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

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Published
<mark>Journal publication date</mark>7/04/2017
<mark>Journal</mark>Organic and Biomolecular Chemistry
Issue number13
Volume15
Number of pages7
Pages (from-to)2797-2803
<mark>State</mark>Published
Early online date9/03/17
<mark>Original language</mark>English

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.

Bibliographic note

© Royal Society of Chemistry 2017