Triply Threaded [4]Rotaxanes

Danon, J.J.; Leigh, D.A.; McGonigal, P.R.; Ward, J.W.; Wu, J.

doi:10.1021/jacs.6b07733

Triply Threaded [4]Rotaxanes

Danon, J.J.; Leigh, D.A.; McGonigal, P.R.; Ward, J.W.; Wu, J.

Authors

J.J. Danon

D.A. Leigh

Dr Paul Mcgonigal paul.mcgonigal@durham.ac.uk
Academic Visitor

J.W. Ward

J. Wu

Abstract

[4]Rotaxanes featuring three axles threaded through a single ring have been prepared through active metal template synthesis. Nickel-catalyzed sp3-sp3 homocouplings of alkyl bromide ‘half threads’ through 37- and 38-membered 2,2':6',2"-terpyridyl macrocycles generates triply-threaded [4]rotaxanes in up to 11 % yield. An analogous 39-membered macrocycle produced no rotaxane products under similar conditions. The constitutions of the [4]rotaxanes were determined by NMR spectroscopy and mass spectrometry. Doubly-threaded [3]rotaxanes were also obtained from the reactions but no [2]rotaxanes were isolated, suggesting that upon demetallation the axle of a singly-threaded rotaxane can slip through a macrocycle that is sufficiently large to accommodate three threads.

Citation

Danon, J., Leigh, D., McGonigal, P., Ward, J., & Wu, J. (2016). Triply Threaded [4]Rotaxanes. Journal of the American Chemical Society, 138(38), 12643-12647. https://doi.org/10.1021/jacs.6b07733

Journal Article Type	Article
Acceptance Date	Aug 29, 2016
Online Publication Date	Aug 29, 2016
Publication Date	Sep 28, 2016
Deposit Date	Sep 4, 2016
Publicly Available Date	Sep 5, 2016
Journal	Journal of the American Chemical Society
Print ISSN	0002-7863
Electronic ISSN	1520-5126
Publisher	American Chemical Society
Peer Reviewed	Peer Reviewed
Volume	138
Issue	38
Pages	12643-12647
DOI	https://doi.org/10.1021/jacs.6b07733

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