A Family of Energetic Materials Based on 1,2,4-Oxadiazole and 1,2,5-Oxadiazole Backbones With Low Insensitivity and Good Detonation Performance
Qi Xue, Fuqiang Bi, Jun-Lin Zhang, Zijun Wang, Lianjie Zhai, Huan Huo, Bozhou Wang, Shengyong Zhang
Abstract
Design and synthesis of new compounds with both high detonation performances and good safety properties have always been a formidable task in the field of energetic materials. By introducing -ONO2, -NHNO2 moieties into 1,2,4-oxadiazole- and 1,2,5-oxadiazole-based backbones, a new family of energetic materials, including ammonium 3-nitramino-4-(5-hydroxymethyl-1,2,4-oxadiazol-3-yl)-furazan (4), 3,3'-bis[5-nitroxymethyl-1,2,4-oxadiazol-3-yl]-4,4'-azofuroxan (6), [3-(4-nitroamino-1,2,5-oxadiazol-3-yl)-1,2,4-oxadiazol-5-yl]-methylene nitrate (8) and its energetic ionic salts (10-12), were synthesized and fully characterized. The energetic and physical properties of the materials were investigated through theoretical calculations and experimental determination.The results show that the oxadiazole-based compounds exhibit high enthalpy of formations, good detonation performances and extraordinary insensitivities. In particular, the hydrazinium salt (11) shows the best energetic properties (11: d =1.821 g cm-3; P = 35.1 GPa, vD = 8822 m s-1, IS = 40 J, FS > 360 N). The ESP and Hirshfeld surfaces analysis indicated that a large number of hydrogen bonds as well as π-π stacking interacions within molecules might be the key reason for their low sensitivities and high energy-density levels