En route to a molecular sheaf: Active metal template synthesis of a [3]rotaxane with two axles threaded through one ring

Hei Man Cheng, David A. Leigh*, Francesca Maffei, Paul R. McGonigal, Alexandra M.Z. Slawin, Jhenyi Wu

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review


We report that a 2,2′:6′,2″-terpyridylmacrocycle-Ni complex can efficiently mediate the threading of two alkyl chains with bulky end groups in an active metal template sp3-carbon-to-sp 3-carbon homocoupling reaction, resulting in a rare example of a doubly threaded [3]rotaxane in up to 51% yield. The unusual architecture is confirmed by X-ray crystallography (the first time that a one-ring-two-thread [3]rotaxane has been characterized in the solid state) and is found to be stable with respect to dethreading despite the large ring size of the macrocycle. Through such active template reactions, in principle, a macrocycle should be able to assemble as many axles in its cavity as the size of the ring and the stoppers will allow. A general method for threading multiple axles through a macrocycle adds significantly to the tools available for the synthesis of different types of rotaxane architectures.

Original languageEnglish
Pages (from-to)12298-12303
Number of pages6
JournalJournal of the American Chemical Society
Issue number31
Publication statusPublished - 10 Aug 2011

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