Guest encapsulation and self-assembly of molecular capsules in polar solvents via multiple ionic interactions

F. Corbellini, R. Fiammengo, P. Timmerman, Mercedes Crego Calama, Kees Versluis, Albert J.R. Heck, Ingrid Luyten, David Reinhoudt

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    Herein we report the formation and characterization of a novel type of capsules resulting from the self-association between oppositely charged complementary building blocks in MeOH/H2O. The assembly is based on the interaction between tetraamidinium calix[4]arenes 1a-d and tetrasulfonato calix[4]arene 2. Evidence for the formation of the expected 1:1 assemblies is provided by proton NMR, ESI-MS, and ITC. The association process is fast on the NMR time scale and strongly entropy driven, with association constants in the range of 106 M-1. The system 1a·2 shows binding affinity toward acetylcholine, tetramethylammonium, and N-methylquinuclidinium cations.
    Original languageUndefined
    Pages (from-to)6569-6575
    JournalJournal of the American Chemical Society
    Issue number23
    Publication statusPublished - 2002


    • IR-37952
    • METIS-206211

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