Construction of Coplanar Bicyclic Backbones for 1,2,4‐Triazole‐1,2,4‐Oxadiazole‐Derived Energetic Materials
Wenli Cao, Wen‐Shuai Dong, Zujia Lu, Yufan Bi, Yong Hu, Tingwei Wang, Chao Zhang, Zhimin Li, Qiyao Yu, Jianguo Zhang
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.