Rights statement: © Royal Society of Chemistry 2017
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Research output: Contribution to Journal/Magazine › Journal article › peer-review
Research output: Contribution to Journal/Magazine › Journal article › peer-review
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TY - JOUR
T1 - Rapidly accessible "click" rotaxanes utilizing a single amide hydrogen bond templating motif
AU - Fletcher, Beth Emma
AU - Peach, Michael Joseph George
AU - Evans, Nicholas Henley
N1 - © Royal Society of Chemistry 2017
PY - 2017/4/7
Y1 - 2017/4/7
N2 - 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.
AB - 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.
U2 - 10.1039/C7OB00284J
DO - 10.1039/C7OB00284J
M3 - Journal article
VL - 15
SP - 2797
EP - 2803
JO - Organic and Biomolecular Chemistry
JF - Organic and Biomolecular Chemistry
SN - 1477-0520
IS - 13
ER -