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Paramagnetic Molecular Grippers: The Elements of Six-State Redox Switches

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Download Hi-Res ImageDownload to MS-PowerPointCite This:J. Phys. Chem. Lett. 2016, 7, 13, 2470-2477
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    Paramagnetic Molecular Grippers: The Elements of Six-State Redox Switches
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    † Laboratory of Organic Chemistry, ETH Zurich, Vladimir-Prelog-Weg 3, 8093 Zurich, Switzerland
    ‡ Max Planck Institute for Chemical Energy Conversion, Stiftstrasse 34-36, 45470 Mülheim an der Ruhr, Germany
    § Institute of Physical Chemistry and Chemical Physics, Slovak University of Technology in Bratislava, Faculty of Chemical and Food Technology, Radlinského 9, 81237 Bratislava, Slovak Republic
    ∥ Department of Chemistry, University of Basel, St. Johanns-Ring 19, 4056 Basel, Switzerland
    ⊥ Institute of Physical and Theoretical Chemistry, NAWI Graz, Graz University of Technology, Stremayrgasse 9/Z2, 8010 Graz, Austria
    # Université de Strasbourg, Laboratoire d’Électrochimie et Chimie Physique du Corps Solide, Institut de Chimie de Strasbourg, 4 rue Blaise Pascal, CS 90032, 67081 Strasbourg, France
    *E-mail: [email protected]
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    The Journal of Physical Chemistry Letters

    Cite this: J. Phys. Chem. Lett. 2016, 7, 13, 2470–2477
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.jpclett.6b01094
    Published June 14, 2016
    Copyright © 2016 American Chemical Society
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    Abstract

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    The development of semiquinone-based resorcin[4]arene cavitands expands the toolbox of switchable molecular grippers by introducing the first paramagnetic representatives. The semiquinone (SQ) states were generated electrochemically, chemically, and photochemically. We analyzed their electronic, conformational, and binding properties by cyclic voltammetry, ultraviolet/visible (UV/vis) spectroelectrochemistry, electron paramagnetic resonance (EPR) and transient absorption spectroscopy, in conjunction with density functional theory (DFT) calculations. The utility of UV/vis spectroelectrochemistry and EPR spectroscopy in evaluating the conformational features of resorcin[4]arene cavitands is demonstrated. Guest binding properties were found to be enhanced in the SQ state as compared to the quinone (Q) or the hydroquinone (HQ) states of the cavitands. Thus, these paramagnetic SQ intermediates open the way to six-state redox switches provided by two conformations (open and closed) in three redox states (Q, SQ, and HQ) possessing distinct binding ability. The switchable magnetic properties of these molecular grippers and their responsiveness to electrical stimuli has the potential for development of efficient molecular devices.

    Copyright © 2016 American Chemical Society

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    Supporting Information

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.jpclett.6b01094.

    • Synthesis, NMR spectroscopy, crystal structure data, electrochemistry, EPR spectroscopy, UV/vis spectroscopy and UV/vis/NIR spectroelectrochemistry, time-resolved luminescence and transient absorption spectroscopy, binding studies, and DFT calculations (PDF)

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    Cited By

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    This article is cited by 12 publications.

    1. Cornelius Gropp, Brendan L. Quigley, and François Diederich . Molecular Recognition with Resorcin[4]arene Cavitands: Switching, Halogen-Bonded Capsules, and Enantioselective Complexation. Journal of the American Chemical Society 2018, 140 (8) , 2705-2717. https://doi.org/10.1021/jacs.7b12894
    2. Vladimir A. Azov, Francois J. De Beer. Redox‐Responsive Macrocyclic Hosts Based on Calix[4]arene and Calix[4]resorcinarene Scaffolds. Israel Journal of Chemistry 2024, 64 (6-7) https://doi.org/10.1002/ijch.202300075
    3. Parnian Ferdowsi, Ullrich Steiner, Jovana V Milić. Host-guest complexation in hybrid perovskite optoelectronics. Journal of Physics: Materials 2021, 4 (4) , 042011. https://doi.org/10.1088/2515-7639/ac299f
    4. Víctor García‐López, Michal Zalibera, Nils Trapp, Martin Kuss‐Petermann, Oliver S. Wenger, François Diederich. Stimuli‐Responsive Resorcin[4]arene Cavitands: Toward Visible‐Light‐Activated Molecular Grippers. Chemistry – A European Journal 2020, 26 (50) , 11451-11461. https://doi.org/10.1002/chem.202001788
    5. Anna Szafraniec, Waldemar Iwanek. Intramolecular Hydrogen Bond Driven Conformational Selectivity of Coumarin Derivatives of Resorcin[4]arene. International Journal of Molecular Sciences 2020, 21 (17) , 6160. https://doi.org/10.3390/ijms21176160
    6. Jovana V. Milić, Thomas Schneeberger, Michal Zalibera, François Diederich, Corinne Boudon, Laurent Ruhlmann. Spectro-electrochemical toolbox for monitoring and controlling quinone-mediated redox-driven molecular gripping. Electrochimica Acta 2019, 313 , 544-560. https://doi.org/10.1016/j.electacta.2019.04.049
    7. Jovana V. Milić, François Diederich. The Quest for Molecular Grippers: Photo‐Electric Control of Molecular Gripping Machinery. Chemistry – A European Journal 2019, 25 (36) , 8440-8452. https://doi.org/10.1002/chem.201900852
    8. David F. Hahn, Jovana V. Milić, Philippe H. Hünenberger. Vase ‐ Kite Equilibrium of Resorcin[4]arene Cavitands Investigated Using Molecular Dynamics Simulations with Ball‐and‐Stick Local Elevation Umbrella Sampling. Helvetica Chimica Acta 2019, 102 (5) https://doi.org/10.1002/hlca.201900060
    9. Marlon D.L. Tonin, Simon J. Garden, Mukesh M. Jotani, James L. Wardell, Edward R.T. Tiekink. On the influence of small chemical changes upon the supramolecular association in substituted 2-(phenoxy)-1,4-naphthoquinones. Zeitschrift für Kristallographie - Crystalline Materials 2019, 234 (3) , 183-200. https://doi.org/10.1515/zkri-2018-2129
    10. Jovana V. Milić, Thomas Schneeberger, Michal Zalibera, Karolina Z. Milowska, Quy K. Ong, Nils Trapp, Laurent Ruhlmann, Corinne Boudon, Carlo Thilgen, François Diederich. Thioether‐Functionalized Quinone‐Based Resorcin[4]arene Cavitands: Electroswitchable Molecular Actuators. Helvetica Chimica Acta 2019, 102 (2) https://doi.org/10.1002/hlca.201800225
    11. Víctor García-López, Jovana V. Milić, Michal Zalibera, Dmytro Neshchadin, Martin Kuss-Petermann, Laurent Ruhlmann, Julia Nomrowski, Nils Trapp, Corinne Boudon, Georg Gescheidt, Oliver S. Wenger, François Diederich. Light-actuated resorcin[4]arene cavitands. Tetrahedron 2018, 74 (39) , 5615-5626. https://doi.org/10.1016/j.tet.2018.08.002
    12. Jovana Milić, Michal Zalibera, Darius Talaat, Julia Nomrowski, Nils Trapp, Laurent Ruhlmann, Corinne Boudon, Oliver S. Wenger, Anton Savitsky, Wolfgang Lubitz, François Diederich. Photoredox‐Switchable Resorcin[4]arene Cavitands: Radical Control of Molecular Gripping Machinery via Hydrogen Bonding. Chemistry – A European Journal 2018, 24 (6) , 1431-1440. https://doi.org/10.1002/chem.201704788
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    The Journal of Physical Chemistry Letters

    Cite this: J. Phys. Chem. Lett. 2016, 7, 13, 2470–2477
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.jpclett.6b01094
    Published June 14, 2016
    Copyright © 2016 American Chemical Society
    Request reuse permissions

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