Abstract
Lariat ether alcohols and diols derived from dibenzo-14-crown-4crystallize in the anhydrous form or as hydrogen-bondedmonohydrates or networks depending upon thepolyether ring substitutents and the composition of the aqueous organic crystallization solvent. Supramolecular structures are created when the lariat ether alcohol sym-(hydroxy)dibenzo-14-crown-4 (1) with ``sticky ends'' of ether oxygens and hydroxyl protons, hydrogen bond to each other via bridging water molecules to form three-dimensional networks. For crystallization of 1 from 30% aqueous acetonitrile, this self-association is sufficiently strong to spontaneously generate a supramolecular structure with water channels.
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