Linear furoxan assemblies incorporating nitrobifuroxan scaffold: En route to new high-performance energetic materials

Linear furoxan assemblies incorporating nitrobifuroxan scaffold: En route to new high-performance energetic materials Научная публикация

Журнал

Chemical Engineering Journal
ISSN: 1873-3212 , E-ISSN: 1385-8947

Вых. Данные

Год: 2023, Том: 470, Номер статьи : 144144, Страниц : DOI: 10.1016/j.cej.2023.144144

Авторы

Larin Alexander A. ^1,2 , Degtyarev Daniil D. ^3,1 , Ananyev Ivan V. ^4,2 , Pivkina Alla N. ⁵ , Fershtat Leonid L. ¹

Организации

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prosp. 47, Moscow 119991, Russian Federation
2	National Research University Higher School of Economics, 101000, Myasnitskaya str., 20, Moscow, Russian Federation
3	Department of Chemistry, Moscow State University, 119991 Leninskie Gory 1-3, Moscow, Russian Federation
4	N.S. Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, GSP-1, Leninsky prospect, 31, 119991 Moscow, Russian Federation
5	N. N. Semenov Federal Research Centre for Chemical Physics, Russian Academy of Sciences, 4 Kosygin Str., Moscow 119991, Russian Federation

Energetic materials science is undergoing a global renaissance aiming to reach an ideal combination between reliable synthetic strategies, high performance and acceptable molecular stabilities. In this work, design and synthesis of novel energetic non-hydrogen furoxan assemblies has been successfully realized. Fine tunability of molecular composition in a series of furoxan-based materials was achieved by the variation of a number of heterocyclic rings and employing N-oxide regioisomerism strategy. Using this approach, advanced energetic regioisomeric azo-bridged bifuroxan assemblies 6 and 7 as well as 3,4′-dinitro-3′,4-bifuroxan 8 with the excellent overall performance were synthesized. Calculations of Hirshfeld surfaces and molecular electrostatic potentials were conducted to better understand the relationship between the molecular structure and mechanical sensitivity in the synthesized series of energetic materials. It was found, that the supramolecular aggregation of 3,4′-dinitro-3′,4-bifuroxan 8 molecules in crystal is more anisotropic that is commonly believed to be more favorable pattern for the low sensitive substances. All target materials have high densities (1.88–1.95 g cm−3), acceptable thermal stabilities (up to 165 °C), high enthalpies of formation (1.6–2.4 kJ g−1) and positive oxygen balance to CO (up to + 25%). As a result, these compounds exhibit high detonation velocities (9.1–9.5 km s−1), excellent heats of explosion (6.6–7.2 kJ g−1) and combustion performance (Isp = 269–281 s). Therefore, these furoxan-based advanced energetic materials unveil new opportunities in search of next-generation functional organic materials for various applications.

Larin A.A. , Degtyarev D.D. , Ananyev I.V. , Pivkina A.N. , Fershtat L.L.
Linear furoxan assemblies incorporating nitrobifuroxan scaffold: En route to new high-performance energetic materials
Chemical Engineering Journal. 2023. V.470. 144144 . DOI: 10.1016/j.cej.2023.144144 WOS Scopus OpenAlex

Web of science:	WOS:001040670600001
Scopus:	2-s2.0-85163568129
OpenAlex:	W4381851087

БД	Цитирований
OpenAlex	41
Scopus	39
Web of science	40