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New D–A–D luminophores of the [1,2,5]thiadiazolo[3,4-d]pyridazine series

Vladislav Mikailovich Korshunov 1
Vladislav Mikailovich Korshunov
Timofey Nikolaevich Chmovzh
German R Chkhetiani 2
German R Chkhetiani
Il'ya Viktorovich Taidakov 1
Il'ya Viktorovich Taidakov
Oleg Alexeevich Rakitin 2
Oleg Alexeevich Rakitin
Published 2022-04-29
CommunicationVolume 32, Issue 3, 371-373
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Korshunov V. M. et al. New D–A–D luminophores of the [1,2,5]thiadiazolo[3,4-d]pyridazine series // Mendeleev Communications. 2022. Vol. 32. No. 3. pp. 371-373.
GOST all authors (up to 50) Copy
Korshunov V. M., Chmovzh T. N., Chkhetiani G. R., Taidakov I. V., Rakitin O. A. New D–A–D luminophores of the [1,2,5]thiadiazolo[3,4-d]pyridazine series // Mendeleev Communications. 2022. Vol. 32. No. 3. pp. 371-373.
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TY - JOUR
DO - 10.1016/j.mencom.2022.05.026
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2022.05.026
TI - New D–A–D luminophores of the [1,2,5]thiadiazolo[3,4-d]pyridazine series
T2 - Mendeleev Communications
AU - Korshunov, Vladislav Mikailovich
AU - Chmovzh, Timofey Nikolaevich
AU - Chkhetiani, German R
AU - Taidakov, Il'ya Viktorovich
AU - Rakitin, Oleg Alexeevich
PY - 2022
DA - 2022/04/29
PB - Mendeleev Communications
SP - 371-373
IS - 3
VL - 32
ER -
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@article{2022_Korshunov,
author = {Vladislav Mikailovich Korshunov and Timofey Nikolaevich Chmovzh and German R Chkhetiani and Il'ya Viktorovich Taidakov and Oleg Alexeevich Rakitin},
title = {New D–A–D luminophores of the [1,2,5]thiadiazolo[3,4-d]pyridazine series},
journal = {Mendeleev Communications},
year = {2022},
volume = {32},
publisher = {Mendeleev Communications},
month = {Apr},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2022.05.026},
number = {3},
pages = {371--373},
doi = {10.1016/j.mencom.2022.05.026}
}
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Korshunov, Vladislav Mikailovich, et al. “New D–A–D luminophores of the [1,2,5]thiadiazolo[3,4-d]pyridazine series.” Mendeleev Communications, vol. 32, no. 3, Apr. 2022, pp. 371-373. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2022.05.026.

Keywords

[1,2,5]thiadiazolo[3,4-d]pyridazines
aromatic nucleophilic substitution
donor–acceptor–donor structure
indoles
luminescence
NIR-OLEDs
synthesis

Abstract

Three [1,2,5]thiadiazolo[3,4-d]pyridazines containing 4,7-positioned indole-type substituents were synthesized from the corresponding 4,7-dibromo precursor employing the SNAr aromatic nucleophilic substitution. Photophysical properties and DFT calculations showed that the D–A–D dyes based on [1,2,5]thiadiazolo[3,4-d]pyridazine core exhibited fluorescence in the near infrared region of the spectrum, which makes them promising for use as an active emitting layer in NIR-OLEDs as well as for other possible applications as an IR luminophore.

References

2.
Dye-sensitized solar cells: Investigation of D-A-Π-A organic sensitizers based on [1,2,5]selenadiazolo[3,4-c]pyridine
Knyazeva E.A., Wu W., Chmovzh T.N., Robertson N., Woollins J.D., Rakitin O.A.
Solar Energy, 2017
3.
(c) B. A. D. Neto, A. A. M. Lapis, E. N. da Silva, Jr., and J. Dupont, Eur. J. Org. Chem., 2013, 228
5.
Metal-Free Sensitizers for Dye-Sensitized Solar Cells
6.
(a) A. V. Akkuratov and P. A. Troshin, Polym. Sci., Ser. B, 2014, 56, 414 (Vysokomol. Soedin., Ser. B, 2014, 56, 371); (b) G. V. Bulavko and A. A. Ishchenko, Russ. Chem. Rev., 2014, 83, 575; (c) T. P. Le, B. H. Smith, Y. Lee, J. H. Litofsky, M. P. Aplan, B. Kuei, C. Zhu, C. Wang, A. Hexemer and E. D. Gomez, Macromolecules, 2020, 53, 1967; (d) W. Xu, Y. Chang, X. Zhu, Z. Wei, X. Zhang, X. Sun, K. Lu and Z. Wei, Chin. Chem. Lett., 2022, 33, 123; (e) A. Wadsworth, Z. Hamid, J. Kosco, N. Gasparini and I. McCulloch, Adv. Mater., 2020, 32, 2001763.
7.
A Conjugated Polymer Containing a B ← N Unit for Unipolar n-Type Organic Field-Effect Transistors
Zhao R., Min Y., Dou C., Lin B., Ma W., Liu J., Wang L.
ACS Applied Polymer Materials, 2019
8.
A novel low-bandgap pyridazine thiadiazole-based conjugated polymer with deep molecular orbital levels
Leventis A., Chmovzh T.N., Knyazeva E.A., Han Y., Heeney M., Rakitin O.A., Bronstein H.
Polymer Chemistry, 2020
10.
Candle light-style OLEDs with benzochalcogenadiazoles cores
Korshunov V.M., Chmovzh T.N., Golovanov I.S., Knyazeva E.A., Mikhalchenko L.V., Saifutyarov R.S., Avetisov I.C., Woollins J.D., Taydakov I.V., Rakitin O.A.
Dyes and Pigments, 2021
11.
Superiority of D–A–D over D–A type of organic dyes for the application in dye-sensitized solar cell
Biswas S., Pramanik A., Ahmed T., Sahoo S.K., Sarkar P.
Chemical Physics Letters, 2016
13.
Gribanov P.S., Lypenko D.A., Dmitriev A.V., Pozin S.I., Topchiy M.A., Asachenko A.F., Loginov D.A., Osipov S.N.
Mendeleev Communications, 2021
15.
Efficient Near‐Infrared Electroluminescence at 840 nm with “Metal‐Free” Small‐Molecule:Polymer Blends
Minotto A., Murto P., Genene Z., Zampetti A., Carnicella G., Mammo W., Andersson M.R., Wang E., Cacialli F.
Advanced Materials, 2018
16.
New Benzo[1,2-d:4,5-d′]bis([1,2,3]thiadiazole) (iso-BBT)-Based Polymers for Application in Transistors and Solar Cells
Bianchi L., Zhang X., Chen Z., Chen P., Zhou X., Tang Y., Liu B., Guo X., Facchetti A.
Chemistry of Materials, 2019
17.
Synthesis of the 4,7-Dibromo Derivative of Highly Electron-Deficient [1,2,5]Thiadiazolo[3,4-d]pyridazine and Its Cross-Coupling Reactions
Chmovzh T.N., Knyazeva E.A., Mikhalchenko L.V., Golovanov I.S., Amelichev S.A., Rakitin O.A.
European Journal of Organic Chemistry, 2018
18.
Reactions of 4,7-dibromo[1,2,5]thiadiazolo[3,4-d]pyridazine with alcohols
Chmovzh T.N., Knyazeva E.A., Krukovskaya N.V., Rakitin O.A.
Russian Chemical Bulletin, 2020
19.
Safe synthesis of 4,7-dibromo[1,2,5]thiadiazolo [3,4-d]pyridazine and its SNAr reactions
Chmovzh T., Knyazeva E., Lyssenko K., Popov V., Rakitin O.
Molecules, 2018