ISBN Number0743-7463
KeywordsADSORPTION, CHAIN-LENGTH, CONDUCTING COPOLYMERS, DONATING, electrode, GOLD, PYRIDINE, SCANNING-TUNNELING-MICROSCOPY, SELF-ASSEMBLED MONOLAYERS, SOLUTION INTERFACE, THIOPHENE UNITS
Abstract

The study of heterodentate molecules adsorbed on metal electrodes provides an opportunity to expand the functionality of modified surfaces while offering insights into the surface and intramolecular electronic interactions of organic adsorbates. The adsorption of 2-(2’-thienyl)pyridine, a molecule containing both pyridine and thiophene moieties, on a Au(111) electrode is reported. Adsorption was characterized by electrochemistry in neutral and basic aqueous electrolyte and was compared to that of pyridine. The aqueous electrochemistry of thiophene on Au(111) was also characterized for comparison purposes. At negative potentials, in the presence of 2-(2’-thienyl)pyridine, a diffuse, pi-bonded monolayer was formed, and a phase transition to a close-packed N- and/or S-bonded configuration was observed near -0.4 V in a 1 mM solution of adsorbate, similar to that seen in pyridine on Au(111). The thiophene-like oxidative dimerization of the molecule was confirmed at positive potentials using in situ fluorescence microscopy by comparison with the spectrum of the chemically synthesized dimer.

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