Evolution of Organized Lariat Ether Alcohol and Diol Hydrate Macrostructures in the Solid State

Uriel Olsher; N. Kent Dalley; Felix Frolow; Gil Shoham; Richard A. Bartsch

doi:10.1023/A:1024512416378

Evolution of Organized Lariat Ether Alcohol and Diol Hydrate Macrostructures in the Solid State

Uriel Olsher, N. Kent Dalley, Felix Frolow, Gil Shoham, Richard A. Bartsch^*

^*Corresponding author for this work

Institute of Chemistry

Research output: Contribution to journal › Article › peer-review

1 Scopus citations

Abstract

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.

Original language	English
Pages (from-to)	251-255
Number of pages	5
Journal	Journal of Inclusion Phenomena
Volume	45
Issue number	3-4
DOIs	https://doi.org/10.1023/A:1024512416378
State	Published - Apr 2003

Bibliographical note

Funding 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.

Keywords

Crystal growth
Dibenzo-14-crown-4 alcohols and diols
Hydrogen bonding
Solvent effects

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abstract = "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.",

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author = "Uriel Olsher and Dalley, {N. Kent} and Felix Frolow and Gil Shoham and Bartsch, {Richard A.}",

note = "Funding 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.",

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AU - Frolow, Felix

AU - Shoham, Gil

AU - Bartsch, Richard A.

N1 - Funding 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.

PY - 2003/4

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N2 - 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.

AB - 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.

KW - Crystal growth

KW - Dibenzo-14-crown-4 alcohols and diols

KW - Hydrogen bonding

KW - Solvent effects

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Evolution of Organized Lariat Ether Alcohol and Diol Hydrate Macrostructures in the Solid State

Abstract

Bibliographical note

Keywords

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