Triply Threaded [4]Rotaxanes

Jonathan J. Danon, David A. Leigh*, Paul R. McGonigal, John W. Ward, Jhenyi Wu

*Corresponding author for this work

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[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 generate 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 demetalation the axle of a singly threaded rotaxane can slip through a macrocycle that is sufficiently large to accommodate three threads.

Original languageEnglish
Pages (from-to)12643-12647
Number of pages5
JournalJournal of the American Chemical Society
Issue number38
Publication statusPublished - 28 Sept 2016

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