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Efficient nucleophilic substitution in self-assembled monolayer of dithiol on gold

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Chemistry of Heterocyclic Compounds Aims and scope

Many self-assembled monolayers of dithiols on gold feature terminal SH groups, the nucleophilic nature of which provides opportunities for covalent binding of electrophiles through sulfide linkages. This work describes an efficient coupling of dithiol derivative of 4,4'-dihydroxybiphenyl immobilized on Au surface with a mesylate ester present in the solution. The procedure did not require a glove box or any specialized equipment and provided a high surface concentration of the redox active product. The modified Au-SAM electrode was investigated electroanalytically.

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This work was supported by the National Science Center of Poland (OPUS No. 2014/13/B/ ST5/03727). K.M.T. is supported by the Foundation for Polish Science.

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Authors and Affiliations

  1. Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-231, Warsaw, Poland

    Mateusz Woźny & Karolina M. Tomczyk

  2. Department of Microbioanalytics, Faculty of Chemistry, Warsaw University of Technology, Noakowskiego 3, 00-664, Warsaw, Poland

    Urszula E. Wawrzyniak

Authors
  1. Mateusz Woźny
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  2. Karolina M. Tomczyk
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  3. Urszula E. Wawrzyniak
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Correspondence to Mateusz Woźny.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2017, 53(1), 97–100

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Woźny, M., Tomczyk, K.M. & Wawrzyniak, U.E. Efficient nucleophilic substitution in self-assembled monolayer of dithiol on gold. Chem Heterocycl Comp 53, 97–100 (2017). https://doi.org/10.1007/s10593-017-2027-7

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  • DOI: https://doi.org/10.1007/s10593-017-2027-7

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