Journal of Physical Chemistry A, volume 119, issue 52, pages 13025-13037
Supramolecular Dimerization and [2 + 2] Photocycloaddition Reactions of Crown Ether Styryl Dyes Containing a Tethered Ammonium Group: Structure-Property Relationships
Ushakov E.N.
1, 2
,
Vedernikov Artem I.
2
,
Lobova Natalia A
2
,
Dmitrieva Svetlana N
2
,
Moiseeva Anna A.
4
,
Howard Judith A.
5
,
Alfimov Michael V
2
,
Fomina Marina V.
2, 4
Publication type: Journal Article
Publication date: 2015-12-17
Journal:
Journal of Physical Chemistry A
Quartile SCImago
Q2
Quartile WOS
Q2
Impact factor: 2.9
ISSN: 10895639, 15205215
Physical and Theoretical Chemistry
Abstract
Molecular self-assembly is an effective strategy for controlling the [2 + 2] photocycloaddition reaction of olefins. The geometrical properties of supramolecular assemblies are proven to have a critical effect on the efficiency and selectivity of this photoreaction both in the solid state and in solution, but the role of other factors remains poorly understood. Convenient supramolecular systems to study the structure-property relationships are pseudocyclic dimers spontaneously formed by styryl dyes containing a crown ether moiety and a remote ammonium group. New dyes of this type were synthesized to investigate the effects of structural and electronic factors on the quantitative characteristics of supramolecular dimerization and [2 + 2] photocycloaddition in solution. Variable structural parameters for the styryl dyes were the size and structure of macrocyclic moiety, the nature of heteroaromatic residue, and the length of the ammonioalkyl group attached to this residue. Quantum chemical calculations of the pseudocyclic dimers were performed in order to interpret the relationships between the structure of the ammonium dyes and the efficiency of the supramolecular photoreaction. One of the dimeric complexes was obtained in the crystalline state and studied by X-ray diffraction. The results obtained demonstrate that the photocycloaddition in the pseudocyclic dimers can be dramatically affected by the electronic structure of the styryl moieties, as dependent on the electron-donating ability of the substituents on the benzene ring, and by the conformational flexibility of the pseudocycle, which determines the mobility of the olefinic bonds. The significance of electronic factors is highlighted by the fact that the photocycloaddition quantum yield in geometrically similar dimeric structures varies from ≤10(-4) to 0.38. The latter value is unusually high for olefins in solution.
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Citations by publishers
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5 publications, 29.41%
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4 publications, 23.53%
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Springer Nature
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Wiley
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1 publication, 5.88%
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Royal Society of Chemistry (RSC)
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Royal Society of Chemistry (RSC)
1 publication, 5.88%
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1
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4
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- We do not take into account publications that without a DOI.
- Statistics recalculated only for publications connected to researchers, organizations and labs registered on the platform.
- Statistics recalculated weekly.
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Ushakov E. et al. Supramolecular Dimerization and [2 + 2] Photocycloaddition Reactions of Crown Ether Styryl Dyes Containing a Tethered Ammonium Group: Structure-Property Relationships // Journal of Physical Chemistry A. 2015. Vol. 119. No. 52. pp. 13025-13037.
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Ushakov E., Vedernikov A. I., Lobova N. A., Dmitrieva S. N., Kuz'mina L. G., Moiseeva A. A., Howard J. A., Alfimov M. V., Fomina M. V. Supramolecular Dimerization and [2 + 2] Photocycloaddition Reactions of Crown Ether Styryl Dyes Containing a Tethered Ammonium Group: Structure-Property Relationships // Journal of Physical Chemistry A. 2015. Vol. 119. No. 52. pp. 13025-13037.
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TY - JOUR
DO - 10.1021/acs.jpca.5b10758
UR - https://doi.org/10.1021%2Facs.jpca.5b10758
TI - Supramolecular Dimerization and [2 + 2] Photocycloaddition Reactions of Crown Ether Styryl Dyes Containing a Tethered Ammonium Group: Structure-Property Relationships
T2 - Journal of Physical Chemistry A
AU - Vedernikov, Artem I.
AU - Lobova, Natalia A
AU - Dmitrieva, Svetlana N
AU - Kuz'mina, Lyudmila G.
AU - Alfimov, Michael V
AU - Ushakov, E.N.
AU - Moiseeva, Anna A.
AU - Howard, Judith A.
AU - Fomina, Marina V.
PY - 2015
DA - 2015/12/17 00:00:00
PB - American Chemical Society (ACS)
SP - 13025-13037
IS - 52
VL - 119
SN - 1089-5639
SN - 1520-5215
ER -
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@article{2015_Ushakov,
author = {Artem I. Vedernikov and Natalia A Lobova and Svetlana N Dmitrieva and Lyudmila G. Kuz'mina and Michael V Alfimov and E.N. Ushakov and Anna A. Moiseeva and Judith A. Howard and Marina V. Fomina},
title = {Supramolecular Dimerization and [2 + 2] Photocycloaddition Reactions of Crown Ether Styryl Dyes Containing a Tethered Ammonium Group: Structure-Property Relationships},
journal = {Journal of Physical Chemistry A},
year = {2015},
volume = {119},
publisher = {American Chemical Society (ACS)},
month = {dec},
url = {https://doi.org/10.1021%2Facs.jpca.5b10758},
number = {52},
pages = {13025--13037},
doi = {10.1021/acs.jpca.5b10758}
}
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MLA
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Ushakov, E.N., et al. “Supramolecular Dimerization and [2 + 2] Photocycloaddition Reactions of Crown Ether Styryl Dyes Containing a Tethered Ammonium Group: Structure-Property Relationships.” Journal of Physical Chemistry A, vol. 119, no. 52, Dec. 2015, pp. 13025-13037. https://doi.org/10.1021%2Facs.jpca.5b10758.
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