Pseudorotaxanes formed between secondary dialkylammonium salts and crown ethers

Peter R. Ashton; Ewan J T Chrystal; Peter T. Glink; Stephan Menzer; Cesare Schiavo; Neil Spencer; J. Fraser Stoddart; Peter A. Tasker; Andrew J P White; David J. Williams

doi:10.1002/chem.19960020616

Pseudorotaxanes formed between secondary dialkylammonium salts and crown ethers

Peter R. Ashton, Ewan J T Chrystal, Peter T. Glink, Stephan Menzer, Cesare Schiavo, Neil Spencer, J. Fraser Stoddart^*, Peter A. Tasker, Andrew J P White, David J. Williams

^*Corresponding author for this work

Chemistry

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

340 Scopus citations

Abstract

A very simple self-assembling system, which produces inclusion complexes with pseudorotaxane geometries, is described. The self-assembly of eight pseudorotaxanes with a range of stoichiometries - 1:1, 1:2, 2:1, and 2:2 (host: guest) - has been achieved. These pseudorotaxanes self-assemble from readily available components - well-known crown ethers, such as dibenzo[24]crown-8 and bis-p-phenylene[34]crown-10, and secondary dialkylammonium hexafluorophosphate salts, such as (PhCH₂)₂-NH₂⁺ PF ₆^- and (MBu)₂NH₂⁺PF ₆^- - and have been characterized not only in the solid state, but also in solution and in the "gas phase". The pseudorotaxanes are stabilized largely by hydrogen-bonding interactions and, in some instances, by aryl-aryl interactions.

Original language	English (US)
Pages (from-to)	709-728
Number of pages	20
Journal	Chemistry - A European Journal
Volume	2
Issue number	6
DOIs	https://doi.org/10.1002/chem.19960020616
State	Published - 1996

Keywords

Crown ethers
Dialkylammonium salts
Hydrogen bonding
Molecular recognition
Pseudorotaxanes
Self-assembly

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1002/chem.19960020616

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title = "Pseudorotaxanes formed between secondary dialkylammonium salts and crown ethers",

abstract = "A very simple self-assembling system, which produces inclusion complexes with pseudorotaxane geometries, is described. The self-assembly of eight pseudorotaxanes with a range of stoichiometries - 1:1, 1:2, 2:1, and 2:2 (host: guest) - has been achieved. These pseudorotaxanes self-assemble from readily available components - well-known crown ethers, such as dibenzo[24]crown-8 and bis-p-phenylene[34]crown-10, and secondary dialkylammonium hexafluorophosphate salts, such as (PhCH2)2-NH2+ PF 6- and (MBu)2NH2+PF 6- - and have been characterized not only in the solid state, but also in solution and in the {"}gas phase{"}. The pseudorotaxanes are stabilized largely by hydrogen-bonding interactions and, in some instances, by aryl-aryl interactions.",

keywords = "Crown ethers, Dialkylammonium salts, Hydrogen bonding, Molecular recognition, Pseudorotaxanes, Self-assembly",

author = "Ashton, {Peter R.} and Chrystal, {Ewan J T} and Glink, {Peter T.} and Stephan Menzer and Cesare Schiavo and Neil Spencer and Stoddart, {J. Fraser} and Tasker, {Peter A.} and White, {Andrew J P} and Williams, {David J.}",

year = "1996",

doi = "10.1002/chem.19960020616",

language = "English (US)",

volume = "2",

pages = "709--728",

journal = "Chemistry - A European Journal",

issn = "0947-6539",

publisher = "Wiley-VCH Verlag",

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T1 - Pseudorotaxanes formed between secondary dialkylammonium salts and crown ethers

AU - Ashton, Peter R.

AU - Chrystal, Ewan J T

AU - Glink, Peter T.

AU - Menzer, Stephan

AU - Schiavo, Cesare

AU - Spencer, Neil

AU - Stoddart, J. Fraser

AU - Tasker, Peter A.

AU - White, Andrew J P

AU - Williams, David J.

PY - 1996

Y1 - 1996

N2 - A very simple self-assembling system, which produces inclusion complexes with pseudorotaxane geometries, is described. The self-assembly of eight pseudorotaxanes with a range of stoichiometries - 1:1, 1:2, 2:1, and 2:2 (host: guest) - has been achieved. These pseudorotaxanes self-assemble from readily available components - well-known crown ethers, such as dibenzo[24]crown-8 and bis-p-phenylene[34]crown-10, and secondary dialkylammonium hexafluorophosphate salts, such as (PhCH2)2-NH2+ PF 6- and (MBu)2NH2+PF 6- - and have been characterized not only in the solid state, but also in solution and in the "gas phase". The pseudorotaxanes are stabilized largely by hydrogen-bonding interactions and, in some instances, by aryl-aryl interactions.

AB - A very simple self-assembling system, which produces inclusion complexes with pseudorotaxane geometries, is described. The self-assembly of eight pseudorotaxanes with a range of stoichiometries - 1:1, 1:2, 2:1, and 2:2 (host: guest) - has been achieved. These pseudorotaxanes self-assemble from readily available components - well-known crown ethers, such as dibenzo[24]crown-8 and bis-p-phenylene[34]crown-10, and secondary dialkylammonium hexafluorophosphate salts, such as (PhCH2)2-NH2+ PF 6- and (MBu)2NH2+PF 6- - and have been characterized not only in the solid state, but also in solution and in the "gas phase". The pseudorotaxanes are stabilized largely by hydrogen-bonding interactions and, in some instances, by aryl-aryl interactions.

KW - Crown ethers

KW - Dialkylammonium salts

KW - Hydrogen bonding

KW - Molecular recognition

KW - Pseudorotaxanes

KW - Self-assembly

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DO - 10.1002/chem.19960020616

M3 - Article

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SN - 0947-6539

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EP - 728

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 6

ER -

Pseudorotaxanes formed between secondary dialkylammonium salts and crown ethers

Abstract

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