Synthesis of Organic Thiosulfates Tailored for the Electrochemical Deposition of ‘Self-Assembled Monolayers’ at Gold Surfaces

Eliso Gogritchiani; Sandra Niebler; Nicole Egner; Michael Wörner; André M. Braun; Tanya Young; Prachi Gupta; Aibin Shi; Stefan H. Bossmann

doi:10.1055/s-2005-916026

PAPER

Synthesis of Organic Thiosulfates Tailored for the Electrochemical Deposition of ‘Self-Assembled Monolayers’ at Gold Surfaces

Eliso Gogritchiani*^a, Sandra Niebler^a, Nicole Egner^a, Michael Wörner^a, André M. Braun*^a, Tanya Young^b, Prachi Gupta^b, Aibin Shi^b, Stefan H. Bossmann*^a,b
^a University of Karlsruhe, Department of Chemical & Process Engineering, 76128 Karlsruhe, Germany
e-Mail: eliso.g@ciw.uni-karlsruhe.de; e-Mail: andre.braun@ciw.uni-karlsruhe.de;
^b Kansas State University, Department of Chemistry, 111 Willard Hall, Manhattan, Kansas 66506-3701, USA
Fax: +1(785)5326666; e-Mail: sbossman@ksu.edu;

Abstract

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Abstract

The synthesis of organic thiosulfates, up to 10 nm in length, which were tailored for generating artificial monomembranes on gold surfaces by electrochemically initiated deposition, was accomplished. (E)-3-(4-Hydroxyphenyl)acrylic acid (4-hydroxy cinnamic acid) was employed as aromatic head group and (C₁₀H₂₀-O-)_n (n = 1, 3, 5, 7) building blocks were attached. The synthetic procedure comprises a series of nucleophilic substitutions under carefully defined conditions. Extended purification is crucial for eliminating non-reacted starting materials.

Key words

self-assembled monolayer (SAM) - organic thiosulfates (Bunte salts) - oligoether - long-chain surfactants - nucleophilic substitution

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