Electrochemical study of self-assembled monolayers of a β-cyclodextrin methyl sulfide covalently linked to anthraquinone

Keith J. Stine, Donna M. Andrauskas, Abdul R. Khan, Peter Forgo, Valerian T. D'Souza

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Self-assembled monolayers of a β-cyclodextrin with methyl sulfides on the primary sites of the molecule and mono-functionalized with anthraquinone on a secondary site have been formed on gold electrodes. The surface coverages obtained by electrochemistry are consistent with values reported previously or calculated for similar non-electroactive β-CD derivatives. The electron transfer rate constants vary markedly with pH, increasing rapidly between pH 7 and 9 to values of approximately 700-900 s-1. These values are faster than reported previously for thiol derivatives of anthraquinone dispersed in an alkylthiol SAM matrix. Near pH 6, slow electron transfer is observed with a splitting into individual one-electron steps. Lowering the pH further results in very sluggish kinetics and indistinguishable peaks. Inclusion of naphthalene into the β-CD cavity appears to affect the anodic rate constant, and a small potential shift occurs. The efficient electron transfer of the anthraquinone spaced from the gold surface by a β-CD unit suggests promise for use of such molecules as `immobilized artificial enzymes'.

Original languageEnglish
Pages (from-to)209-218
Number of pages10
JournalJournal of Electroanalytical Chemistry
Issue number2
Publication statusPublished - Apr 29 1999


ASJC Scopus subject areas

  • Analytical Chemistry
  • Chemical Engineering(all)
  • Electrochemistry

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