Journal of Organic Chemistry, volume 86, issue 4, pages 3164-3175
Pseudodimeric Complexes of an (18-Crown-6)stilbene with Styryl Dyes Containing an Ammonioalkyl Group: Synthesis, Structure, and Stereospecific [2 + 2] Cross-Photocycloaddition
Ushakov E.N.
1, 2
,
Nuriev Vyacheslav N
2, 3
,
Aleksandrova Nadezhda A
2
,
Sazonov Sergey K
2
,
Vedernikov Artem I.
2
,
Klimenko Lubov S
5
,
Martyanova Elena G
1
,
Fomina Marina V.
2, 3
2
Publication type: Journal Article
Publication date: 2021-02-02
Journal:
Journal of Organic Chemistry
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 3.6
ISSN: 00223263, 15206904
Organic Chemistry
Abstract
A new efficient method was proposed for the synthesis of (18-crown-6)stilbene; the structure of the product was confirmed by X-ray diffraction analysis. In MeCN, this compound forms pseudodimeric complexes with N-(2-ammonioethyl)-4-styrylpyridinium and N-(3-ammoniopropyl)-4-styrylpyridinium diperchlorates via hydrogen bonding between the ammonium group and the crown ether oxygen atoms. The ammonioethyl derivative was synthesized for the first time. The stability constants and spectral characteristics of the complexes were measured by spectrophotometric and fluorescence titration. Photoirradiation of the pseudodimeric complex of (18-crown-6)stilbene with the ammoniopropyl dye resulted in the stereospecific [2 + 2] cross-photocycloaddition reaction. The replacement of the stilbene moiety in the crown compound by a styrylpyridine moiety led to a 5-fold increase in the quantum yield of the photoprocess. The most probable cause for this effect is the presence of photoinduced electron transfer in (18-crown-6)stilbene complexes. This assumption is confirmed by fluorescence lifetime spectroscopy and density functional theory calculations.
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ACS Omega
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ACS Omega
1 publication, 12.5%
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Communications Chemistry
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1 publication, 12.5%
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Russian Chemical Bulletin
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1 publication, 12.5%
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Organic and Biomolecular Chemistry
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1 publication, 12.5%
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1
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Citations by publishers
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1
2
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Springer Nature
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Springer Nature
2 publications, 25%
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American Chemical Society (ACS)
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American Chemical Society (ACS)
1 publication, 12.5%
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Elsevier
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Elsevier
1 publication, 12.5%
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Wiley
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Wiley
1 publication, 12.5%
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Royal Society of Chemistry (RSC)
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Royal Society of Chemistry (RSC)
1 publication, 12.5%
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1
2
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Martyanov T. P. et al. Pseudodimeric Complexes of an (18-Crown-6)stilbene with Styryl Dyes Containing an Ammonioalkyl Group: Synthesis, Structure, and Stereospecific [2 + 2] Cross-Photocycloaddition // Journal of Organic Chemistry. 2021. Vol. 86. No. 4. pp. 3164-3175.
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Martyanov T. P., Ushakov E., Nuriev V. N., Aleksandrova N. A., Sazonov S. K., Vedernikov A. I., Kuz'mina L. G., Klimenko L. S., Martyanova E. G., Fomina M. V. Pseudodimeric Complexes of an (18-Crown-6)stilbene with Styryl Dyes Containing an Ammonioalkyl Group: Synthesis, Structure, and Stereospecific [2 + 2] Cross-Photocycloaddition // Journal of Organic Chemistry. 2021. Vol. 86. No. 4. pp. 3164-3175.
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TY - JOUR
DO - 10.1021/acs.joc.0c02514
UR - https://doi.org/10.1021%2Facs.joc.0c02514
TI - Pseudodimeric Complexes of an (18-Crown-6)stilbene with Styryl Dyes Containing an Ammonioalkyl Group: Synthesis, Structure, and Stereospecific [2 + 2] Cross-Photocycloaddition
T2 - Journal of Organic Chemistry
AU - Nuriev, Vyacheslav N
AU - Aleksandrova, Nadezhda A
AU - Sazonov, Sergey K
AU - Vedernikov, Artem I.
AU - Kuz'mina, Lyudmila G.
AU - Klimenko, Lubov S
AU - Martyanova, Elena G
AU - Martyanov, Timofey P
AU - Ushakov, E.N.
AU - Fomina, Marina V.
PY - 2021
DA - 2021/02/02 00:00:00
PB - American Chemical Society (ACS)
SP - 3164-3175
IS - 4
VL - 86
SN - 0022-3263
SN - 1520-6904
ER -
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@article{2021_Martyanov,
author = {Vyacheslav N Nuriev and Nadezhda A Aleksandrova and Sergey K Sazonov and Artem I. Vedernikov and Lyudmila G. Kuz'mina and Lubov S Klimenko and Elena G Martyanova and Timofey P Martyanov and E.N. Ushakov and Marina V. Fomina},
title = {Pseudodimeric Complexes of an (18-Crown-6)stilbene with Styryl Dyes Containing an Ammonioalkyl Group: Synthesis, Structure, and Stereospecific [2 + 2] Cross-Photocycloaddition},
journal = {Journal of Organic Chemistry},
year = {2021},
volume = {86},
publisher = {American Chemical Society (ACS)},
month = {feb},
url = {https://doi.org/10.1021%2Facs.joc.0c02514},
number = {4},
pages = {3164--3175},
doi = {10.1021/acs.joc.0c02514}
}
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Martyanov, Timofey P., et al. “Pseudodimeric Complexes of an (18-Crown-6)stilbene with Styryl Dyes Containing an Ammonioalkyl Group: Synthesis, Structure, and Stereospecific [2 + 2] Cross-Photocycloaddition.” Journal of Organic Chemistry, vol. 86, no. 4, Feb. 2021, pp. 3164-3175. https://doi.org/10.1021%2Facs.joc.0c02514.