Guest Encapsulation and Self-Assembly of Molecular Capsules in Polar Solvents via Multiple Ionic Interactions
- 17 May 2002
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 124 (23) , 6569-6575
- https://doi.org/10.1021/ja012058z
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.Keywords
This publication has 34 references indexed in Scilit:
- “Flexiball” Toolkit: A Modular Approach to Self-Assembling CapsulesJournal of the American Chemical Society, 2001
- Cavitand−PorphyrinsJournal of the American Chemical Society, 2001
- Template Effects in the Formation of a Tetramethylene-Bridged HemicarceplexJournal of the American Chemical Society, 2000
- Calix[4]arene-Based Receptors with Hydrogen-Bonding Groups Immersed into a Large CavityThe Journal of Organic Chemistry, 1998
- A Soluble C60 Graphite SegmentAngewandte Chemie International Edition in English, 1998
- NMR Studies of the Reversible Dimerization and Guest Exchange Processes of Tetra Urea Calix[4]arenes Using a Derivative with Lower SymmetryJournal of the American Chemical Society, 1997
- Aμ4-Peroxo Complex of Antimony: Synthesis and Structure of(o-Tol2SbO)4(O2)2Angewandte Chemie International Edition in English, 1997
- Calix[4]arene‐Based (Hemi)carcerands and Carceplexes: Synthesis, Functionalization, and Molecular Modeling StudyChemistry – A European Journal, 1997
- Acceleration of a Diels–Alder reaction by a self-assembled molecular capsuleNature, 1997
- Control of Self-Assembly and Reversible Encapsulation of Xenon in a Self-Assembling Dimer by Acid-Base ChemistryJournal of the American Chemical Society, 1995