Host-guest assembly of pyridinium-conjugated calix[4]arene via cation-π interaction

Shinsuke Ishihara, Shinji Takeoka

    Research output: Contribution to journalArticle

    34 Citations (Scopus)

    Abstract

    25-(4-Pyridiniumbutoxy)-26,27,28-trihydroxycalix[4]arene bromide 1 was designed to have both host and guest units in one molecule, and was assembled to become an oligomer via a cation-π interaction. X-ray diffraction (XRD) crystallographic study of 1 revealed that it oriented in a one-dimensional structure. Titrimetric 1H NMR analysis and electrospray ionization mass spectrometry (ESI-MS) analysis indicated that 1 formed an oligomer in solution, and the restraint of the segmental motion would lead to the stabilization of the cation-π interaction compared with a bi-molecular complex composed of 25,26,27,28-tetrahydroxycalix[4]arene and N-butylpyridinium bromide.

    Original languageEnglish
    Pages (from-to)181-184
    Number of pages4
    JournalTetrahedron Letters
    Volume47
    Issue number2
    DOIs
    Publication statusPublished - 2006 Jan 9

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    Keywords

    • Calixarene
    • Cation-π interaction
    • Host-guest chemistry
    • Molecular recognition
    • Supramolecular chemistry

    ASJC Scopus subject areas

    • Biochemistry
    • Organic Chemistry
    • Drug Discovery

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