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Issue 13, 2017
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Rapidly accessible “click” rotaxanes utilizing a single amide hydrogen bond templating motif

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Abstract

The synthesis of hydrogen bond templated rotaxanes using the CuAAC click reaction has been achieved in yields of up to 47%, employing near stoichiometric equivalents of macrocycle and readily prepared azide and alkyne half-axle components. Interlocked structure formation has been confirmed by NMR spectroscopy and mass spectrometry. Density functional theory calculations support 1H NMR spectroscopic analysis that the macrocycle resides over the amide of the axle component, rather than the newly formed triazole, as a result of more favourable hydrogen bond interactions.

Graphical abstract: Rapidly accessible “click” rotaxanes utilizing a single amide hydrogen bond templating motif

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Article information


Submitted
06 Feb 2017
Accepted
06 Mar 2017
First published
06 Mar 2017

This article is Open Access

Org. Biomol. Chem., 2017,15, 2797-2803
Article type
Paper

Rapidly accessible “click” rotaxanes utilizing a single amide hydrogen bond templating motif

B. E. Fletcher, M. J. G. Peach and N. H. Evans, Org. Biomol. Chem., 2017, 15, 2797
DOI: 10.1039/C7OB00284J

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