Synthesis, structure, and characterization of chromo(fluoro)ionophores with cation-triggered emission based on N-methylaza-crown-ether styryl dyes
Marina V. Fomina
1
,
Sergey P Gromov
2
,
Svetlana N Dmitrieva
1, 2
,
Artem I. Vedernikov
1, 2
,
Nikolay A Kurchavov
1, 2
,
Lyudmila G. Kuz'mina
3, 4
,
Sergey K Sazonov
1, 2
,
Yuri A. Strelenko
5, 6
,
Michael V Alfimov
1, 2
,
Judith A. Howard
7
,
Judith A. K. Howard
8
,
E.N. Ushakov
9
,
Evgeny N Ushakov
10
Publication type: Journal Article
Publication date: 2013-09-12
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
24001286
Organic Chemistry
Abstract
Novel 2-benzothiazole-, 4-pyridine-, and 2- and 4-quinoline-based styryl dyes containing an N-methylbenzoaza-15(18)-crown-5(6)-ether moiety were synthesized. A detailed electronic spectroscopy study revealed high performance of these compounds as optical molecular sensors for alkali and alkaline-earth metal cations. They were shown to considerably surpass analogous chromoionophores based on N-phenylaza-crown ethers regarding both the ionochromism and the cation-binding ability. In addition, they act as fluorescent sensors for the metal cations by demonstrating cation-triggered emission. Upon complexation with Ba(2+), the fluorescence enhancement factor reaches 61. The structural features of dyes and their metal complexes were studied by NMR spectroscopy and X-ray diffraction. The high degree of macrocycle preorganization was found to be one of the factors determining the high cation-binding ability of the sensor molecules based on N-methylbenzoaza-crown ethers.
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Total citations:
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GOST
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Fomina M. V. et al. Synthesis, structure, and characterization of chromo(fluoro)ionophores with cation-triggered emission based on N-methylaza-crown-ether styryl dyes // Journal of Organic Chemistry. 2013. Vol. 78. No. 19. pp. 9834-9847.
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Fomina M. V., Gromov S. P., Dmitrieva S. N., Vedernikov A. I., Kurchavov N. A., Kuz'mina L. G., Sazonov S. K., Strelenko Y. A., Alfimov M. V., Howard J. A., Howard J. A. K., Ushakov E., Ushakov E. N. Synthesis, structure, and characterization of chromo(fluoro)ionophores with cation-triggered emission based on N-methylaza-crown-ether styryl dyes // Journal of Organic Chemistry. 2013. Vol. 78. No. 19. pp. 9834-9847.
Cite this
RIS
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TY - JOUR
DO - 10.1021/jo401555a
UR - https://pubs.acs.org/doi/10.1021/jo401555a
TI - Synthesis, structure, and characterization of chromo(fluoro)ionophores with cation-triggered emission based on N-methylaza-crown-ether styryl dyes
T2 - Journal of Organic Chemistry
AU - Fomina, Marina V.
AU - Gromov, Sergey P
AU - Dmitrieva, Svetlana N
AU - Vedernikov, Artem I.
AU - Kurchavov, Nikolay A
AU - Kuz'mina, Lyudmila G.
AU - Sazonov, Sergey K
AU - Strelenko, Yuri A.
AU - Alfimov, Michael V
AU - Howard, Judith A.
AU - Howard, Judith A. K.
AU - Ushakov, E.N.
AU - Ushakov, Evgeny N
PY - 2013
DA - 2013/09/12
PB - American Chemical Society (ACS)
SP - 9834-9847
IS - 19
VL - 78
PMID - 24001286
SN - 0022-3263
SN - 1520-6904
ER -
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BibTex (up to 50 authors)
Copy
@article{2013_Fomina,
author = {Marina V. Fomina and Sergey P Gromov and Svetlana N Dmitrieva and Artem I. Vedernikov and Nikolay A Kurchavov and Lyudmila G. Kuz'mina and Sergey K Sazonov and Yuri A. Strelenko and Michael V Alfimov and Judith A. Howard and Judith A. K. Howard and E.N. Ushakov and Evgeny N Ushakov},
title = {Synthesis, structure, and characterization of chromo(fluoro)ionophores with cation-triggered emission based on N-methylaza-crown-ether styryl dyes},
journal = {Journal of Organic Chemistry},
year = {2013},
volume = {78},
publisher = {American Chemical Society (ACS)},
month = {sep},
url = {https://pubs.acs.org/doi/10.1021/jo401555a},
number = {19},
pages = {9834--9847},
doi = {10.1021/jo401555a}
}
Cite this
MLA
Copy
Fomina, Marina V., et al. “Synthesis, structure, and characterization of chromo(fluoro)ionophores with cation-triggered emission based on N-methylaza-crown-ether styryl dyes.” Journal of Organic Chemistry, vol. 78, no. 19, Sep. 2013, pp. 9834-9847. https://pubs.acs.org/doi/10.1021/jo401555a.
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