Design and Synthesis of Nitrogen‐Rich Azo‐Bridged Furoxanylazoles as High‐Performance Energetic Materials

Design and Synthesis of Nitrogen‐Rich Azo‐Bridged Furoxanylazoles as High‐Performance Energetic Materials Научная публикация

Журнал

Chemistry: A European Journal
ISSN: 0947-6539 , E-ISSN: 1521-3765

Вых. Данные

Год: 2021, Том: 27, Номер: 59, Страницы: 14628-14637 Страниц : 10 DOI: 10.1002/chem.202101987

Авторы

Larin Alexander A. ¹ , Shaferov Alexander V. ¹ , Kulikov Alexander S. ¹ , Pivkina Alla N. ² , Monogarov Konstantin A. ² , Dmitrienko Artem O. ³ , Ananyev Ivan V. ^4,5 , Khakimov Dmitry V. ¹ , Fershtat Leonid L. ¹ , Makhova Nina N. ¹

Организации

1	N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991, Leninsky prospect, 47, Moscow (Russia)
2	N. N. Semenov Federal Research Center for Chemical Physics, Russian Academy of Sciences, 119991, Kosygin str., 4, Moscow, Russia.
3	Department of Chemistry, M. V. Lomonosov Moscow State University, 119991, Leninskie Gory, 1-3, Moscow, Russia.
4	A. N. Nesmeyanov Institute of Organoelement Compounds Russian Academy of Sciences 119991 Vavilova str., 28 Moscow Russia
5	National Research University Higher School of Economics 101000 Myasnitskaya str., 20 Moscow Russia

A series of novel energetic materials comprising of azo-bridged furoxanylazoles enriched with energetic functionalities was designed and synthesized. These high-energy materials were thoroughly characterized by IR and multinuclear NMR (1H, 13C, 14N) spectroscopy, high-resolution mass spectrometry, elemental analysis, and differential scanning calorimetry (DSC). The molecular structures of representative amino and azo oxadiazole assemblies were additionally confirmed by single-crystal X-ray diffraction and X-ray powder diffraction. A comparison of contributions of explosophoric moieties into the density of energetic materials revealed that furoxan and 1,2,4-oxadiazole rings are the densest motifs while the substitution of the azide and amino fragments on the nitro and azo ones leads to an increase of the density. Azo bridged energetic materials have high nitrogen-oxygen contents (68.8–76.9 %) and high thermal stability. The synthesized compounds exhibit good experimental densities (1.62–1.88 g cm−3), very high enthalpies of formation (846–1720 kJ mol−1), and, as a result, excellent detonation performance (detonation velocities 7.66–9.09 km s−1 and detonation pressures 25.0–37.7 GPa). From the application perspective, the detonation parameters of azo oxadiazole assemblies exceed those of the benchmark explosive RDX, while a combination of high detonation performance and acceptable friction sensitivity of azo(1,2,4-triazolylfuroxan) make it a promising potential alternative to PETN.

Larin A.A. , Shaferov A.V. , Kulikov A.S. , Pivkina A.N. , Monogarov K.A. , Dmitrienko A.O. , Ananyev I.V. , Khakimov D.V. , Fershtat L.L. , Makhova N.N.
Design and Synthesis of Nitrogen‐Rich Azo‐Bridged Furoxanylazoles as High‐Performance Energetic Materials
Chemistry: A European Journal. 2021. V.27. N59. P.14628-14637. DOI: 10.1002/chem.202101987 WOS Scopus OpenAlex

Web of science:	WOS:000701304500001
Scopus:	2-s2.0-85116188752
OpenAlex:	W3187011066

БД	Цитирований
OpenAlex	39
Scopus	40
Web of science	38