Open Access
Push–Pull Derivatives Based on 2,4′-Biphenylene Linker with Quinoxaline, [1,2,5]Oxadiazolo[3,4-B]Pyrazine and [1,2,5]Thiadiazolo[3,4-B]Pyrazine Electron Withdrawing Parts
Egor V. Verbitskiy
1, 2
,
Pascal Le Poul
3
,
Filip Bures
4
,
Sylvain Achelle
3
,
A. Barsella
5
,
Yuriy A Kvashnin
1
,
Gennady L. Rusinov
1, 2
,
Valery Charushin
1, 2
3
Publication type: Journal Article
Publication date: 2022-06-30
PubMed ID:
35807494
Organic Chemistry
Drug Discovery
Physical and Theoretical Chemistry
Pharmaceutical Science
Molecular Medicine
Analytical Chemistry
Chemistry (miscellaneous)
Abstract
A series of novel V-shaped quinoxaline, [1,2,5]oxadiazolo[3,4-b]pyrazine and [1,2,5]thiadiazolo[3,4-b]pyrazine push–pull derivatives with 2,4′-biphenylene linker were designed and their electrochemical, photophysical and nonlinear optical properties were investigated. [1,2,5]Oxadiazolo[3,4-b]pyrazine is the stronger electron-withdrawing fragment as shown by electrochemical, and photophysical data. All compounds are emissive in a solid-state (from the cyan to red region of the spectrum) and quinoxaline derivatives are emissions in DCM solution. It has been found that quinoxaline derivatives demonstrate important solvatochromism and extra-large Stokes shifts, characteristic of twisted intramolecular charge transfer excited state as well as aggregation induced emission. The experimental conclusions have been justified by theoretical (TD-)DFT calculations.
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26
Total citations:
26
Citations from 2024:
14
(53.85%)
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GOST
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Verbitskiy E. V. et al. Push–Pull Derivatives Based on 2,4′-Biphenylene Linker with Quinoxaline, [1,2,5]Oxadiazolo[3,4-B]Pyrazine and [1,2,5]Thiadiazolo[3,4-B]Pyrazine Electron Withdrawing Parts // Molecules. 2022. Vol. 27. No. 13. p. 4250.
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Verbitskiy E. V., Le Poul P., Bures F., Achelle S., Barsella A., Kvashnin Y. A., Rusinov G. L., Charushin V. Push–Pull Derivatives Based on 2,4′-Biphenylene Linker with Quinoxaline, [1,2,5]Oxadiazolo[3,4-B]Pyrazine and [1,2,5]Thiadiazolo[3,4-B]Pyrazine Electron Withdrawing Parts // Molecules. 2022. Vol. 27. No. 13. p. 4250.
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RIS
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TY - JOUR
DO - 10.3390/molecules27134250
UR - https://doi.org/10.3390/molecules27134250
TI - Push–Pull Derivatives Based on 2,4′-Biphenylene Linker with Quinoxaline, [1,2,5]Oxadiazolo[3,4-B]Pyrazine and [1,2,5]Thiadiazolo[3,4-B]Pyrazine Electron Withdrawing Parts
T2 - Molecules
AU - Verbitskiy, Egor V.
AU - Le Poul, Pascal
AU - Bures, Filip
AU - Achelle, Sylvain
AU - Barsella, A.
AU - Kvashnin, Yuriy A
AU - Rusinov, Gennady L.
AU - Charushin, Valery
PY - 2022
DA - 2022/06/30
PB - MDPI
SP - 4250
IS - 13
VL - 27
PMID - 35807494
SN - 1420-3049
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2022_Verbitskiy,
author = {Egor V. Verbitskiy and Pascal Le Poul and Filip Bures and Sylvain Achelle and A. Barsella and Yuriy A Kvashnin and Gennady L. Rusinov and Valery Charushin},
title = {Push–Pull Derivatives Based on 2,4′-Biphenylene Linker with Quinoxaline, [1,2,5]Oxadiazolo[3,4-B]Pyrazine and [1,2,5]Thiadiazolo[3,4-B]Pyrazine Electron Withdrawing Parts},
journal = {Molecules},
year = {2022},
volume = {27},
publisher = {MDPI},
month = {jun},
url = {https://doi.org/10.3390/molecules27134250},
number = {13},
pages = {4250},
doi = {10.3390/molecules27134250}
}
Cite this
MLA
Copy
Verbitskiy, Egor V., et al. “Push–Pull Derivatives Based on 2,4′-Biphenylene Linker with Quinoxaline, [1,2,5]Oxadiazolo[3,4-B]Pyrazine and [1,2,5]Thiadiazolo[3,4-B]Pyrazine Electron Withdrawing Parts.” Molecules, vol. 27, no. 13, Jun. 2022, p. 4250. https://doi.org/10.3390/molecules27134250.