Parent 1,4-dihydro-[1,2,3]triazolo[4,5-d][1,2,3]triazole and its derivatives as precursors for the design of promising high energy density materials

Parent 1,4-dihydro-[1,2,3]triazolo[4,5-d][1,2,3]triazole and its derivatives as precursors for the design of promising high energy density materials Full article

Journal

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

Output data

Year: 2025, Volume: 49, Number: 1, Pages: 311-320 Pages count : 10 DOI: 10.1039/d4nj04427d

Authors

Kuznetsova Agata N. ^1,2 , Leonov Nikita E. ² , Anikin Oleg V. ² , Klenov Michael S. ² , Churakov Aleksandr M. ² , Strelenko Yurii A. ² , Novikov Roman A. ² , Fedyanin Ivan V. ³ , Pivkina Alla N. ⁴ , Kon’kova Tatiana S. ⁴ , Sinditskii Valery P. ⁵ , Smirnova Anastasia D. ⁵ , Tartakovsky Vladimir A. ²

Affiliations

1	Department of Chemistry, Lomonosov Moscow State University, 1 Leninskie Gory, Moscow, 119991, Russian Federation
2	N. D. Zelinsky Institute of Organic Chemistry Russian Academy of Sciences, 47 Leninsky prospect, Moscow, 119991, Russian Federation
3	A. N. Nesmeyanov Institute of Organoelement Compounds Russian Academy of Sciences, 28 Vavilova st., Moscow, 119991, Russian Federation
4	N. N. Semenov Federal Research Center for Chemical Physics Russian Academy of Sciences, 4 Kosygin st., Moscow, 119991, Russian Federation
5	Mendeleev University of Chemical Technology, 9 Miusskaya Square, Moscow, 125047, Russian Federation

The design of novel high energy density materials (HEDMs) is still one of the significant challenges in the field of applied chemistry. Newly discovered scaffolds are rare, but they open up new possibilities for HEDM design. Herein, a simple and effective two-step approach to previously unknown 1,4-dihydro-[1,2,3]triazolo[4,5-d][1,2,3]triazole (1) is presented. This compound is an individual energetic material (d = 1.84 g cm−3, Image ID:d4nj04427d-t1.gif, Tonset = 193 °C (all experimental values), D = 8.5 km s−1, P = 34 GPa (calculated ones)), but may also serve as a scaffold for the synthesis of structurally diversified related compounds. The precursors of triazolo–triazole 1 are previously unknown 5-amino-4-diazo-4H-1,2,3-triazolium chloride (4) and 5-amino-4-diazo-4H-1,2,3-triazole (5), which can also serve as starting materials for the synthesis of a variety of novel heterocycles. For example, the diazo compound 5 was used for the regioselective synthesis of a 2,5-disubstituted triazolo–triazole 10 bearing an N4-tripoid fragment. Overall, the developed approach to triazolo–triazole 1, 5-amino-4-diazo-4H-1,2,3-triazolium chloride (4) and 5-amino-4-diazo-4H-1,2,3-triazole (5) is expected to make these high nitrogen systems more accessible and affordable for the design of nitrogen containing fused heterocycles.

Kuznetsova A.N. , Leonov N.E. , Anikin O.V. , Klenov M.S. , Churakov A.M. , Strelenko Y.A. , Novikov R.A. , Fedyanin I.V. , Pivkina A.N. , Kon’kova T.S. , Sinditskii V.P. , Smirnova A.D. , Tartakovsky V.A.
Parent 1,4-dihydro-[1,2,3]triazolo[4,5-d][1,2,3]triazole and its derivatives as precursors for the design of promising high energy density materials
New Journal of Chemistry. 2025. V.49. N1. P.311-320. DOI: 10.1039/d4nj04427d WOS Scopus OpenAlex

≡ Web of science:	WOS:001369392800001
≡ Scopus:	2-s2.0-85211022629
≡ OpenAlex:	W4404737617