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

    Research output: Contribution to journalArticleAcademicpeer-review

    125 Citations (Scopus)

    Abstract

    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
    Volume124
    Issue number23
    DOIs
    Publication statusPublished - 2002

    Keywords

    • IR-37952
    • METIS-206211

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