Journal of Physical Organic Chemistry
New dithiacrown-ether butadienyl dyes: Synthesis, structure, and complex formation with heavy metal cations
Vedernikov Artem I.
1
,
Ushakov E.N.
2
,
Strelenko Yuri A.
4
,
Wörner Michael
5
,
Braun André
5
,
Howard Judith A.
6
,
Alfimov Michael V
1
,
Publication type: Journal Article
Publication date: 2009-09-18
Quartile SCImago
Q3
Quartile WOS
Q3
Impact factor: 1.8
ISSN: 08943230, 10991395
DOI:
10.1002/poc.1596
Organic Chemistry
Physical and Theoretical Chemistry
Abstract
Benzothiazole type butadienyl dyes containing a dithia-15-crown-5 (2a) or dithia-18-crown-6 ether (2b) moieties were synthesized. The structures of dyes 2a,b and their complexes with Ag R and Pb 2R were studied by an X-ray crystallography. It was found that the conformations of dithiacrown–ether moieties of dyes 2a,b are unfavorable for complex formation and change significantly upon binding of Ag R or Pb 2R . The complexation of 2a,b with Ag R , Cd 2R ,Pb 2R ,andHg 2R inwater–acetonitrilemixtureswithdifferentcontentsofwater(PW ¼0–75%,v/v) wasstudiedby 1 H NMR, UV–Vis spectroscopy, and polarography. In anhydrous acetonitrile, the stability constants of 1:1 complexes change in the sequence Cd 2R 10 4 ). The complexation of 2a,b with Hg 2R at PW £50% is accompanied by a substantial hypsochromic effect. This allows dithiacrown-containing butadienyl dyes to be used as selective optical molecular sensors for heavy metal ions, in particular, in aqueous solutions. Copyright 2009 John Wiley & Sons, Ltd. Supporting information may be found in the online version of this article.
Citations by journals
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1
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Advanced Functional Materials
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Advanced Functional Materials
1 publication, 50%
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1
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Citations by publishers
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1
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Wiley
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Wiley
1 publication, 50%
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1
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Vedernikov A. I. et al. New dithiacrown-ether butadienyl dyes: Synthesis, structure, and complex formation with heavy metal cations // Journal of Physical Organic Chemistry. 2009.
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Vedernikov A. I., Ushakov E., Kuz'mina L. G., Churakov A. V., Strelenko Y. A., Wörner M., Braun A., Howard J. A., Alfimov M. V., Fomina M. V. New dithiacrown-ether butadienyl dyes: Synthesis, structure, and complex formation with heavy metal cations // Journal of Physical Organic Chemistry. 2009.
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TY - JOUR
DO - 10.1002/poc.1596
UR - https://doi.org/10.1002%2Fpoc.1596
TI - New dithiacrown-ether butadienyl dyes: Synthesis, structure, and complex formation with heavy metal cations
T2 - Journal of Physical Organic Chemistry
AU - Vedernikov, Artem I.
AU - Kuz'mina, Lyudmila G.
AU - Strelenko, Yuri A.
AU - Wörner, Michael
AU - Alfimov, Michael V
AU - Ushakov, E.N.
AU - Churakov, Andrei V.
AU - Braun, André
AU - Howard, Judith A.
AU - Fomina, Marina V.
PY - 2009
DA - 2009/09/18 00:00:00
PB - Wiley
SN - 0894-3230
SN - 1099-1395
ER -
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@article{2009_Vedernikov,
author = {Artem I. Vedernikov and Lyudmila G. Kuz'mina and Yuri A. Strelenko and Michael Wörner and Michael V Alfimov and E.N. Ushakov and Andrei V. Churakov and André Braun and Judith A. Howard and Marina V. Fomina},
title = {New dithiacrown-ether butadienyl dyes: Synthesis, structure, and complex formation with heavy metal cations},
journal = {Journal of Physical Organic Chemistry},
year = {2009},
publisher = {Wiley},
month = {sep},
url = {https://doi.org/10.1002%2Fpoc.1596},
doi = {10.1002/poc.1596}
}