A Redox-Switchable Molecular Zipper

Melissa Dumartin, Mark C. Lipke*, J. Fraser Stoddart

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

19 Scopus citations


The design and synthesis of artificial molecular switches (AMSs) displaying architectures of increased complexity would constitute significant progress in meeting the challenging task of realizing artificial molecular machines (AMMs). Here, we report the synthesis and characterization of a molecular shuttle composed of a cyclobis(paraquat-4,4′-biphenylene) cyclophane ring and a dumbbell incorporating a cyclobis(paraquat-m-phenylene) cyclophane "head" and a bifurcated, tawse-like "tail" composed of two oligoether chains, each containing a 1,5-dioxynaphthalene ring. In its reduced state the ring-in-ring recognition motif, between the meta and para bisradical dicationic cyclophanes (rings), defines the [2]rotaxane, whereas in the oxidized state, the cyclobis(paraquat-4,4′-biphenylene) cyclophane encircles the two 1,5-dioxynaphthalene rings in the bifurcated "tail". The redox-controlled molecular shuttling, which can be likened to the action of a zipper in the macroscopic world, exhibits slow kinetics dampened by the opening and closing of the bifurcated "tail" of the molecular shuttle. Cyclic voltammetry reveals that this slow shuttling is associated with electrochemical hysteresis.

Original languageEnglish (US)
Pages (from-to)18308-18317
Number of pages10
JournalJournal of the American Chemical Society
Issue number45
StatePublished - Nov 13 2019

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry


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