Synthesis, Photophysical, and (Spectro)Electrochemical Properties of New Benzo[1,2-c][1,2,5]thiadiazoles and Benzo[1,2-d][1,2,3]triazoles Fused with Two Thiazole Rings
Anastasia S. Kostyuchenko
1, 2
,
Evgenii B. Uliankin
1, 2
,
E. B. Uliankin
1, 2
,
Antony J. Stasyuk
3, 4
,
Alexander S. Fisyuk
1, 2
Publication type: Journal Article
Publication date: 2023-04-18
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
37070610
Organic Chemistry
Abstract
Acylation of benzo[c][1,2,5]thiadiazole-4,7-diamine and 2-hexyl-2H-benzo[d][1,2,3]triazole-4,7-diamine with aromatic acid halides furnished the corresponding N,N'-diamides, which were converted into N,N'-dithioamides by reacting with Lawesson's reagent. A method was developed for the preparation of previously unknown fused systems, dithiazolobenzo[1,2-c][1,2,5]thiadiazoles and dithiazolobenzo[1,2-d][1,2,3]triazoles, by oxidative photochemical cyclization of N,N'-dithioamides. The photophysical and (spectro)electrochemical properties of the obtained compounds and their polymer films electrochemically deposited on ITO were studied. The optical contrast and response time of the synthesized oligomers were determined. The results obtained allow us to consider these substances as promising candidates for electrochromic devices.
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Kostyuchenko A. S. et al. Synthesis, Photophysical, and (Spectro)Electrochemical Properties of New Benzo[1,2-c][1,2,5]thiadiazoles and Benzo[1,2-d][1,2,3]triazoles Fused with Two Thiazole Rings // Journal of Organic Chemistry. 2023. Vol. 88. No. 9. pp. 5875-5892.
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Kostyuchenko A. S., Uliankin E. B., Uliankin E. B., Stasyuk A. J., Zheleznova T. Y., Fisyuk A. S. Synthesis, Photophysical, and (Spectro)Electrochemical Properties of New Benzo[1,2-c][1,2,5]thiadiazoles and Benzo[1,2-d][1,2,3]triazoles Fused with Two Thiazole Rings // Journal of Organic Chemistry. 2023. Vol. 88. No. 9. pp. 5875-5892.
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TY - JOUR
DO - 10.1021/acs.joc.3c00286
UR - https://pubs.acs.org/doi/10.1021/acs.joc.3c00286
TI - Synthesis, Photophysical, and (Spectro)Electrochemical Properties of New Benzo[1,2-c][1,2,5]thiadiazoles and Benzo[1,2-d][1,2,3]triazoles Fused with Two Thiazole Rings
T2 - Journal of Organic Chemistry
AU - Kostyuchenko, Anastasia S.
AU - Uliankin, Evgenii B.
AU - Uliankin, E. B.
AU - Stasyuk, Antony J.
AU - Zheleznova, Tatyana Yu.
AU - Fisyuk, Alexander S.
PY - 2023
DA - 2023/04/18
PB - American Chemical Society (ACS)
SP - 5875-5892
IS - 9
VL - 88
PMID - 37070610
SN - 0022-3263
SN - 1520-6904
ER -
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@article{2023_Kostyuchenko,
author = {Anastasia S. Kostyuchenko and Evgenii B. Uliankin and E. B. Uliankin and Antony J. Stasyuk and Tatyana Yu. Zheleznova and Alexander S. Fisyuk},
title = {Synthesis, Photophysical, and (Spectro)Electrochemical Properties of New Benzo[1,2-c][1,2,5]thiadiazoles and Benzo[1,2-d][1,2,3]triazoles Fused with Two Thiazole Rings},
journal = {Journal of Organic Chemistry},
year = {2023},
volume = {88},
publisher = {American Chemical Society (ACS)},
month = {apr},
url = {https://pubs.acs.org/doi/10.1021/acs.joc.3c00286},
number = {9},
pages = {5875--5892},
doi = {10.1021/acs.joc.3c00286}
}
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MLA
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Kostyuchenko, Anastasia S., et al. “Synthesis, Photophysical, and (Spectro)Electrochemical Properties of New Benzo[1,2-c][1,2,5]thiadiazoles and Benzo[1,2-d][1,2,3]triazoles Fused with Two Thiazole Rings.” Journal of Organic Chemistry, vol. 88, no. 9, Apr. 2023, pp. 5875-5892. https://pubs.acs.org/doi/10.1021/acs.joc.3c00286.