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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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Publication details

The article was received on 06 Feb 2017, accepted on 06 Mar 2017, published on 06 Mar 2017 and first published online on 06 Mar 2017


Article type: Paper
DOI: 10.1039/C7OB00284J
Citation: Org. Biomol. Chem., 2017,15, 2797-2803
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    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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