Anion-free bambus[6]uril and its supramolecular properties

Jan Svec, Michal Dusek, Karla Fejfarova, Peter Stacko, Petr Klán, Angel E. Kaifer, Wei Li, Edita Hudeckova, Vladimir Sindelar

Research output: Contribution to journalArticle

65 Scopus citations

Abstract

Methods for the preparation of anion-free bambus[6]uril (BU6) are presented. They are based on the oxidation of iodide anion, which is bound inside the macrocycle, utilizing dark oxidation by hydrogen peroxide or photooxidation in the presence of titanium dioxide. Anion-free BU6 was found to be insoluble in any of the investigated solvents; however, it dissolves in methanol/chloroform (1:1) or acetonitrile/water (1:1) mixtures in the presence of the tetrabutylammonium salt of a suitable anion. The association constants with halide ions, BF4-, NO3-, and CN-, were measured by 1H NMR spectroscopy. The highest association constant (8.9×105 M-1) was found for the 1:1 complex of BU6 with I- in acetonitrile/water mixture. A number of crystal structures of BU6 complexes with various anions were obtained. The influence of the anion size on the macrocycle diameter is discussed together with an unusual arrangement of the macrocycles into separate layers.

Original languageEnglish (US)
Pages (from-to)5605-5612
Number of pages8
JournalChemistry - A European Journal
Volume17
Issue number20
DOIs
StatePublished - May 9 2011

Keywords

  • anion receptors
  • halides
  • host-guest systems
  • macrocycles
  • supramolecular chemistry

ASJC Scopus subject areas

  • Chemistry(all)

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    Svec, J., Dusek, M., Fejfarova, K., Stacko, P., Klán, P., Kaifer, A. E., Li, W., Hudeckova, E., & Sindelar, V. (2011). Anion-free bambus[6]uril and its supramolecular properties. Chemistry - A European Journal, 17(20), 5605-5612. https://doi.org/10.1002/chem.201003683