Journal of Organic Chemistry, volume 76, issue 16, pages 6768-6779
Synthesis, structure, and properties of supramolecular charge-transfer complexes between bis(18-crown-6)stilbene and ammonioalkyl derivatives of 4,4′-bipyridine and 2,7-diazapyrene
Vedernikov Artem I.
1
,
Ushakov E.N.
2
,
Efremova Asya A
1
,
Moiseeva Anna A.
4
,
Lobova Natalia A
1
,
Strelenko Yuri A.
5
,
Alfimov Michael V
1
,
Howard Judith A.
6
,
Publication type: Journal Article
Publication date: 2011-07-22
Journal:
Journal of Organic Chemistry
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 3.6
ISSN: 00223263, 15206904
Organic Chemistry
Abstract
4,4'-Bipyridine and 2,7-diazapyrene derivatives (A) having two ammonioalkyl N-substituents were synthesized. The complex formation of these compounds with bis(18-crown-6)stilbene (D) was studied by spectrophotometry, cyclic voltammetry, (1)H NMR spectroscopy, and X-ray diffraction analysis. In MeCN, π-donor D and π-acceptors A form supramolecular 1:1 (D·A) and 2:1 (D·A·D) charge-transfer complexes. The D·A complexes have a pseudocyclic structure as a result of ditopic binding of the ammonium groups to the crown-ether fragments. The better the geometric matching between the components, the higher the stability of the D·A complexes (log K up to 9.39). A key driving force of the D·A·D complex formation is the excessive steric strain in the precursor D·A complexes. The pseudocyclic D·A complexes involving the ammoniopropyl derivative of 4,4'-bipyridine were obtained as single crystals. Crystallization of the related ammonioethyl derivative was accompanied by transition of the D·A complexes to a structure of the (D·A)(m) coordination polymer type.
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- We do not take into account publications that without a DOI.
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Vedernikov A. I. et al. Synthesis, structure, and properties of supramolecular charge-transfer complexes between bis(18-crown-6)stilbene and ammonioalkyl derivatives of 4,4′-bipyridine and 2,7-diazapyrene // Journal of Organic Chemistry. 2011. Vol. 76. No. 16. pp. 6768-6779.
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Vedernikov A. I., Ushakov E., Efremova A. A., Kuz'mina L. G., Moiseeva A. A., Lobova N. A., Churakov A. V., Strelenko Y. A., Alfimov M. V., Howard J. A., Fomina M. V. Synthesis, structure, and properties of supramolecular charge-transfer complexes between bis(18-crown-6)stilbene and ammonioalkyl derivatives of 4,4′-bipyridine and 2,7-diazapyrene // Journal of Organic Chemistry. 2011. Vol. 76. No. 16. pp. 6768-6779.
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TY - JOUR
DO - 10.1021/jo201172w
UR - https://doi.org/10.1021%2Fjo201172w
TI - Synthesis, structure, and properties of supramolecular charge-transfer complexes between bis(18-crown-6)stilbene and ammonioalkyl derivatives of 4,4′-bipyridine and 2,7-diazapyrene
T2 - Journal of Organic Chemistry
AU - Vedernikov, Artem I.
AU - Efremova, Asya A
AU - Kuz'mina, Lyudmila G.
AU - Lobova, Natalia A
AU - Strelenko, Yuri A.
AU - Alfimov, Michael V
AU - Ushakov, E.N.
AU - Moiseeva, Anna A.
AU - Churakov, Andrei V.
AU - Howard, Judith A.
AU - Fomina, Marina V.
PY - 2011
DA - 2011/07/22 00:00:00
PB - American Chemical Society (ACS)
SP - 6768-6779
IS - 16
VL - 76
SN - 0022-3263
SN - 1520-6904
ER -
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@article{2011_Vedernikov,
author = {Artem I. Vedernikov and Asya A Efremova and Lyudmila G. Kuz'mina and Natalia A Lobova and Yuri A. Strelenko and Michael V Alfimov and E.N. Ushakov and Anna A. Moiseeva and Andrei V. Churakov and Judith A. Howard and Marina V. Fomina},
title = {Synthesis, structure, and properties of supramolecular charge-transfer complexes between bis(18-crown-6)stilbene and ammonioalkyl derivatives of 4,4′-bipyridine and 2,7-diazapyrene},
journal = {Journal of Organic Chemistry},
year = {2011},
volume = {76},
publisher = {American Chemical Society (ACS)},
month = {jul},
url = {https://doi.org/10.1021%2Fjo201172w},
number = {16},
pages = {6768--6779},
doi = {10.1021/jo201172w}
}
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MLA
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Vedernikov, Artem I., et al. “Synthesis, structure, and properties of supramolecular charge-transfer complexes between bis(18-crown-6)stilbene and ammonioalkyl derivatives of 4,4′-bipyridine and 2,7-diazapyrene.” Journal of Organic Chemistry, vol. 76, no. 16, Jul. 2011, pp. 6768-6779. https://doi.org/10.1021%2Fjo201172w.