Construction of Coplanar Bicyclic Backbones for 1,2,4‐Triazole‐1,2,4‐Oxadiazole‐Derived Energetic Materials

Abstract

Combining different nitrogen‐rich heterocycles into a molecule can fine‐tune its energetic performance and physical properties as well as its safety for use in energetic materials. Here, 1,2,4‐oxadiazole was incorporated into 1,2,4‐triazole to construct new energetic backbones. 3‐(5‐Amino‐1H‐1,2,4‐triazol‐3‐yl)‐1,2,4‐oxadiazol‐5‐amine (5) was designed and synthesized. Nitramino‐functionalized N‐(5‐(5‐amino‐1,2,4‐oxadiazol‐3‐yl)‐3H‐1,2,4‐triazol‐3‐yl)nitramide (6) and N‐(5‐(5‐(nitramino)‐1,2,4‐oxadiazol‐3‐yl)‐3H‐1,2,4‐triazol‐3‐yl)nitramide (7) were also obtained, and two series of corresponding nitrogen‐rich salts were prepared, leading to the creation of new energetic compounds. All derivatives were fully characterized, and five of them were further confirmed by X‐ray diffraction. The theoretical calculations, energetic performance, safety, and the main decomposition gaseous products of 1,2,4‐triazole‐1,2,4‐oxadiazole‐derived energetic materials were studied. Compound 7 and its dihydroxylammonium salt (7 c) exhibited prominent detonation performance comparable to that of RDX while possessing satisfying thermal stabilities and mechanical sensitivities.

Preparation of Laser Energetic Coordination Polymers Based on Urazine by Self-Crystallization

“…It is concluded that the main decomposition products are H 2 O (ν = 3544, 3510 cm −1 ) and CO (ν = 2183, 2150 cm −1 ). 27 This can be reasonably explained as follows: (1) AgCl becomes a molten liquid state at 445 °C. (2) Since the test material we used is an aluminum crucible, AgCl and Al undergo a substitution reaction to obtain Ag and AlCl 3 , and AlCl 3 is a gaseous compound at this temperature, so the quality is lost.…”

1‐Nitrimino‐5‐azidotetrazole: Extending Energetic Tetrazole Chemistry

“…[35] Nor could the protect-Scheme 1. Synthesis of 1-amino-5-azidotetrazole (1) through diazotization of triaminoguanidinium chloride and nitration using mixed acid to 1-nitrimino-5-azidotetrazole (2).…”

“…Alongside ever greater efforts to develop more powerful explosives, the environmental aspect in particular is a central factor for the development of new energetic materials. [1][2][3] For this, some basic properties should be fulfilled, whereby newly developed substances should be free of heavy metals and perchlorates. Compounds containing these components are demonstrably harmful to the environment and hazardous to humans' health.…”

Fast explosive performance prediction via small-dose energetic materials based on time-resolved imaging combined with machine learning

“…Samples D1 to D9 were conventional single-compound explosives with higher detonation performance than the tetrazole EMs labeled as D10 to D17. A set of novel constructed coplanar bicyclic backbones for 1,2,4-triazole-1,2,4-oxadiazole-derived high nitrogen energetic compounds 19 were marked as D18 to D27. Besides, their typical detonation parameters, including DV, HoD, VoD, DP, and DT, were calculated by EXPLO5, as shown in Table S1 †.…”