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Synthesis 2004(14): 2283-2288  
DOI: 10.1055/s-2004-831163
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Novel Alkyl- and Aryl Sulfides and Thiols as Precursors for Self-Assembled Monolayers on Gold

Mohamed Touaibia, Marc-André Desjardins, Alexandre Provençal, Daniel Audet, Christelle Médard, Mario Morin, Livain Breau*
Département de Chimie and Laboratoire de Synthèse Organique Appliquée, Département de Chimie, Université du Québec à Montréal, Case Postale 8888, Succursale Centre-Ville, Montréal, Québec, H3C 3P8, Canada
e-Mail: breau.livain@uqam.ca;
Further Information

Publication History

Received 13 April 2004
Publication Date:
23 August 2004 (online)

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Abstract

A series of 4-alkyl-1-bromosulfanylbenzenes having S-methyl 2, S-t-butyl 3, S-trityl 4, S-benzyl 5, and S-silylethoxymethyl 6 substituents were prepared and evaluated for their ability to form a monolayer consisting of an S-aryl adsorbate on Au (111) surface. The monolayer was formed via the selective hydrolytic removal of an alkyl group protecting the sulfur functionality upon adsorbtion onto the gold surface. Thiols having variable carbon chain length and a peripheral thiophene moiety 9, 10, 17, 18 and 23-26 were also prepared.

Key words

4-alkyl-1-bromosulfanyl benzenes - 4-thienylthiophenols - thienylalkanethiols - self-assembled monolayers on gold

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Touaibia, M.; Benny, F.; Pilon, C.; Courtel, F.; Breau, L.; Morin, M.; J. Phys. Chem. B; submitted, 2004.