6533b7ddfe1ef96bd1273fe7

RESEARCH PRODUCT

Polyether-bridged cyclophanes incorporating bisphenol A units as neutral receptors for quats: synthesis, molecular structure and binding properties

Daniele MancinettiElena NicolettiLuigi MandoliniKari RissanenAntonella Dalla CortMaija Nissinen

subject

TetramethylammoniumBisphenol AStereochemistryOrganic ChemistrySupramolecular chemistryCrystal structureCrystallographychemistry.chemical_compoundMolecular recognitionchemistryMoleculePhysical and Theoretical ChemistryReceptorCyclophane

description

Two novel neutral polyoxyethylene bridged cyclophanes (2a and 2b) incorporating bisphenol A units were synthesized and characterized by means of x-ray crystal structure determination. The binding properties of 2a and 2b toward tetramethylammonium, N-methylpyridinium, and acetylcholine cations were evaluated by means of 1H NMR spectroscopy. Consistent with indications provided by the molecular structure, the cavity in the basket-like cyclophanes is large enough to accommodate the given guest cations conveniently. Circumstantial evidence was obtained that 1,1,2,2-tetrachloroethane is too large to enter the cavity of the smaller cyclophane 2a, but can be included in the cavity of the larger cyclophane 2b. Copyright © 2001 John Wiley & Sons, Ltd.

https://doi.org/10.1002/poc.380