Journal of Photochemistry and Photobiology A: Chemistry, volume 340, pages 80-87

Self-assembly through hydrogen bonding and photochemical properties of supramolecular complexes of bis(18-crown-6)stilbene with alkanediammonium ions

Publication typeJournal Article
Publication date2017-05-01
Quartile SCImago
Q2
Quartile WOS
Q2
Impact factor4.3
ISSN10106030, 18732666
General Chemistry
General Chemical Engineering
General Physics and Astronomy
Abstract
Abstract Binding of alkanediammonium ions +H3N(CH2)nNH3+, n = 2–6, to (E)-bis(18-crown-6)stilbene initiates the [2 + 2] photocycloaddition reaction leading mainly to the rctt isomer of 1,2,3,4-tetrakis(benzo-18-crown-6)cyclobutane. The high efficiency and stereoselectivity of this photoreaction in dilute solution are due to the formation of bis-pseudosandwich complexes consisting of two stilbene molecules and two alkanediammonium ions. With a decrease in the length of the polymethylene spacers in the 2:2 complex, the quantum yield of supramolecular [2 + 2] photocycloaddition increases from 0.02 to 0.27, while the quantum yield of the competing E–Z photoisomerization decreases from 0.12 to 0.06. Spectrophotometric observations and density functional theory calculations revealed that (Z)-bis(18-crown-6)stilbene, unlike the E isomer, is able to form pseudocyclic 1:1 complexes with +H3N(CH2)nNH3+, n = 2–6, owing to the proximity of two crown ether moieties. The peculiar spectral properties of these complexes are associated with large torsion angles around the ethylene–benzocrown single bonds. X-ray diffraction analysis showed that co-crystallization of (E)-bis(18-crown-6)stilbene with 1,6-hexanediammonium diperchlorate affords a linear polymer in which the alternating stilbene molecules and diammonium ions are connected by hydrogen bonds.

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Ushakov E. et al. Self-assembly through hydrogen bonding and photochemical properties of supramolecular complexes of bis(18-crown-6)stilbene with alkanediammonium ions // Journal of Photochemistry and Photobiology A: Chemistry. 2017. Vol. 340. pp. 80-87.
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Ushakov E., Martyanov T. P., Vedernikov A. I., Pikalov O. V., Efremova A. A., Kuz'mina L. G., Howard J. A., Alfimov M. V., Fomina M. V. Self-assembly through hydrogen bonding and photochemical properties of supramolecular complexes of bis(18-crown-6)stilbene with alkanediammonium ions // Journal of Photochemistry and Photobiology A: Chemistry. 2017. Vol. 340. pp. 80-87.
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TY - JOUR
DO - 10.1016/j.jphotochem.2017.03.003
UR - https://doi.org/10.1016%2Fj.jphotochem.2017.03.003
TI - Self-assembly through hydrogen bonding and photochemical properties of supramolecular complexes of bis(18-crown-6)stilbene with alkanediammonium ions
T2 - Journal of Photochemistry and Photobiology A: Chemistry
AU - Martyanov, Timofey P
AU - Vedernikov, Artem I.
AU - Pikalov, Oleg V
AU - Efremova, Asya A
AU - Kuz'mina, Lyudmila G.
AU - Alfimov, Michael V
AU - Ushakov, E.N.
AU - Howard, Judith A.
AU - Fomina, Marina V.
PY - 2017
DA - 2017/05/01 00:00:00
PB - Elsevier
SP - 80-87
VL - 340
SN - 1010-6030
SN - 1873-2666
ER -
BibTex
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@article{2017_Ushakov
author = {Timofey P Martyanov and Artem I. Vedernikov and Oleg V Pikalov and Asya A Efremova and Lyudmila G. Kuz'mina and Michael V Alfimov and E.N. Ushakov and Judith A. Howard and Marina V. Fomina},
title = {Self-assembly through hydrogen bonding and photochemical properties of supramolecular complexes of bis(18-crown-6)stilbene with alkanediammonium ions},
journal = {Journal of Photochemistry and Photobiology A: Chemistry},
year = {2017},
volume = {340},
publisher = {Elsevier},
month = {may},
url = {https://doi.org/10.1016%2Fj.jphotochem.2017.03.003},
pages = {80--87},
doi = {10.1016/j.jphotochem.2017.03.003}
}
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