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

20 Citations (Scopus)

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 - 2008

Fingerprint

Gold
Lewis Acids
Molecules
Boron
Sulfur
catechol
Oxidation-Reduction

Keywords

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

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Redox-active catechol-functionalized molecular rods : Suitable protection groups and single-molecule transport investigations. / Weibel, Nicolas; Błaszczyk, Alfred; Von Hänisch, Carsten; Mayor, Marcel; Pobelov, Ilya; Wandlowski, Thomas; Chen, Fang; Tao, Nongjian.

In: European Journal of Organic Chemistry, No. 1, 2008, p. 136-149.

Research output: Contribution to journalArticle

Weibel, Nicolas ; Błaszczyk, Alfred ; Von Hänisch, Carsten ; Mayor, Marcel ; Pobelov, Ilya ; Wandlowski, Thomas ; Chen, Fang ; Tao, Nongjian. / Redox-active catechol-functionalized molecular rods : Suitable protection groups and single-molecule transport investigations. In: European Journal of Organic Chemistry. 2008 ; No. 1. pp. 136-149.
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