Lariat ether alcohols and diols derived from dibenzo-14-crown-4 crystallize in the anhydrous form or as hydrogen-bonded monohydrates or networks depending upon the polyether 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.
Bibliographical noteFunding Information:
This research was supported by the Israel-US Binational Science Foundation (BSF Grant # 94-366, awarded to GS, UO, and RAB). Partial support of this research by The Welch Foundation (Grant D-775 to RAB) is gratefully acknowledged. Appreciation is also expressed to the Office of Basic Energy Sciences of the US Department of Energy (Grant DE-FG02-8GER-13463) and the State of Utah Centers of Excellence Program for partial support of this work.
- Crystal growth
- Dibenzo-14-crown-4 alcohols and diols
- Hydrogen bonding
- Solvent effects