Inclusion complex formation of ionic liquids and other cationic organic compounds with cucurbit[7]uril studied by 4',6-diamidino-2-phenylindole fluorescent probe

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Abstract

The encapsulation of 4',6-diamidino-2-phenylindole (DAPI) in the cucurbit[7]uril (CB7) cavity was studied by absorption, fluorescence, and NMR spectroscopic methods in aqueous solution. The profound change in the fluorescence characteristics was attributed to the formation of a very stable 1:1 inclusion complex. Three independent methods provided (1.1 ±0.1) x 107 M-1 value for the binding constant. DAPI proved to be an excellent fluorescent probe for the investigation of the competitive binding of ionic liquids, surfactants, and biologically important compounds to CB7. The equilibrium constant of l-alkyl-3-methylimidazolium inclusion was found to go through a maximum as the aliphatic chain length was increased, reaching the highest value for the hexyl derivative. The variation of the anion had a small effect. Among cationic surfactants containing a dodecyl tail, the stability of CB7 complex diminished with the growing hydrophobicity of the head group.

Original languageEnglish
Pages (from-to)1645-1651
Number of pages7
JournalJournal of Physical Chemistry B
Volume113
Issue number6
DOIs
Publication statusPublished - Feb 12 2009

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Ionic Liquids
organic compounds
Fluorescent Dyes
Ionic liquids
Organic compounds
Fluorescence
surfactants
inclusions
fluorescence
probes
Cationic surfactants
Equilibrium constants
Hydrophobicity
hydrophobicity
liquids
Chain length
Encapsulation
Surface-Active Agents
Anions
Surface active agents

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Materials Chemistry
  • Surfaces, Coatings and Films

Cite this

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title = "Inclusion complex formation of ionic liquids and other cationic organic compounds with cucurbit[7]uril studied by 4',6-diamidino-2-phenylindole fluorescent probe",
abstract = "The encapsulation of 4',6-diamidino-2-phenylindole (DAPI) in the cucurbit[7]uril (CB7) cavity was studied by absorption, fluorescence, and NMR spectroscopic methods in aqueous solution. The profound change in the fluorescence characteristics was attributed to the formation of a very stable 1:1 inclusion complex. Three independent methods provided (1.1 ±0.1) x 107 M-1 value for the binding constant. DAPI proved to be an excellent fluorescent probe for the investigation of the competitive binding of ionic liquids, surfactants, and biologically important compounds to CB7. The equilibrium constant of l-alkyl-3-methylimidazolium inclusion was found to go through a maximum as the aliphatic chain length was increased, reaching the highest value for the hexyl derivative. The variation of the anion had a small effect. Among cationic surfactants containing a dodecyl tail, the stability of CB7 complex diminished with the growing hydrophobicity of the head group.",
author = "Zsombor Miskolczy and L{\'a}szl{\'o} Bicz{\'o}k and M{\'o}nika Megyesi and Istv{\'a}n Jablonkai",
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T1 - Inclusion complex formation of ionic liquids and other cationic organic compounds with cucurbit[7]uril studied by 4',6-diamidino-2-phenylindole fluorescent probe

AU - Miskolczy, Zsombor

AU - Biczók, László

AU - Megyesi, Mónika

AU - Jablonkai, István

PY - 2009/2/12

Y1 - 2009/2/12

N2 - The encapsulation of 4',6-diamidino-2-phenylindole (DAPI) in the cucurbit[7]uril (CB7) cavity was studied by absorption, fluorescence, and NMR spectroscopic methods in aqueous solution. The profound change in the fluorescence characteristics was attributed to the formation of a very stable 1:1 inclusion complex. Three independent methods provided (1.1 ±0.1) x 107 M-1 value for the binding constant. DAPI proved to be an excellent fluorescent probe for the investigation of the competitive binding of ionic liquids, surfactants, and biologically important compounds to CB7. The equilibrium constant of l-alkyl-3-methylimidazolium inclusion was found to go through a maximum as the aliphatic chain length was increased, reaching the highest value for the hexyl derivative. The variation of the anion had a small effect. Among cationic surfactants containing a dodecyl tail, the stability of CB7 complex diminished with the growing hydrophobicity of the head group.

AB - The encapsulation of 4',6-diamidino-2-phenylindole (DAPI) in the cucurbit[7]uril (CB7) cavity was studied by absorption, fluorescence, and NMR spectroscopic methods in aqueous solution. The profound change in the fluorescence characteristics was attributed to the formation of a very stable 1:1 inclusion complex. Three independent methods provided (1.1 ±0.1) x 107 M-1 value for the binding constant. DAPI proved to be an excellent fluorescent probe for the investigation of the competitive binding of ionic liquids, surfactants, and biologically important compounds to CB7. The equilibrium constant of l-alkyl-3-methylimidazolium inclusion was found to go through a maximum as the aliphatic chain length was increased, reaching the highest value for the hexyl derivative. The variation of the anion had a small effect. Among cationic surfactants containing a dodecyl tail, the stability of CB7 complex diminished with the growing hydrophobicity of the head group.

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