Stable anion radicals based on a triazole-fused furazano[3,4-b]pyrazine scaffold

Stable anion radicals based on a triazole-fused furazano[3,4-b]pyrazine scaffold Full article

Journal

New Journal of Chemistry
ISSN: 1369-9261 , E-ISSN: 1144-0546

Output data

Year: 2025, Volume: 49, Number: 10, Pages: 3869-3876 Pages count : 8 DOI: 10.1039/D4NJ05188B

Authors

Efanov D.E. ¹ , Tokstikov S.E. ¹ , Romasnenko G.V. ¹ , Letyagin G.A. ¹ , Smirnova K.A. ¹ , Chernavin P.A. ¹ , Veber S.L. ¹ , Romashev N.F. ² , Osik N.A. ¹ , Bogomyakov A.S. ¹

Affiliations

1	International Tomography Center of the Siberian Branch of the Russian Academy of Sciences, Institutskaya Str., 3A, Novosibirsk, Russian Federation
2	Nikolaev Institute of Inorganic Chemistry of the Siberian Branch of Russian Academy of Sciences, Acad. Lavrentiev Ave., 3, Novosibirsk, Russian Federation

A completely original open-shell scaffold, based on the furazano[3,4-b]pyrazine moiety, has been recently discovered and has already shown certain advantages over mainstay radical blocks. Here, we present a way to synthetically extend this class by changing an oxadiazole moiety into a triazole, yielding triazolo[4,5-e]furazano[3,4-b]pyrazines, thereby unlocking a site for substituents in the scaffold. We also propose new transformation conditions for the key cyclization step of bis(arylhydrazones) to the corresponding 6-aryltriazolo[4,5-e]furazano[3,4-b]pyrazines. The anion radicals, resulting from their easy one-electron oxidation, exhibit good stability and unexpected NIR luminescence.

Efanov D.E. , Tokstikov S.E. , Romasnenko G.V. , Letyagin G.A. , Smirnova K.A. , Chernavin P.A. , Veber S.L. , Romashev N.F. , Osik N.A. , Bogomyakov A.S.
Stable anion radicals based on a triazole-fused furazano[3,4-b]pyrazine scaffold
New Journal of Chemistry. 2025. Т.49. №10. С.3869-3876. DOI: 10.1039/D4NJ05188B OpenAlex

Submitted:	Dec 3, 2024
Accepted:	Jan 30, 2025
Published online:	Feb 3, 2025
Published print:	Mar 14, 2025

OpenAlex:

W4407080637

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