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Molecules 2014, 19(9), 15298-15313; doi:10.3390/molecules190915298

Electrochemistry of the Self-Assembled Monolayers of Dyads Consisting of Tripod-Shaped Trithiol and Bithiophene on Gold

1
Department of Chemistry for Materials, Graduate School of Engineering, Mie University, Tsu, Mie 514-8507, Japan
2
Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011, Japan
*
Author to whom correspondence should be addressed.
Received: 11 August 2014 / Revised: 2 September 2014 / Accepted: 17 September 2014 / Published: 24 September 2014
(This article belongs to the Section Organic Synthesis)
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Abstract

Self-assembled monolayers (SAMs) of tripod-shaped trithiols, consisting of an adamantane core with three CH2SH legs and a bithiophene group, were prepared on a Au(111) surface. Adsorption in a tripod-like fashion was supported by polarization modulation-infrared reflection absorption spectroscopy (PM-IRRAS) of the SAMs, which indicated the absence of free SH groups. Cyclic voltammetry showed an irreversible cathodic wave due to reductive desorption. The SAM also showed an anodic wave due to the single-electron oxidation of the bithiophene moiety without concomitant desorption of the molecules. Although oxidation was irreversible in the absence of a protecting group, it became reversible with the introduction of a terminal phenyl group. The charge of the oxidation was one-third that of the reductive desorption, confirming a three-point adsorption. The surface coverage was ca. 50% of that expected for the anti bithiophene conformation, which suggested that an increase in the surface area per molecule had been caused by the presence of an energetically high-lying syn conformer. In accordance with this, the line shape of the oxidation wave suggested an electrostatic repulsive interaction between neighboring molecules. View Full-Text
Keywords: self-assembled monolayer; molecular tripod; bithiophene; adamantane; cyclic voltammetry self-assembled monolayer; molecular tripod; bithiophene; adamantane; cyclic voltammetry
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MDPI and ACS Style

Kitagawa, T.; Matsubara, H.; Okazaki, T.; Komatsu, K. Electrochemistry of the Self-Assembled Monolayers of Dyads Consisting of Tripod-Shaped Trithiol and Bithiophene on Gold. Molecules 2014, 19, 15298-15313.

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