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3-(Dicyanomethylidene)indan-1-one-Functionalized Calix[4]arene–Calix[4]pyrrole Hybrid: An Ion-Pair Sensor for Cesium Salts

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    3-(Dicyanomethylidene)indan-1-one-Functionalized Calix[4]arene–Calix[4]pyrrole Hybrid: An Ion-Pair Sensor for Cesium Salts
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    † Department of Chemistry, The University of Texas at Austin, 105 East 24th Street, Stop A5300, Austin, Texas 78712-1224, United States
    ‡ Department of Chemistry and Research Institute of Natural Science, Gyeongsang National University, Jinju 660-701, Korea
    *E-mail: [email protected]
    *E-mail: [email protected]
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    Organic Letters

    Cite this: Org. Lett. 2016, 18, 17, 4396–4399
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    https://doi.org/10.1021/acs.orglett.6b02155
    Published August 17, 2016
    Copyright © 2016 American Chemical Society
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    Abstract

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    A chromogenic calix[4]arene–calix[4]pyrrole hybrid ion pair receptor bearing an indane substituent at a β-pyrrolic position has been prepared. On the basis of solution-phase UV–vis spectroscopic analysis and 1H NMR spectroscopic studies carried out in 10% methanol in chloroform, receptor 1 is able to bind only cesium ion pairs (e.g., CsF, CsCl, and CsNO3) but not the constituent cesium cation (as its perchlorate salt) or the F–, Cl–, or NO3– anions (as the tetrabutylammonium salts). It thus displays rudimentary AND logic gate behavior. Receptor 1 shows a colorimetric response to cesium ion pairs under conditions of solid–liquid (nitrobenzene) and liquid–liquid (D2O–nitrobenzene-d5) extraction.

    Copyright © 2016 American Chemical Society

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    Organic Letters

    Cite this: Org. Lett. 2016, 18, 17, 4396–4399
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.orglett.6b02155
    Published August 17, 2016
    Copyright © 2016 American Chemical Society
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