A Molecular Turnstile as an E‐Field‐Triggered Single‐Molecule Switch: Concept and Synthesis

Le Pleux, Loic and Kapatsina, Elisabeth and Hildesheim, Julia and Haussinger, Daniel and Mayor, Marcel. (2017) A Molecular Turnstile as an E‐Field‐Triggered Single‐Molecule Switch: Concept and Synthesis. European Journal of Organic Chemistry, 2017 (22). pp. 3165-3178.

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Official URL: https://edoc.unibas.ch/63135/

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A new single-molecule switching concept relying on the E-field-dependent orientation of a push-pull system (via its dipole moment) is presented. As first steps towards realizing the E-field-triggered single-molecule motion, the synthesis of turnstile 1, which is designed to bridge a gap within a carbon nanotube junction, is reported. Turnstile 1 consists of a hexakis(m-phenyleneethynylene) macrocycle decorated with phenanthrene-functionalized oligo(phenyleneethynylene) (OPE) wires at opposite ends, as well as a para-connected push-pull rod as rotator unit. The similarity of the rotor dimension with the surrounding macrocycle guarantees efficient p-stacking between both subunits when an E-field is applied. To introduce a dipole moment into the rotator, the structure is terminally functionalized with a nitrile group on one side and with a dimethylamino group on the opposite end. Synthetic protocols based on Sonogashira-Hagihara couplings were developed to build up the macrocycle scaffold. The highly functionalized open precursor A is the key building block of the sequence as it allows a twofold intramolecular palladium-catalyzed cyclization reaction to be performed to obtain the target turnstile in a very good yield of 68 %. The target structure was fully characterized by NMR spectroscopy and mass spectrometry. Furthermore, H-1-H-1 NOESY NMR experiments pointed to a pseudo-rotation of the push-pull rod within the turnstile structure on the time scale of the NMR experiment.
Faculties and Departments:05 Faculty of Science > Departement Chemie
05 Faculty of Science > Departement Chemie > Chemie > Molecular Devices and Materials (Mayor)
05 Faculty of Science > Departement Chemie > Chemie > Nuclear Magnetic Resonance (Häussinger)
UniBasel Contributors:Mayor, Marcel and Le Pleux, Loïc and Kapatsina, Elissavet and Hildesheim, Julia and Häussinger, Daniel
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:16 Apr 2018 06:56
Deposited On:16 Apr 2018 06:56

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