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

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 sp...

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Bibliographic Details
Published inOrganic & biomolecular chemistry Vol. 15; no. 13; pp. 2797 - 2803
Main Authors Fletcher, Beth E., Peach, Michael J. G., Evans, Nicholas H.
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 2017
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
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Summary: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 H-1 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.
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ISSN:1477-0520
1477-0539
DOI:10.1039/c7ob00284j