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

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

Research output: Contribution to journalArticle

62 Citations (Scopus)

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

Fingerprint

Anions
Negative ions
Acetonitrile
Association reactions
Oxidation
Photooxidation
Water
Iodides
Chloroform
Chlorine compounds
Hydrogen peroxide
Titanium dioxide
Hydrogen Peroxide
Nuclear magnetic resonance spectroscopy
Methanol
bambus(6)uril
Salts
Crystal structure
Ions
acetonitrile

Keywords

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

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Svec, J., Dusek, M., Fejfarova, K., Stacko, P., Klán, P., Kaifer, A., ... 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

Anion-free bambus[6]uril and its supramolecular properties. / Svec, Jan; Dusek, Michal; Fejfarova, Karla; Stacko, Peter; Klán, Petr; Kaifer, Angel; Li, Wei; Hudeckova, Edita; Sindelar, Vladimir.

In: Chemistry - A European Journal, Vol. 17, No. 20, 09.05.2011, p. 5605-5612.

Research output: Contribution to journalArticle

Svec, J, Dusek, M, Fejfarova, K, Stacko, P, Klán, P, Kaifer, A, Li, W, Hudeckova, E & Sindelar, V 2011, 'Anion-free bambus[6]uril and its supramolecular properties', Chemistry - A European Journal, vol. 17, no. 20, pp. 5605-5612. https://doi.org/10.1002/chem.201003683
Svec, Jan ; Dusek, Michal ; Fejfarova, Karla ; Stacko, Peter ; Klán, Petr ; Kaifer, Angel ; Li, Wei ; Hudeckova, Edita ; Sindelar, Vladimir. / Anion-free bambus[6]uril and its supramolecular properties. In: Chemistry - A European Journal. 2011 ; Vol. 17, No. 20. pp. 5605-5612.
@article{26ea588f87454d63bb3ebf664b8c51a5,
title = "Anion-free bambus[6]uril and its supramolecular properties",
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.",
keywords = "anion receptors, halides, host-guest systems, macrocycles, supramolecular chemistry",
author = "Jan Svec and Michal Dusek and Karla Fejfarova and Peter Stacko and Petr Kl{\'a}n and Angel Kaifer and Wei Li and Edita Hudeckova and Vladimir Sindelar",
year = "2011",
month = "5",
day = "9",
doi = "10.1002/chem.201003683",
language = "English",
volume = "17",
pages = "5605--5612",
journal = "Chemistry - A European Journal",
issn = "0947-6539",
publisher = "Wiley-VCH Verlag",
number = "20",

}

TY - JOUR

T1 - Anion-free bambus[6]uril and its supramolecular properties

AU - Svec, Jan

AU - Dusek, Michal

AU - Fejfarova, Karla

AU - Stacko, Peter

AU - Klán, Petr

AU - Kaifer, Angel

AU - Li, Wei

AU - Hudeckova, Edita

AU - Sindelar, Vladimir

PY - 2011/5/9

Y1 - 2011/5/9

N2 - 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.

AB - 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.

KW - anion receptors

KW - halides

KW - host-guest systems

KW - macrocycles

KW - supramolecular chemistry

UR - http://www.scopus.com/inward/record.url?scp=79955608906&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=79955608906&partnerID=8YFLogxK

U2 - 10.1002/chem.201003683

DO - 10.1002/chem.201003683

M3 - Article

VL - 17

SP - 5605

EP - 5612

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

SN - 0947-6539

IS - 20

ER -