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ACS Omega, volume 5, issue 40, pages 25993-26004

Highly Stable Supramolecular Donor-Acceptor Complexes Involving a Bis(18-Crown-6)azobenzene as Weak Donor: Structure-Property Relationships

Ushakov E.N. 1, 2
Vedernikov Artem I. 2
Efremova Asya A 2
Dmitrieva Svetlana N 2
Howard Judith A. 5
Publication typeJournal Article
Publication date2020-09-29
Journal: ACS Omega
Quartile SCImago
Q1
Quartile WOS
Q2
Impact factor4.1
ISSN24701343
General Chemistry
General Chemical Engineering
Abstract
The physicochemical properties of highly stable supramolecular donor–acceptor (D–A) complexes of a bis(18-crown-6)azobenzene (weak π-donor) with a series of bis(ammonioalkyl) derivatives of viologen-like molecules (π-acceptors) in acetonitrile were studied using cyclic voltammetry, UV–vis absorption spectroscopy, 1H NMR spectroscopy, and density functional theory (DFT) calculations. The crystalline structures of the bis(crown)azobenzene and its complex with a bis(ammoniopropyl) derivative of 2,7-diazapyrene were determined by X-ray diffraction analysis. In solution, all of the supramolecular D–A complexes studied have a pseudocyclic structure owing to ditopic coordination of the ammonium groups of the acceptor to the crown ether moieties of the donor. These complexes show somewhat lower stability as compared with the previously studied complexes of the related derivative of stilbene (strong π-donor), which is explained by the relatively weak intermolecular charge-transfer (CT) interactions. Time-dependent DFT calculations predict that the low-energy CT transition in the D–A complex of the bis(crown)azobenzene with a bis(ammoniopropyl) derivative of 4,4′-bipyridine lies between the local ππ* and nπ* transitions of the azobenzene. The absorption band associated with the CT transition is indiscernible in the spectrum since it is overlapped with broad and more intense ππ* and nπ* bands. It was found that the E → Z photoisomerization quantum yield of the bis(crown)azobenzene decreases by almost an order of magnitude upon the complexation with the 4,4′-bipyridine derivative. This effect was tentatively attributed to the intermolecular electron transfer that occurs in the 1ππ* excited state of the azobenzene and competes with the 1ππ* → 1nπ* internal conversion.

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Ushakov E. et al. Highly Stable Supramolecular Donor-Acceptor Complexes Involving a Bis(18-Crown-6)azobenzene as Weak Donor: Structure-Property Relationships // ACS Omega. 2020. Vol. 5. No. 40. pp. 25993-26004.
GOST all authors (up to 50) Copy
Ushakov E., Martyanov T. P., Vedernikov A. I., Efremova A. A., Moiseeva A. A., Kuz'mina L. G., Dmitrieva S. N., Howard J. A., Fomina M. V. Highly Stable Supramolecular Donor-Acceptor Complexes Involving a Bis(18-Crown-6)azobenzene as Weak Donor: Structure-Property Relationships // ACS Omega. 2020. Vol. 5. No. 40. pp. 25993-26004.
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TY - JOUR
DO - 10.1021/acsomega.0c03441
UR - https://doi.org/10.1021%2Facsomega.0c03441
TI - Highly Stable Supramolecular Donor-Acceptor Complexes Involving a Bis(18-Crown-6)azobenzene as Weak Donor: Structure-Property Relationships
T2 - ACS Omega
AU - Vedernikov, Artem I.
AU - Efremova, Asya A
AU - Kuz'mina, Lyudmila G.
AU - Dmitrieva, Svetlana N
AU - Ushakov, E.N.
AU - Martyanov, Timofey P
AU - Moiseeva, Anna A.
AU - Howard, Judith A.
AU - Fomina, Marina V.
PY - 2020
DA - 2020/09/29 00:00:00
PB - American Chemical Society (ACS)
SP - 25993-26004
IS - 40
VL - 5
PMID - 33073126
SN - 2470-1343
ER -
BibTex |
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@article{2020_Ushakov
author = {Artem I. Vedernikov and Asya A Efremova and Lyudmila G. Kuz'mina and Svetlana N Dmitrieva and E.N. Ushakov and Timofey P Martyanov and Anna A. Moiseeva and Judith A. Howard and Marina V. Fomina},
title = {Highly Stable Supramolecular Donor-Acceptor Complexes Involving a Bis(18-Crown-6)azobenzene as Weak Donor: Structure-Property Relationships},
journal = {ACS Omega},
year = {2020},
volume = {5},
publisher = {American Chemical Society (ACS)},
month = {sep},
url = {https://doi.org/10.1021%2Facsomega.0c03441},
number = {40},
pages = {25993--26004},
doi = {10.1021/acsomega.0c03441}
}
MLA
Cite this
MLA Copy
Ushakov, E.N., et al. “Highly Stable Supramolecular Donor-Acceptor Complexes Involving a Bis(18-Crown-6)azobenzene as Weak Donor: Structure-Property Relationships.” ACS Omega, vol. 5, no. 40, Sep. 2020, pp. 25993-26004. https://doi.org/10.1021%2Facsomega.0c03441.
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