Quinone-Based, Redox-Active Resorcin[4]arene Cavitands

Authors

  • Igor Pochorovski,

    1. Laboratorium für Organische Chemie, ETH Zürich, Hönggerberg, HCI, 8093 Zürich (Switzerland)
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  • Prof. Dr. Corinne Boudon,

    1. Laboratoire d'Electrochimie et de Chimie Physique du Corps Solide, Institut de Chimie-UMR 7177, C.N.R.S., Université de Strasbourg, 4, rue Blaise Pascal, 67081 Strasbourg Cedex (France)
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  • Dr. Jean-Paul Gisselbrecht,

    1. Laboratoire d'Electrochimie et de Chimie Physique du Corps Solide, Institut de Chimie-UMR 7177, C.N.R.S., Université de Strasbourg, 4, rue Blaise Pascal, 67081 Strasbourg Cedex (France)
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  • Dr. Marc-Olivier Ebert,

    1. Laboratorium für Organische Chemie, ETH Zürich, Hönggerberg, HCI, 8093 Zürich (Switzerland)
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  • Dr. W. Bernd Schweizer,

    1. Laboratorium für Organische Chemie, ETH Zürich, Hönggerberg, HCI, 8093 Zürich (Switzerland)
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  • Prof. Dr. François Diederich

    Corresponding author
    1. Laboratorium für Organische Chemie, ETH Zürich, Hönggerberg, HCI, 8093 Zürich (Switzerland)
    • Laboratorium für Organische Chemie, ETH Zürich, Hönggerberg, HCI, 8093 Zürich (Switzerland)
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  • This work was supported by a grant from the Swiss National Science Foundation (SNF). I.P. acknowledges the receipt of a fellowship from the Fonds der Chemischen Industrie. We thank Prof. Dr. Bernhard Jaun for helpful discussions and Dr. Melanie Chiu for reviewing the manuscript.

Abstract

original image

Catch it if you can! Redox-active resorcin[4]arene cavitands with quinone walls can be reversibly reduced to the hydroquinone form, influencing their host–guest complexation strength. Specifically, a top-covered triptycenequinone cavitand forms kinetically stable complexes with cycloalkanes; this complexation is weaker in the reduced hydroquinone form.

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