Triply Threaded [4]Rotaxanes

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

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