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An Electrochemically Controllable Nanomechanical Molecular System Utilizing Edge-to-Face and Face-to-Face Aromatic Interactions

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National Creative Research Initiative Center for Superfunctional Materials and Center for Integrated Molecular Systems, Department of Chemistry, Pohang University of Science and Technology, San 31, Hyojadong, Namgu, Pohang 790-784, Korea
Cite this: Org. Lett. 2002, 4, 22, 3971–3974
Publication Date (Web):October 9, 2002
https://doi.org/10.1021/ol0268541
Copyright © 2002 American Chemical Society

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    Abstract

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    A new molecular system, 2,11-dithio[4,4]metametaquinocyclophane containing a quinone moiety, was designed and synthesized. As the quinone moiety can readily be converted into an aromatic π-system (hydroquinone) upon reduction, the nanomechanical molecular cyclophane system exhibits a large flapping motion like a molecular flipper from the electrochemical redox process. The conformational changes upon reduction and oxidation are caused by changes of nonbonding interaction forces (devoid of bond formation/breaking) from the edge-to-face to face-to-face aromatic interactions and vice versa, respectively.

     Center for Superfunctional Materials.

     Center for Integrated Molecular Systems.

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    Experimental procedures and characterizations of compound 1, 35, and 7; X-ray structural information on 1; UV spectra of 1 and 3; X-ray crystal structure of 8. This material is available free of charge via the Internet at http://pubs.acs.org.

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