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
Artem I. Vedernikov
1
,
E.N. Ushakov
2
,
Evgeny N Ushakov
2
,
Asya A Efremova
1
,
Anna A. Moiseeva
4
,
Natalia A Lobova
1
,
Yuri A. Strelenko
5
,
Michael V Alfimov
1
,
Judith A. Howard
6
,
Judith A. K. Howard
6
,
Marina V. Fomina
1
,
Publication type: Journal Article
Publication date: 2011-07-22
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
21744795
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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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., Ushakov E. N., 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., Howard J. A. K., Fomina M. V., Gromov S. P. 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://pubs.acs.org/doi/10.1021/jo201172w
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 - Ushakov, E.N.
AU - Ushakov, Evgeny N
AU - Efremova, Asya A
AU - Kuz'mina, Lyudmila G.
AU - Moiseeva, Anna A.
AU - Lobova, Natalia A
AU - Churakov, Andrei V.
AU - Strelenko, Yuri A.
AU - Alfimov, Michael V
AU - Howard, Judith A.
AU - Howard, Judith A. K.
AU - Fomina, Marina V.
AU - Gromov, Sergey P
PY - 2011
DA - 2011/07/22
PB - American Chemical Society (ACS)
SP - 6768-6779
IS - 16
VL - 76
PMID - 21744795
SN - 0022-3263
SN - 1520-6904
ER -
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@article{2011_Vedernikov,
author = {Artem I. Vedernikov and E.N. Ushakov and Evgeny N Ushakov and Asya A Efremova and Lyudmila G. Kuz'mina and Anna A. Moiseeva and Natalia A Lobova and Andrei V. Churakov and Yuri A. Strelenko and Michael V Alfimov and Judith A. Howard and Judith A. K. Howard and Marina V. Fomina and Sergey P Gromov},
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://pubs.acs.org/doi/10.1021/jo201172w},
number = {16},
pages = {6768--6779},
doi = {10.1021/jo201172w}
}
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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://pubs.acs.org/doi/10.1021/jo201172w.