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JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 124, Issue 23, Pages 6569-6575Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja012058z
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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 10(6) M-1. The system 1a.2 shows binding affinity toward acetylcholine, tetramethylammonium, and N-methylquinuclidinium cations.
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