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Monofunctionalized Fluorinated Bambusurils and Their Conjugates for Anion Transport and Extraction

  • Nicola Alessandro De Simone
    Nicola Alessandro De Simone
    Department of Chemistry, Faculty of Science, Masaryk University, Kamenice 5, 625 00 Brno, Czech Republic
    RECETOX, Faculty of Science, Masaryk University, Kamenice 5, 625 00 Brno, Czech Republic
  • Matúš Chvojka
    Matúš Chvojka
    Department of Chemistry, Faculty of Science, Masaryk University, Kamenice 5, 625 00 Brno, Czech Republic
    RECETOX, Faculty of Science, Masaryk University, Kamenice 5, 625 00 Brno, Czech Republic
    Engineering of Molecular NanoSystems, Ecole polytechnique de Bruxelles, Université libre de Bruxelles, Avenue F.D. Roosevelt 50, CP 165/64, Brussels 1050, Belgium
  • Jana Lapešová
    Jana Lapešová
    Department of Chemistry, Faculty of Science, Masaryk University, Kamenice 5, 625 00 Brno, Czech Republic
    RECETOX, Faculty of Science, Masaryk University, Kamenice 5, 625 00 Brno, Czech Republic
  • Luis Martínez-Crespo
    Luis Martínez-Crespo
    Engineering of Molecular NanoSystems, Ecole polytechnique de Bruxelles, Université libre de Bruxelles, Avenue F.D. Roosevelt 50, CP 165/64, Brussels 1050, Belgium
  • Petr Slávik
    Petr Slávik
    Department of Chemistry, Faculty of Science, Masaryk University, Kamenice 5, 625 00 Brno, Czech Republic
    RECETOX, Faculty of Science, Masaryk University, Kamenice 5, 625 00 Brno, Czech Republic
    More by Petr Slávik
  • Jan Sokolov
    Jan Sokolov
    Department of Chemistry, Faculty of Science, Masaryk University, Kamenice 5, 625 00 Brno, Czech Republic
    RECETOX, Faculty of Science, Masaryk University, Kamenice 5, 625 00 Brno, Czech Republic
    More by Jan Sokolov
  • Stephen J. Butler
    Stephen J. Butler
    Department of Chemistry, Loughborough University, Epinal Way, Loughborough LE11 3TU, U.K.
  • Hennie Valkenier*
    Hennie Valkenier
    Engineering of Molecular NanoSystems, Ecole polytechnique de Bruxelles, Université libre de Bruxelles, Avenue F.D. Roosevelt 50, CP 165/64, Brussels 1050, Belgium
    *Email: [email protected]
  • , and 
  • Vladimír Šindelář*
    Vladimír Šindelář
    Department of Chemistry, Faculty of Science, Masaryk University, Kamenice 5, 625 00 Brno, Czech Republic
    RECETOX, Faculty of Science, Masaryk University, Kamenice 5, 625 00 Brno, Czech Republic
    *Email: [email protected]
Cite this: J. Org. Chem. 2022, 87, 15, 9829–9838
Publication Date (Web):July 21, 2022
https://doi.org/10.1021/acs.joc.2c00870
Copyright © 2022 American Chemical Society

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    Abstract

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    Bambusurils are macrocyclic molecules that are known for their high binding affinity and selectivity toward anions. Here, we present the preparation of two bambusurils bearing fluorinated substituents and one carboxylic function. These monofunctionalized bambusurils were conjugated with crown ether and cholesterol units. The resulting conjugates were successfully tested in liquid–liquid extraction of inorganic salts and chloride/bicarbonate transport across lipid bilayers.

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    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.joc.2c00870.

    • 1H, 19F, and 13C{1H} NMR spectra, MS spectra of new compounds, and details of extraction and anion transport experiments (PDF).

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    Cited By

    This article is cited by 3 publications.

    1. Arico Del Mauro, Jana Lapešová, Carola Rando, Vladimír Šindelář. Merging Bambus[6]uril and Biotin[6]uril into an Enantiomerically Pure Monofunctionalized Hybrid Macrocycle. Organic Letters 2024, 26 (1) , 106-109. https://doi.org/10.1021/acs.orglett.3c03715
    2. Petr Slávik, Jacopo Torrisi, Pia Jurček, Jan Sokolov, Vladimír Šindelář. Synthesis of Enantiomerically Pure Bambus[6]urils Utilizing Orthogonal Protection of Glycolurils. The Journal of Organic Chemistry 2023, 88 (16) , 11514-11522. https://doi.org/10.1021/acs.joc.3c00667
    3. Luis Martínez‐Crespo, Hennie Valkenier. Transmembrane Transport of Bicarbonate by Anion Receptors. ChemPlusChem 2022, 87 (11) https://doi.org/10.1002/cplu.202200266

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