Strapped-Porphyrin-Based Molecular Turnstiles

Authors

  • Dr. Thomas Lang,

    1. Department of Chemistry, Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford, OX1 3TA (UK)
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  • Dr. Ernest Graf,

    Corresponding author
    1. Laboratoire de Chimie de Coordination Organique, UMR UdS-CNRS 7140, Institut Le Bel, Université de Strasbourg, 4 rue Blaise Pascal, CS 90032, 67081 Strasbourg cedex (France), Fax: (+33) 368-85-13-25
    • Laboratoire de Chimie de Coordination Organique, UMR UdS-CNRS 7140, Institut Le Bel, Université de Strasbourg, 4 rue Blaise Pascal, CS 90032, 67081 Strasbourg cedex (France), Fax: (+33) 368-85-13-25
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  • Nathalie Kyritsakas,

    1. Laboratoire de Chimie de Coordination Organique, UMR UdS-CNRS 7140, Institut Le Bel, Université de Strasbourg, 4 rue Blaise Pascal, CS 90032, 67081 Strasbourg cedex (France), Fax: (+33) 368-85-13-25
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  • Prof. Dr. Mir Wais Hosseini

    Corresponding author
    1. Laboratoire de Chimie de Coordination Organique, UMR UdS-CNRS 7140, Institut Le Bel, Université de Strasbourg, 4 rue Blaise Pascal, CS 90032, 67081 Strasbourg cedex (France), Fax: (+33) 368-85-13-25
    • Laboratoire de Chimie de Coordination Organique, UMR UdS-CNRS 7140, Institut Le Bel, Université de Strasbourg, 4 rue Blaise Pascal, CS 90032, 67081 Strasbourg cedex (France), Fax: (+33) 368-85-13-25
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Abstract

The synthesis of a series of molecular turnstiles that contained both H-bond-donor and -acceptor sites was achieved. Their structures were based on tetra-aryl X2SnIV porphyrins (X=Cl or OH) as H-bond-acceptor sites that were equipped with a rotor that contained a pyridyldiamide moiety as a H-bond donor. In the solution phase, 1D and 2D NMR spectroscopic analysis showed that switching between the closed state, which resulted from the formation of intramolecular H-bonds, and the open state of the turnstile was achieved by using external H-bond-acceptor molecules, such as DMSO. The solid-state structure of the closed state of the turnstile was established by single-crystal X-ray diffraction.

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