Calix[4]arenes, molecular platforms for supramolecular structures

L.C. Groenen, D.N. Reinhoudt

    Research output: Chapter in Book/Report/Conference proceedingChapterAcademic

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    Abstract

    A new strategy for the synthesis of receptor molecules comprises the combination of medium-sized molecules to which functional groups for intermolecular interactions can be attached. Most efforts concern the functionalization of calix[4]arenes, but other building blocks like cyclodextrins and octols are used as well. Selective mono-, 1,2-di, 1,3-di-, and tetraalkylation of calix[4]arenes can be achieved by variation of the alkylation conditions. The calix[4]arenes can be (selectively) functionalized at the “upper rim” by a variety of methods including ipso-nitration. Combination of the calix[4]arenes with crown ethers to calixcrowns gave receptors with a high K+/Na+-selectivity and with terphenyls calixspherands were obtained that form kinetically stable complexes with Na+, K+ and Rb+. Bridging of calix[4]arene with a salophene moiety gave a receptor for urea that can effectively transport urea through a supported liquid membrane. Calix[4]arenes can be combined covalently to double and triple calixarenes and with selectively functionalized octols. When substituted with hydrogen bond donors and acceptors like 2-pyridone, calixarenes undergo self-association to larger aggregrates.
    Original languageEnglish
    Title of host publicationSupramolecular Chemistry
    EditorsV. Balzani, L. de Cola
    Place of PublicationDordrecht
    PublisherKluwer Academic Publishers
    Pages51-70
    ISBN (Print)9780792317593
    DOIs
    Publication statusPublished - 1992

    Publication series

    NameNATO ASI Series C: Mathematical and Physical Sciences
    PublisherKluwer Academic Publishers
    Volume371

    Fingerprint

    Calixarenes
    Urea
    Crown Ethers
    Nitration
    Liquid membranes
    Molecules
    Alkylation
    Cyclodextrins
    Functional groups
    Hydrogen bonds
    Association reactions

    Keywords

    • IR-13003
    • METIS-107184

    Cite this

    Groenen, L. C., & Reinhoudt, D. N. (1992). Calix[4]arenes, molecular platforms for supramolecular structures. In V. Balzani, & L. de Cola (Eds.), Supramolecular Chemistry (pp. 51-70). (NATO ASI Series C: Mathematical and Physical Sciences; Vol. 371). Dordrecht: Kluwer Academic Publishers. https://doi.org/10.1007/978-94-011-2492-8_4
    Groenen, L.C. ; Reinhoudt, D.N. / Calix[4]arenes, molecular platforms for supramolecular structures. Supramolecular Chemistry. editor / V. Balzani ; L. de Cola. Dordrecht : Kluwer Academic Publishers, 1992. pp. 51-70 (NATO ASI Series C: Mathematical and Physical Sciences).
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    Groenen, LC & Reinhoudt, DN 1992, Calix[4]arenes, molecular platforms for supramolecular structures. in V Balzani & L de Cola (eds), Supramolecular Chemistry. NATO ASI Series C: Mathematical and Physical Sciences, vol. 371, Kluwer Academic Publishers, Dordrecht, pp. 51-70. https://doi.org/10.1007/978-94-011-2492-8_4

    Calix[4]arenes, molecular platforms for supramolecular structures. / Groenen, L.C.; Reinhoudt, D.N.

    Supramolecular Chemistry. ed. / V. Balzani; L. de Cola. Dordrecht : Kluwer Academic Publishers, 1992. p. 51-70 (NATO ASI Series C: Mathematical and Physical Sciences; Vol. 371).

    Research output: Chapter in Book/Report/Conference proceedingChapterAcademic

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    AB - A new strategy for the synthesis of receptor molecules comprises the combination of medium-sized molecules to which functional groups for intermolecular interactions can be attached. Most efforts concern the functionalization of calix[4]arenes, but other building blocks like cyclodextrins and octols are used as well. Selective mono-, 1,2-di, 1,3-di-, and tetraalkylation of calix[4]arenes can be achieved by variation of the alkylation conditions. The calix[4]arenes can be (selectively) functionalized at the “upper rim” by a variety of methods including ipso-nitration. Combination of the calix[4]arenes with crown ethers to calixcrowns gave receptors with a high K+/Na+-selectivity and with terphenyls calixspherands were obtained that form kinetically stable complexes with Na+, K+ and Rb+. Bridging of calix[4]arene with a salophene moiety gave a receptor for urea that can effectively transport urea through a supported liquid membrane. Calix[4]arenes can be combined covalently to double and triple calixarenes and with selectively functionalized octols. When substituted with hydrogen bond donors and acceptors like 2-pyridone, calixarenes undergo self-association to larger aggregrates.

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    EP - 70

    BT - Supramolecular Chemistry

    A2 - Balzani, V.

    A2 - de Cola, L.

    PB - Kluwer Academic Publishers

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    ER -

    Groenen LC, Reinhoudt DN. Calix[4]arenes, molecular platforms for supramolecular structures. In Balzani V, de Cola L, editors, Supramolecular Chemistry. Dordrecht: Kluwer Academic Publishers. 1992. p. 51-70. (NATO ASI Series C: Mathematical and Physical Sciences). https://doi.org/10.1007/978-94-011-2492-8_4