Catechol-based macrocyclic rods : en route to redox-active molecular switches

Weibel, Nicolas and Mishchenko, Artem and Wandlowski, Thomas and Neuburger, Markus and Leroux, Yann and Mayor, Marcel. (2009) Catechol-based macrocyclic rods : en route to redox-active molecular switches. European Journal of Organic Chemistry, 2009 (35). pp. 6140-6150.

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Official URL: http://edoc.unibas.ch/dok/A5259890

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The design and synthesis of the macrocyclic turnstile 1 comprising a terminally sulfur-functionalized molecular rod and a redox-active catechol subunit is described. The shape-persistent macrocyclic scaffold consists of alternating arylene and ethynylene units. A freely rotating 2,6-diethynyl-catechol subunit is clamped between both terminal arylene subunits as molecular turnstile. While the electrochemical switching between the catechol and the quinone form of this catechol subunit is displayed by cyclic voltammetry, conformational rearrangements by favoring and disfavoring the formation of intramolecular hydrogen bonds are the subject of current investigations. Terminal acetyl-protected sulfur anchor groups enabled the immobilization of the macrocycle between an Au tip and an Au substrate of a STM set-up. Preliminary single-molecule transport investigations of the turnstile 1 display comparable values as for the parent molecular rod. An electrochemically-controlled single-molecule transport experiment to investigate redox-state-dependent transport properties is currently under way.
Faculties and Departments:05 Faculty of Science > Departement Chemie > Chemie > Molecular Devices and Materials (Mayor)
UniBasel Contributors:Mayor, Marcel
Item Type:Article, refereed
Article Subtype:Research Article
Note:Publication type according to Uni Basel Research Database: Journal article
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Last Modified:05 Apr 2017 14:16
Deposited On:22 Mar 2012 14:06

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