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N-Alkyl ammonium resorcinarene salts: multivalent halogen-bonded deep-cavity cavitands

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Original languageEnglish
Pages (from-to)340-345
Number of pages6
JournalOrganic chemistry frontiers
Issue number4
Publication statusPublished - 2015
Publication typeA1 Journal article-refereed


N-Cyclohexyl ammonium resorcinarene halides, stabilized by an intricate array of hydrogen bonds in a cavitand-like assembly, form multivalent halogen-bonded deep-cavity cavitands with perfluoroiodobenzenes. As observed from the macromolar to infinite concentration range through crystal growth and single crystal X-ray analyses, four 1,4-diiodotetrafluorobenzenes form moderate halogen bonds with the bromides of the N-cyclohexyl ammonium resorcinarene bromides leading to a deep-cavity cavitand-like structure. In this assembly, the N-cyclohexyl ammonium resorcinarene bromide also acts as a guest and sits in the upper cavity of the assembly interacting with the 1,4-diiodotetrafluorobenzene through strong pi center dot center dot center dot pi interactions. Solvent molecules act as guests and are located deep in the cavity of the resorcinarene skeleton. In the millimolar range, H-1 and F-19 NMR spectroscopic analyses confirm halogen bonding in solution. Fast exchange binding of electron rich fluorophores (naphthalene, anthracene and pyrene) in the upper layer of these assemblies was also observed in the millimolar range while in the micromolar range, using fluorescence analysis, no binding of the fluorophores was observed.



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Field of science, Statistics Finland