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.
Highlights
Nitrogen-rich heterocycles are one of the most intriguing groups of compounds in organic chemistry
This feature can be used in the production of organic light-emitting diodes (OLEDs), organic field-effect transistors (OFETs), or solar cells
Our previous research showed that the route using diacylhydrazine derivatives is a very favorable pathway for the synthesis of s-tetrazine derivatives conjugated via a
Summary
Nitrogen-rich heterocycles are one of the most intriguing groups of compounds in organic chemistry. In recent years, s-tetrazine-containing compounds have been intensively researched in terms of their applicability in medicine (due to their anti-tuberculosis, anti-cancer, or anti-malaria effects) [4,5,6], bio-orthogonal chemistry (as aconsequence of their high reactivity in Diels-Alder reactions with inverse electron demand) [7,8,9,10] and optoelectronics. Their potential applications in the latter area are strongly related to their characteristic low-energy n→π electronic transitions. Many scientists are currently working on the synthesis of new s-tetrazine structures with superior properties
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