Redox-active catechol-functionalized molecular rods: Suitable protection groups and single-molecule transport investigations

Nicolas Weibel, Alfred Błaszczyk, Carsten Von Hänisch, Marcel Mayor, Ilya Pobelov, Thomas Wandlowski, Fang Chen, Nongjian Tao

Research output: Contribution to journalArticle

21 Scopus citations

Abstract

The synthesis of molecular rod 1 comprising a central redox-active unit and two terminal acetyl-protected sulfur groups is reported. Various protecting groups for the catechol moiety were investigated and protected precursors 14-18 were synthesized. In particular, ethyl orthoformate 17 can be easily and selectively deprotected in mild acidic conditions ruling out the need for a strong Lewis acid like boron tribromide. The redox activity of 1 was confirmed by cyclic voltammetric investigations. Gold-molecule-gold junctions were formed with the dimethyl-protected rod 18. Single-molecule transport investigations using this molecular rod revealed a set of three single-junction conductance values varying over two orders of magnitude.

Original languageEnglish (US)
Pages (from-to)136-149
Number of pages14
JournalEuropean Journal of Organic Chemistry
Issue number1
DOIs
StatePublished - Jan 15 2008

Keywords

  • Catechol
  • Electrochemistry
  • Molecular electronics
  • Molecular rods
  • Protecting groups
  • Single-molecule conductance

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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