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Article

Novel Conjugated s-Tetrazine Derivatives Bearing a 4H-1,2,4-Triazole Scaffold: Synthesis and Luminescent Properties

by
Anna Maj
1,
Agnieszka Kudelko
1,* and
Marcin Świątkowski
2
1
Department of Chemical Organic Technology and Petrochemistry, The Silesian University of Technology, Krzywoustego 4, PL-44100 Gliwice, Poland
2
Institute of General and Ecological Chemistry, Lodz University of Technology, Zeromskiego 116, PL-90924 Lodz, Poland
*
Author to whom correspondence should be addressed.
Molecules 2022, 27(2), 459; https://doi.org/10.3390/molecules27020459
Submission received: 9 December 2021 / Revised: 6 January 2022 / Accepted: 7 January 2022 / Published: 11 January 2022
(This article belongs to the Section Organic Chemistry)
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Abstract

A series of new symmetrical s-tetrazine derivatives, coupled via a 1,4-phenylene linkage with a 4H-1,2,4-triazole ring, were obtained. The combination of these two rings in an extensively coupled system has significant potential applications, mainly in optoelectronics. The methodology used turned out to be useful regardless of the type of five-membered ring or the nature of the individual substituents. All the products were identified by spectroscopic methods, and the target compounds were tested for luminescent properties. This study showed that all the synthesized highly-conjugated triazoles exhibited luminescence; in particular, one derivative, 3,6-bis(4-(5-(4-methoxyphenyl)-4-phenyl-4H-1,2,4-triazol-3-yl)phenyl)-1,2,4,5-tetrazine (13b), showed strong fluorescence emission and ahigh quantum yield close to 1.
Keywords: s-tetrazine; 4H-1,2,4-triazole; Pinner reaction s-tetrazine; 4H-1,2,4-triazole; Pinner reaction
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MDPI and ACS Style

Maj, A.; Kudelko, A.; Świątkowski, M. Novel Conjugated s-Tetrazine Derivatives Bearing a 4H-1,2,4-Triazole Scaffold: Synthesis and Luminescent Properties. Molecules 2022, 27, 459. https://doi.org/10.3390/molecules27020459

AMA Style

Maj A, Kudelko A, Świątkowski M. Novel Conjugated s-Tetrazine Derivatives Bearing a 4H-1,2,4-Triazole Scaffold: Synthesis and Luminescent Properties. Molecules. 2022; 27(2):459. https://doi.org/10.3390/molecules27020459

Chicago/Turabian Style

Maj, Anna, Agnieszka Kudelko, and Marcin Świątkowski. 2022. "Novel Conjugated s-Tetrazine Derivatives Bearing a 4H-1,2,4-Triazole Scaffold: Synthesis and Luminescent Properties" Molecules 27, no. 2: 459. https://doi.org/10.3390/molecules27020459

APA Style

Maj, A., Kudelko, A., & Świątkowski, M. (2022). Novel Conjugated s-Tetrazine Derivatives Bearing a 4H-1,2,4-Triazole Scaffold: Synthesis and Luminescent Properties. Molecules, 27(2), 459. https://doi.org/10.3390/molecules27020459

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