Russian Chemical Bulletin, volume 65, issue 7, pages 1761-1772
Synthesis, structure, electrochemistry, and photophysics of 2,5-dibenzylidenecyclopentanones containing in benzene rings substituents different in polarity
Vatsadze S. Z.
1
,
Gavrilova G V
1
,
Zyuzkevich F S
2
,
Nuriev V N
1
,
Krutko D P
1
,
Moiseeva A A
1
,
Shumyantsev A V
1
,
Vedernikov A.I.
2
,
Churakov A.V.
3
,
Kuz'mina L. G.
3
,
Howard J. A. K.
4
,
Gromov S P
1, 2
Publication type: Journal Article
Publication date: 2016-07-01
Journal:
Russian Chemical Bulletin
Quartile SCImago
Q3
Quartile WOS
Q3
Impact factor: 1.7
ISSN: 10665285, 15739171
General Chemistry
Abstract
A series of cross-conjugated dienones was synthesized to study the dependence of physicochemical characteristics on the nature of substituents in the aromatic groups of symmetric cyclopentanone dibenzylidene derivatives. The structure of compounds was established by electronic, IR, and NMR spectroscopy and X-ray diffraction study. All the compounds obtained possess the E,E-geometry. In the crystalline state, the arrangement of the dienone molecules is unfavorable for the intermolecular [2+2] photocycloaddition to take place. The low-temperature phases transition for unsubstituted diphenyl derivative of cyclopentanone was detected using variable-temperature X-ray diffraction and differential scanning calorimetry. Oxidation and reduction potentials of the dienones were measured by cyclic voltammetry. Their dependence on the nature and placement of substituents in the benzene rings was demonstrated. A linear correlation (R = 0.9343) between the difference of electrochemical oxidation and reduction potentials and the energy of the long-wavelength absorption maximum was found, that allows us to recommend the use of the data obtained in the correlation analysis of other compounds of this class.
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- We do not take into account publications that without a DOI.
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Vatsadze S. Z. et al. Synthesis, structure, electrochemistry, and photophysics of 2,5-dibenzylidenecyclopentanones containing in benzene rings substituents different in polarity // Russian Chemical Bulletin. 2016. Vol. 65. No. 7. pp. 1761-1772.
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Vatsadze S. Z., Gavrilova G. V., Zyuzkevich F. S., Nuriev V. N., Krutko D. P., Moiseeva A. A., Shumyantsev A. V., Vedernikov A., Churakov A., Kuz'mina L. G., Howard J. A. K., Gromov S. P. Synthesis, structure, electrochemistry, and photophysics of 2,5-dibenzylidenecyclopentanones containing in benzene rings substituents different in polarity // Russian Chemical Bulletin. 2016. Vol. 65. No. 7. pp. 1761-1772.
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TY - JOUR
DO - 10.1007/s11172-016-1508-7
UR - https://doi.org/10.1007%2Fs11172-016-1508-7
TI - Synthesis, structure, electrochemistry, and photophysics of 2,5-dibenzylidenecyclopentanones containing in benzene rings substituents different in polarity
T2 - Russian Chemical Bulletin
AU - Vatsadze, S. Z.
AU - Gavrilova, G V
AU - Zyuzkevich, F S
AU - Nuriev, V N
AU - Krutko, D P
AU - Moiseeva, A A
AU - Shumyantsev, A V
AU - Vedernikov, A.I.
AU - Churakov, A.V.
AU - Kuz'mina, L. G.
AU - Howard, J. A. K.
AU - Gromov, S P
PY - 2016
DA - 2016/07/01 00:00:00
PB - Springer Nature
SP - 1761-1772
IS - 7
VL - 65
SN - 1066-5285
SN - 1573-9171
ER -
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@article{2016_Vatsadze,
author = {S. Z. Vatsadze and G V Gavrilova and F S Zyuzkevich and V N Nuriev and D P Krutko and A A Moiseeva and A V Shumyantsev and A.I. Vedernikov and A.V. Churakov and L. G. Kuz'mina and J. A. K. Howard and S P Gromov},
title = {Synthesis, structure, electrochemistry, and photophysics of 2,5-dibenzylidenecyclopentanones containing in benzene rings substituents different in polarity},
journal = {Russian Chemical Bulletin},
year = {2016},
volume = {65},
publisher = {Springer Nature},
month = {jul},
url = {https://doi.org/10.1007%2Fs11172-016-1508-7},
number = {7},
pages = {1761--1772},
doi = {10.1007/s11172-016-1508-7}
}
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MLA
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Vatsadze, S. Z., et al. “Synthesis, structure, electrochemistry, and photophysics of 2,5-dibenzylidenecyclopentanones containing in benzene rings substituents different in polarity.” Russian Chemical Bulletin, vol. 65, no. 7, Jul. 2016, pp. 1761-1772. https://doi.org/10.1007%2Fs11172-016-1508-7.