Guest encapsulation and self-assembly of molecular capsules in polar solvents via multiple ionic interactions |
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Authors: | Corbellini Francesca Fiammengo Roberto Timmerman Peter Crego-Calama Mercedes Versluis Kees Heck Albert J R Luyten Ingrid Reinhoudt David N |
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Institution: | Laboratory of Supramolecular Chemistry and Technology, MESA+ Research Institute, University of Twente P.O. Box 217, 7500 AE Enschede, The Netherlands. |
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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 calix4]arenes 1a-d and tetrasulfonato calix4]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 10(6) M-1. The system 1a.2 shows binding affinity toward acetylcholine, tetramethylammonium, and N-methylquinuclidinium cations. |
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