Gold-Induced Desulfurization in a Bis(ferrocenyl) Alkane Dithiol

Evangelina Pensa, Rafał Karpowicz, Artur Jabłoński, Damian Trzybiński, Krzysztof Woźniak, Davor Šakić, Valerije Vrček, Nicholas J. Long, Tim Albrecht, Konrad Kowalski

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Thiol-modified ferrocenes on gold have been archetypical model systems for many fundamental charge transfer and other studies, since both thiol-gold and ferrocene redox chemistry are considered to be well-understood. Thus unexpectedly, we found that for a representative of a new class of flexibly linked bis-ferrocenyl compounds, namely, 1-10-bis(1-ferrocenyl)decane dithiol, surface immobilization on gold failed. Instead, in the presence of gold, molecular decomposition took place, resulting in sulfur-based adlayers and well-defined molecular elimination products, for which we provide spectroscopic evidence. Careful control experiments and comparison with related ferrocene compounds provide insight into the mechanism of the observed elimination reactions, as a combined effect of the molecular structure and the nature of the gold/sulfur bond. These findings, thus, have a broader impact on the design of molecular adlayers, for example, in the context of surface functionalization in sensing or the synthesis of gold nanoparticles.
Original languageEnglish
Pages (from-to)2227-2232
Number of pages6
Issue number9
Early online date17 Apr 2019
Publication statusPublished - 13 May 2019

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry


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