pH Control on the Sequential Uptake and Release of Organic Cations by Cucurbit[7]uril

Lukas Mikulu, Romana Michalicova, Vivian Iglesias, Mirza A. Yawer, Angel E. Kaifer, Premysl Lubal, Vladimir Sindelar

Research output: Contribution to journalArticle

11 Scopus citations

Abstract

Cucurbit[7]uril (CB7) is a macrocycle with the ability to form the most stable supramolecular complexes in water ever reported for an artificial receptor. Its use for the design of advanced functional materials is, however, very limited because there is no example of a fully reversible CB7 based supramolecular complex enabling repetitious dissociation/association controlled by external stimuli. We report the synthesis of a new ferrocene amino acid that forms with CB7 a 1:1 inclusion complex that is stable in submicromolar concentration at low pH but dissociates at high pH. This reversible process was used for the sequential uptake and release of bispyridinium and antraquinone guests by CB7, which is controlled by adjusting the pH of the solution.

Original languageEnglish (US)
Pages (from-to)2350-2355
Number of pages6
JournalChemistry - A European Journal
Volume23
Issue number10
DOIs
StatePublished - Jan 1 2017

Keywords

  • cage compounds
  • drug delivery
  • macrocycles
  • molecular devices
  • supramolecular chemistry

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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    Mikulu, L., Michalicova, R., Iglesias, V., Yawer, M. A., Kaifer, A. E., Lubal, P., & Sindelar, V. (2017). pH Control on the Sequential Uptake and Release of Organic Cations by Cucurbit[7]uril. Chemistry - A European Journal, 23(10), 2350-2355. https://doi.org/10.1002/chem.201604417