A pseudorotaxane formed from a cucurbit[7]uril wheel and a bioinspired molecular axle with pH, light and redox-responsive properties

Research output: Contribution to journalConference article

Abstract

A pH-, light- and redox-responsive flavylium-bipyridinium molecular dyad (bioinspired in natural anthocyanins) was synthesized and employed to devise a pseudorotaxane with the macrocycle cucurbit[7]uril (CB7) in aqueous solution. The inclusion complex was characterized by UV-Vis absorption, fluorescence emission, NMR and electrochemical techniques which demonstrate formation of a stable binary complex between the dyad and CB7 both under acidic and neutral conditions. It is noteworthy that the flavylium-bipyridinium tricationic dyad is only stable in highly acidic media, undergoing a reversible hydration reaction at slightly acidic or neutral pH to give a trans-chalcone-bipyridinium dication. 1H NMR experiments showed that in this last species the CB7 binds to the bipyridinium unit while in the tricationic species the macrocycle is positioned between the flavylium and the bipyridinium moieties. The different location of the CB7 wheel in the two dyad states allows control of the shuttling movement using light and pH stimuli that trigger the interconversion between these two species.

Original languageEnglish
Pages (from-to)301-313
JournalPure and Applied Chemistry
Volume92
Issue number2
Early online date25 Oct 2019
DOIs
Publication statusPublished - 25 Feb 2020
Event4th International Conference on Bioinspired and Biobased Chemistry and Materials (NICE) - Nice, France
Duration: 14 Oct 201717 Oct 2018

Keywords

  • flavylium photoswitches
  • molecular machines
  • NICE-2018
  • photochemistry
  • supramolecular chemistry

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