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

Fletcher, Beth Emma and Peach, Michael Joseph George and Evans, Nicholas Henley (2017) Rapidly accessible "click" rotaxanes utilizing a single amide hydrogen bond templating motif. Organic and Biomolecular Chemistry, 15 (13). pp. 2797-2803. ISSN 1477-0520

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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.

Item Type:
Journal Article
Journal or Publication Title:
Organic and Biomolecular Chemistry
Additional Information:
© Royal Society of Chemistry 2017
Uncontrolled Keywords:
/dk/atira/pure/subjectarea/asjc/1600/1606
Subjects:
ID Code:
85058
Deposited By:
Deposited On:
06 Mar 2017 15:04
Refereed?:
Yes
Published?:
Published
Last Modified:
30 Sep 2020 06:47