New Journal of Chemistry, volume 31, issue 6, pages 980-994

4-Styrylquinolines: Synthesis and study of [2 + 2]-photocycloaddition reactions in thin films and single crystals

Publication typeJournal Article
Publication date2007-04-18
Quartile SCImago
Q2
Quartile WOS
Q2
Impact factor3.3
ISSN11440546, 13699261
Materials Chemistry
General Chemistry
Catalysis
Abstract
Four new (E)-4-styrylquinoline compounds containing two methoxy substituents or an 18-crown-6-ether fragment were synthesized in order to investigate the [2 + 2]-photocycloaddition (PCA) reaction in the solid state. These compounds reveal different abilities to undergo the photoreaction depending on the packing of the quinoline molecules in thin polycrystalline films and single crystals. The only products from the irradiation of (E)-4-styrylquinolines were an rctt isomer of 1,2,3,4-tetrasubstituted cyclobutane and, rarely, a Z isomer of the styrylquinoline. The rctt cyclobutane derivative was formed as a result of the PCA of centrosymmetric syn-‘head-to-tail’ dimeric pairs of the reactant species that are preorganized in such a way as to promote this reaction. Peculiarities in the crystal packing motifs that are typical for single crystals of 4-styrylquinoline compounds are discussed. The solvate molecules can affect significantly the packing of styrylquinolines. Benzene solvate molecules create a soft, flexible, shell about the dimeric pairs that facilitates the PCA in the single crystal without causing degradation of the crystal. In crystal packing that contains CH2Cl2 and H2O solvate molecules, they are prone to form complicated systems of hydrogen bonds with crown-ether oxygen atoms and each other. This results in distorting the organic molecule geometry toward non-planarity and accomplishing a new type of crystal packing uncommon for styrylheterocycles, in which the PCA is impossible. The topochemical single-crystal-to-single-crystal PCA reaction was monitored for one of the species. Two cyclobutane derivatives obtained in single crystals were subjected to recrystallization from a solution. The new single crystals formed belong to different crystal systems, with different unit cell parameters as compared with initial single crystals; significant differences in the geometry of the cyclobutane molecules were also found. This implies that the cyclobutane derivatives obtained in the solid phase have a molecular geometry that is somewhat stressed.

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Kuz'mina L. G. et al. 4-Styrylquinolines: Synthesis and study of [2 + 2]-photocycloaddition reactions in thin films and single crystals // New Journal of Chemistry. 2007. Vol. 31. No. 6. pp. 980-994.
GOST all authors (up to 50) Copy
Kuz'mina L. G., Vedernikov A. I., Lobova N. A., Churakov A. V., Howard J. A., Alfimov M. V., Fomina M. V. 4-Styrylquinolines: Synthesis and study of [2 + 2]-photocycloaddition reactions in thin films and single crystals // New Journal of Chemistry. 2007. Vol. 31. No. 6. pp. 980-994.
RIS |
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RIS Copy
TY - JOUR
DO - 10.1039/b615056j
UR - https://doi.org/10.1039%2Fb615056j
TI - 4-Styrylquinolines: Synthesis and study of [2 + 2]-photocycloaddition reactions in thin films and single crystals
T2 - New Journal of Chemistry
AU - Kuz'mina, Lyudmila G.
AU - Vedernikov, Artem I.
AU - Lobova, Natalia A
AU - Alfimov, Michael V
AU - Churakov, Andrei V.
AU - Howard, Judith A.
AU - Fomina, Marina V.
PY - 2007
DA - 2007/04/18 00:00:00
PB - Royal Society of Chemistry (RSC)
SP - 980-994
IS - 6
VL - 31
SN - 1144-0546
SN - 1369-9261
ER -
BibTex |
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BibTex Copy
@article{2007_Kuz'mina
author = {Lyudmila G. Kuz'mina and Artem I. Vedernikov and Natalia A Lobova and Michael V Alfimov and Andrei V. Churakov and Judith A. Howard and Marina V. Fomina},
title = {4-Styrylquinolines: Synthesis and study of [2 + 2]-photocycloaddition reactions in thin films and single crystals},
journal = {New Journal of Chemistry},
year = {2007},
volume = {31},
publisher = {Royal Society of Chemistry (RSC)},
month = {apr},
url = {https://doi.org/10.1039%2Fb615056j},
number = {6},
pages = {980--994},
doi = {10.1039/b615056j}
}
MLA
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MLA Copy
Kuz'mina, Lyudmila G., et al. “4-Styrylquinolines: Synthesis and study of [2 + 2]-photocycloaddition reactions in thin films and single crystals.” New Journal of Chemistry, vol. 31, no. 6, Apr. 2007, pp. 980-994. https://doi.org/10.1039%2Fb615056j.
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