First Alliance of Pyrazole and Furoxan Leading to High-Performance Energetic Materials

First Alliance of Pyrazole and Furoxan Leading to High-Performance Energetic Materials Full article

Journal

ACS Applied Materials & Interfaces
ISSN: 1944-8244 , E-ISSN: 1944-8252

Output data

Year: 2024, Volume: 16, Number: 40, Pages: 53972–53979 Pages count : DOI: 10.1021/acsami.4c12242

Authors

Khoranyan Tigran E. ¹ , Larin Alexander A. ¹ , Suponitsky Kyrill Yu. ² , Ananyev Ivan V. ^2,3 , Melnikov Igor N. ⁴ , Kosareva Ekaterina K. ⁴ , Muravyev Nikita V. ⁴ , Dalinger Igor L. ¹ , Pivkina Alla N. ⁴ , Fershtat Leonid L. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prosp. 47, Moscow 119991, Russian Federation
2	A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilova Str. 28, Moscow 119991, Russian Federation
3	N.S. Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, Leninsky prosp. 31, Moscow 119991, Russian Federation
4	N. N. Semenov Federal Research Centre for Chemical Physics, Russian Academy of Sciences, Kosygin Str. 4, Moscow 119991, Russian Federation

Nitrogen heterocyclic scaffolds retain their leading position as valuable building blocks in material science, particularly for the design of small-molecule energetic materials. However, the search for more balanced combinations of directly linked heterocyclic cores is far from being exhausted and aims to reach ideally balanced high-energy substances. Herein, we present the synthetic route to novel pyrazole-furoxan framework enriched with nitro groups and demonstrate a promising set of properties, viz., good thermal stability, acceptable mechanical sensitivity, and high detonation performance. In-depth crystal analysis showed that the isomers having lower-impact sensitivity values in both types of regioisomeric pairs are those with the exocyclic furoxan oxygen atom being closer to the pyrazole ring. Owing to the favorable combination of high crystal densities (1.83–1.93 g cm–3), positive oxygen balance to CO (up to +13.9%), and high enthalpies of formation (322–435 kJ mol–1), the synthesized compounds show high calculated detonation velocities (8.4–9.1 km s–1) and excellent metal accelerating abilities. The incorporation of the 3-nitrofuroxan moiety increases the thermal stability (by ca. 20 °C) and decreases the mechanical sensitivity of target hybrid materials in both types of regioisomeric pairs. Simultaneously, the detonation performance of 3-nitrofuroxans is almost identical to that of 4-nitrofuroxans, highlighting the potential of the regioisomeric tunability in the future design of energetic materials.

Khoranyan T.E. , Larin A.A. , Suponitsky K.Y. , Ananyev I.V. , Melnikov I.N. , Kosareva E.K. , Muravyev N.V. , Dalinger I.L. , Pivkina A.N. , Fershtat L.L.
First Alliance of Pyrazole and Furoxan Leading to High-Performance Energetic Materials
ACS Applied Materials & Interfaces. 2024. V.16. N40. P.53972–53979. DOI: 10.1021/acsami.4c12242 WOS Scopus OpenAlex

Web of science:	WOS:001320383900001
Scopus:	2-s2.0-85205906286
OpenAlex:	W4402849783

DB	Citing
OpenAlex	11
Scopus	9
Web of science	9