Mixed Monolayers Formed by the Self-Assembly on Gold of Thiol-Functionalized Anthraquinones and 1-Alkanethiols

Litao Zhang, Tianbao Lu, George W. Gokel, Angel E. Kaifer

Research output: Contribution to journalArticle

119 Scopus citations

Abstract

The self-assembly and electrochemical properties of a series of thiol-functionalized anthraquinone derivatives were studied on gold by cyclic voltammetry. The compounds were 1,8-bis(1,7-dithia-4-oxaheptyl)-anthracene-9,10-dione (1), 1,8-bis(4,7-dioxa-1,10-dithiadecyl)anthracene-9,10-dione (2), and 1-(4,7-dioxa-1,10-dithiadecyl)anthracene-9,10-dione (3). Compounds 1-3 formed self-assembled monolayers on gold with surface coverages of 2.7 × 10-10, 2.5 × 10-10, and 2.9 × 10-10 mol/cm2, respectively. All monolayers showed voltammetric responses in 0.1 M KOH that corresponded to the two-electron reduction of the anthraquinone subunit. However, the voltammetric response was not reversible, exhibiting large peak-to-peak potential splittings (60-80 mV at a scan rate of 0.1 V/s) and other distortions. The voltammetric reversibility increased substantially in mixed monolayers prepared by the competitive self-assembly of one of the anthraquinone derivatives and a 1-alkanethiol (C10 to C18). Interestingly, the anthraquinone derivatives competed quite effectively with alkanethiols for adsorption sites on the gold surface. Compound 2 was found to be optimum in this regard because it has two thiol-terminated chains that may serve as anchoring points to the gold surface.

Original languageEnglish (US)
Pages (from-to)786-791
Number of pages6
JournalLangmuir
Volume9
Issue number3
DOIs
StatePublished - Jan 1 1993

ASJC Scopus subject areas

  • Materials Science(all)
  • Condensed Matter Physics
  • Surfaces and Interfaces
  • Spectroscopy
  • Electrochemistry

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