Skip to main content

Research Repository

Advanced Search

Triply Threaded [4]Rotaxanes

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

Triply Threaded [4]Rotaxanes Thumbnail


J.J. Danon

D.A. Leigh

J.W. Ward

J. Wu


[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.


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.

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


Accepted Journal Article (17.7 Mb)

Copyright Statement
ACS AuthorChoice - This is an open access article published under a Creative Commons Attribution (CC-BY) License, which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.

You might also like

Downloadable Citations