Selective Binding of Imidazolium Cations in Building Multi-Component Layers

Irene Ling, Yatimah Alias, Alexandre Sobolev, Lindsay Byrne, Colin Raston

    Research output: Contribution to journalArticlepeer-review

    16 Citations (Scopus)

    Abstract

    Addition of l-alkyl-3-methyl-imidazolium (Cn-mim) cations 3-5 to a mixture of bis-phosphonium cation 2 and sodium p-sulfonatocalix[4]arene (1) in the presence of lanthanide ions results in the selective binding of an imidazolium cation into the cavity of the calixarene. The result is a multi-layered solid material with an inherently flexible interplay of the components. Incorporating ethyl-, n-butyl- or nhexyl-mim cations into the multi-layers results in significant perturbation of the structure, the most striking effect is the tilting of the plane of the bowl-shaped calixarene relative to the plane of the multi-layer, with tilt angles of 7.2, 28.9 and 65.5°, respectively. The lanthanide ions facilitate complexation, but are not incorporated into the structures and, in all cases, the calixarene takes on a 5- charge, with one of the lower-rim phenolic groups deprotonated. ROESY NMR experiments and other 1H NMR spectroscopy studies establish the formation of 1:1 supermolecules of Cn-mim and calixarene, regardless of the ratio of the two components, and indicate that the supermolecules undergo rapid exchange on the NMR spectroscopy timescale.

    Original languageEnglish
    Pages (from-to)6973-6982
    Number of pages10
    JournalChemistry-A European Journal
    Volume16
    Issue number23
    DOIs
    Publication statusPublished - 18 Jun 2010

    Keywords

    • Bis-phosphonium cations
    • Calixarenes
    • Host-guest systems
    • Imidazolium cations

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