Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 20, Issue 37, Pages 11750-11759Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201403531
Keywords
calix[4]pyrrole; cyclic hexamers; ion-pair receptors; self-assembly; supramolecular polymers
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Funding
- Office of Basic Energy Sciences, U.S. Department of Energy (DOE) [DE-FG02-01ER15186]
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A new approach to the construction of self-assembled structures is reported that is based on ion-pair recognition. Towards this end, the calix[4]pyrrole naphthocrown-4 hybrid structures 2 and 3 were prepared. These multitopic receptors contain recognition sites for both anions and cations. On the basis of solution-phase H-1 NMR spectroscopic analysis and solid-state single-crystal X-ray diffraction structural studies, it was established that receptors 2 and 3 are able to bind specific ion pairs with high selectivity via different binding modes. In the case of CsF and CsCl, the ion-pair complexes formed from receptors 2 and 3 were found to self-assemble to produce either linear supramolecular polymeric crystalline solids or nanotube-like cyclic hexamers depending on the specific choice of ion pairs and crystallization solvents. Proton NMR studies provided evidence for solution-phase self-association in organic media.
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