A water-soluble pH-triggered molecular switch

Sergio Grunder, Psaras L. McGrier, Adam C. Whalley, Megan M. Boyle, Charlotte Stern, J Fraser Stoddart*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

59 Scopus citations

Abstract

A bistable donor-acceptor [2]catenane, which is composed of a crown ether containing a hydroquinone unit and a 1,5-diaminonaphthalene unit, interlocked mechanically by cyclobis(paraquat-p-phenylene) as its tetrachloride, exists as a mixture of translational isomers, both in the solid state and in aqueous solution. UV/vis and 1H NMR spectroscopies demonstrate that this isomeric mixture can be switched in water in the presence of hydrochloric acid to afford a single diprotonated derivative in which only the hydroquinone unit resides inside the cavity of the tetracationic cyclophane. Treatment with 1,4-diazabicyclo[2.2.2]octane resets the molecular switch.

Original languageEnglish (US)
Pages (from-to)17691-17694
Number of pages4
JournalJournal of the American Chemical Society
Volume135
Issue number47
DOIs
StatePublished - Nov 27 2013

ASJC Scopus subject areas

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

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