A new protocol for rotaxane synthesis

Stuart J. Cantrill; David A. Fulton; Matthew C T Fyfe; J. Fraser Stoddart; Andrew J P White; David J. Williams

doi:10.1016/S0040-4039(99)00555-9

A new protocol for rotaxane synthesis

Stuart J. Cantrill, David A. Fulton, Matthew C T Fyfe, J. Fraser Stoddart^*, Andrew J P White, David J. Williams

^*Corresponding author for this work

Chemistry

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

43 Scopus citations

Abstract

A novel [2]rotaxane was synthesized when an aniline-bearing [2]pseudorotaxane-generated by the hydrogen bond-driven threading of a dibenzylammonium filament through the cavity of the macrocyclic polyether dibenzo[24]crown-8-was stoppered via reaction with a bulky isocyanate. Complete characterization of the [2]rotaxane was accomplished by NMR spectroscopy, mass spectrometry and X-ray crystallography.

Original language	English (US)
Pages (from-to)	3669-3672
Number of pages	4
Journal	Tetrahedron Letters
Volume	40
Issue number	19
DOIs	https://doi.org/10.1016/S0040-4039(99)00555-9
State	Published - May 7 1999

Keywords

Rotaxanes
Self-assembly
Synthetic methods
Template synthesis

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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T1 - A new protocol for rotaxane synthesis

AU - Cantrill, Stuart J.

AU - Fulton, David A.

AU - Fyfe, Matthew C T

AU - Stoddart, J. Fraser

AU - White, Andrew J P

AU - Williams, David J.

PY - 1999/5/7

Y1 - 1999/5/7

N2 - A novel [2]rotaxane was synthesized when an aniline-bearing [2]pseudorotaxane-generated by the hydrogen bond-driven threading of a dibenzylammonium filament through the cavity of the macrocyclic polyether dibenzo[24]crown-8-was stoppered via reaction with a bulky isocyanate. Complete characterization of the [2]rotaxane was accomplished by NMR spectroscopy, mass spectrometry and X-ray crystallography.

AB - A novel [2]rotaxane was synthesized when an aniline-bearing [2]pseudorotaxane-generated by the hydrogen bond-driven threading of a dibenzylammonium filament through the cavity of the macrocyclic polyether dibenzo[24]crown-8-was stoppered via reaction with a bulky isocyanate. Complete characterization of the [2]rotaxane was accomplished by NMR spectroscopy, mass spectrometry and X-ray crystallography.

KW - Rotaxanes

KW - Self-assembly

KW - Synthetic methods

KW - Template synthesis

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JO - Tetrahedron Letters

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