Stereospecific [2 + 2]-cross-photocycloaddition in a supramolecular donor–acceptor complex
E.N. Ushakov
1
,
Artem I. Vedernikov
1
,
Sergey K Sazonov
1
,
Igor G Strelnikov
1
,
Lubov S Klimenko
2
,
Michael V Alfimov
1
,
Marina V. Fomina
1, 3
1
Publication type: Journal Article
Publication date: 2019-01-01
scimago Q3
wos Q3
SJR: 0.334
CiteScore: 3.2
Impact factor: 1.5
ISSN: 00404039, 18733581
Organic Chemistry
Drug Discovery
Biochemistry
Abstract
Abstract A bis(propylammonium) derivative of (E)-4-(4-mercaptostyryl)pyridine, which was synthesized for the first time, forms a highly stable bimolecular complex with a bis(18-crown-6 ether) derivative of (E)-stilbene in solution owing to ditopic coordination via hydrogen bonds. The complex formation results in much faster deactivation of the excited states of both compounds, which is explained by photoinduced electron transfer from the stilbene derivative to the styrylpyridinium dye. Despite this, the complexed olefins undergo [2 + 2]-cross-photocycloaddition upon selective excitation of the dye to afford solely the syn-cycloadduct. The retro-photocycloaddition occurs readily upon UV irradiation of the cycloadduct and leads to the initial bimolecular complex.
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Total citations:
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Citations from 2024:
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(11%)
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Ushakov E. et al. Stereospecific [2 + 2]-cross-photocycloaddition in a supramolecular donor–acceptor complex // Tetrahedron Letters. 2019. Vol. 60. No. 2. pp. 150-153.
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Ushakov E., Martyanov T. P., Vedernikov A. I., Sazonov S. K., Strelnikov I. G., Klimenko L. S., Alfimov M. V., Fomina M. V. Stereospecific [2 + 2]-cross-photocycloaddition in a supramolecular donor–acceptor complex // Tetrahedron Letters. 2019. Vol. 60. No. 2. pp. 150-153.
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RIS
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TY - JOUR
DO - 10.1016/j.tetlet.2018.11.077
UR - https://linkinghub.elsevier.com/retrieve/pii/S004040391831431X
TI - Stereospecific [2 + 2]-cross-photocycloaddition in a supramolecular donor–acceptor complex
T2 - Tetrahedron Letters
AU - Ushakov, E.N.
AU - Martyanov, Timofey P
AU - Vedernikov, Artem I.
AU - Sazonov, Sergey K
AU - Strelnikov, Igor G
AU - Klimenko, Lubov S
AU - Alfimov, Michael V
AU - Fomina, Marina V.
PY - 2019
DA - 2019/01/01
PB - Elsevier
SP - 150-153
IS - 2
VL - 60
SN - 0040-4039
SN - 1873-3581
ER -
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BibTex (up to 50 authors)
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@article{2019_Ushakov,
author = {E.N. Ushakov and Timofey P Martyanov and Artem I. Vedernikov and Sergey K Sazonov and Igor G Strelnikov and Lubov S Klimenko and Michael V Alfimov and Marina V. Fomina},
title = {Stereospecific [2 + 2]-cross-photocycloaddition in a supramolecular donor–acceptor complex},
journal = {Tetrahedron Letters},
year = {2019},
volume = {60},
publisher = {Elsevier},
month = {jan},
url = {https://linkinghub.elsevier.com/retrieve/pii/S004040391831431X},
number = {2},
pages = {150--153},
doi = {10.1016/j.tetlet.2018.11.077}
}
Cite this
MLA
Copy
Ushakov, E.N., et al. “Stereospecific [2 + 2]-cross-photocycloaddition in a supramolecular donor–acceptor complex.” Tetrahedron Letters, vol. 60, no. 2, Jan. 2019, pp. 150-153. https://linkinghub.elsevier.com/retrieve/pii/S004040391831431X.