Self-assembling [2]- And [3]rotaxanes from secondary dialkylammonium salts and crown ethers

Peter R. Ashton; Peter T. Glink; J. Fraser Stoddart; Peter A. Tasker; Andrew J P White; David J. Williams

doi:10.1002/chem.19960020617

Self-assembling [2]- And [3]rotaxanes from secondary dialkylammonium salts and crown ethers

Peter R. Ashton, Peter T. Glink, 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

173 Scopus citations

Abstract

The self-assembly of three new rotaxanes - two [2]rotaxanes and a [3]rotaxane - formed by a "threading followed by stoppering" approach is described. These template-directed syntheses rely on the formation of pseudorotaxane intermediates, which self-assemble in solution from functionalized secondary dialkylammonium hexafluorophosphate threads and macrocyclic polyether rings (either dibenzo[24]crown-8 or its asymmetric constitutional isomer). The stoppers - substituted 1,2,3-triazoles - were created by thermally allowed 1,3-dipolar cycloadditions between azido groups, which terminate the threads, and di-tert-butyl acetylenedicarboxylate.

Original language	English (US)
Pages (from-to)	729-736
Number of pages	8
Journal	Chemistry - A European Journal
Volume	2
Issue number	6
DOIs	https://doi.org/10.1002/chem.19960020617
State	Published - 1996

Keywords

Merlocking molecules
Molecular recognition
Pseudorotaxanes
Rotaxanes
Template syntheses

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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title = "Self-assembling [2]- And [3]rotaxanes from secondary dialkylammonium salts and crown ethers",

abstract = "The self-assembly of three new rotaxanes - two [2]rotaxanes and a [3]rotaxane - formed by a {"}threading followed by stoppering{"} approach is described. These template-directed syntheses rely on the formation of pseudorotaxane intermediates, which self-assemble in solution from functionalized secondary dialkylammonium hexafluorophosphate threads and macrocyclic polyether rings (either dibenzo[24]crown-8 or its asymmetric constitutional isomer). The stoppers - substituted 1,2,3-triazoles - were created by thermally allowed 1,3-dipolar cycloadditions between azido groups, which terminate the threads, and di-tert-butyl acetylenedicarboxylate.",

keywords = "Merlocking molecules, Molecular recognition, Pseudorotaxanes, Rotaxanes, Template syntheses",

author = "Ashton, {Peter R.} and Glink, {Peter T.} and Stoddart, {J. Fraser} and Tasker, {Peter A.} and White, {Andrew J P} and Williams, {David J.}",

year = "1996",

doi = "10.1002/chem.19960020617",

language = "English (US)",

volume = "2",

pages = "729--736",

journal = "Chemistry - A European Journal",

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T1 - Self-assembling [2]- And [3]rotaxanes from secondary dialkylammonium salts and crown ethers

AU - Ashton, Peter R.

AU - Glink, Peter T.

AU - Stoddart, J. Fraser

AU - Tasker, Peter A.

AU - White, Andrew J P

AU - Williams, David J.

PY - 1996

Y1 - 1996

N2 - The self-assembly of three new rotaxanes - two [2]rotaxanes and a [3]rotaxane - formed by a "threading followed by stoppering" approach is described. These template-directed syntheses rely on the formation of pseudorotaxane intermediates, which self-assemble in solution from functionalized secondary dialkylammonium hexafluorophosphate threads and macrocyclic polyether rings (either dibenzo[24]crown-8 or its asymmetric constitutional isomer). The stoppers - substituted 1,2,3-triazoles - were created by thermally allowed 1,3-dipolar cycloadditions between azido groups, which terminate the threads, and di-tert-butyl acetylenedicarboxylate.

AB - The self-assembly of three new rotaxanes - two [2]rotaxanes and a [3]rotaxane - formed by a "threading followed by stoppering" approach is described. These template-directed syntheses rely on the formation of pseudorotaxane intermediates, which self-assemble in solution from functionalized secondary dialkylammonium hexafluorophosphate threads and macrocyclic polyether rings (either dibenzo[24]crown-8 or its asymmetric constitutional isomer). The stoppers - substituted 1,2,3-triazoles - were created by thermally allowed 1,3-dipolar cycloadditions between azido groups, which terminate the threads, and di-tert-butyl acetylenedicarboxylate.

KW - Merlocking molecules

KW - Molecular recognition

KW - Pseudorotaxanes

KW - Rotaxanes

KW - Template syntheses

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Self-assembling [2]- And [3]rotaxanes from secondary dialkylammonium salts and crown ethers

Abstract

Keywords

ASJC Scopus subject areas

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