Guest Encapsulation and Self-Assembly of Molecular Capsules in Polar Solvents via Multiple Ionic Interactions

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Corbellini, Francesca and Fiammengo, Roberto and Timmerman, Peter and Crego Calama, Mercedes and Versluis, Kees and Heck, Albert J.R. and Luyten, Ingrid and Reinhoudt, David N. (2002) Guest Encapsulation and Self-Assembly of Molecular Capsules in Polar Solvents via Multiple Ionic Interactions. Journal of the American Chemical Society, 124 (23). pp. 6569-6575. ISSN 0002-7863

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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 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.
Item Type:Article
Copyright:© 2002 American Chemical Society
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Link to this item:http://purl.utwente.nl/publications/37952
Official URL:http://dx.doi.org/10.1021/ja012058z
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Metis ID: 206211