Redox-Active Catechol-Functionalized Molecular Rods: Suitable Protection Groups and Single-Molecule Transport Investigations
✍ Scribed by Nicolas Weibel; Alfred Błaszczyk; Carsten von Hänisch; Marcel Mayor; Ilya Pobelov; Thomas Wandlowski; Fang Chen; Nongjian Tao
- Book ID
- 102827795
- Publisher
- John Wiley and Sons
- Year
- 2008
- Tongue
- English
- Weight
- 698 KB
- Volume
- 2008
- Category
- Article
- ISSN
- 1434-193X
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✦ Synopsis
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.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)