Two series of [1,2,4]triazolo[4,3-b][1,2,4,5]tetrazine-based energetic materials were synthesized effectively by using monosubstituted tetrazine or tetrazine-based fused rings as starting materials. Among them, compound 5 exhibits excellent insensitivity toward external stimuli (IS = 43 J and FS > 360 N) and a very good calculated detonation performance (D_v = 9408 m s⁻¹ and P = 37.8 GPa) that are comparable to the current secondary-explosive benchmark, CL-20, which strongly suggests 5 as a secondary explosive. The azo compound 10 has a remarkable measured density of 1.91 g cm⁻³ at 20 °C, excellent thermal stability (T_d = 305 °C), and very good calculated detonation performance (D_v = 9200 m s⁻¹ and P = 34.8 GPa), which outperforms all current heat-resistant explosives. Compound 10 has a significant potential as a heat-resistant explosive. Compounds 14, 17 and 19 are very sensitive (IS ≤ 2 J and FS ≤ 100 J) but exhibit excellent calculated detonation performance (D_v ≥ 8690 m s⁻¹ and P ≥ 30.2 GPa) which are very high values among current azide-containing primary explosives. These attractive features suggest strong possibilities for applications as primary explosives. A detailed study based on X-ray diffraction is used to illustrate the relationship between weak interactions and sensitivity of energetic materials. Attempts were made to design next-generation fused ring energetic materials for different applications as an alternating kind or site of the substituent group(s).

中文翻译：

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多用途[1,2,4]三唑并[4,3- b ] [1,2,4,5]基于四嗪的高能材料†

以单取代的四嗪或基于四嗪的稠环为起始原料，有效地合成了两类[1,2,4]三唑并[4,3- b ] [1,2,4,5]四嗪系含能材料。其中，化合物5对外部刺激表现出优异的不敏感性（IS = 43 J，FS> 360 N），并且具有非常好的计算出的爆震性能（D _v = 9408 ms ^-1和P = 37.8 GPa），与目前的次级炸药相当。 -爆炸基准CL-20，强烈建议5为二次爆炸物。偶氮化合物10在20°C下的测量密度为1.91 g cm ^-3，具有出色的热稳定性（T _d = 305°C），并且具有非常好的计算爆炸性能（D _v = 9200 ms ^-1和P = 34.8 GPa），其性能优于所有目前的耐热炸药。化合物10具有作为耐热炸药的巨大潜力。化合物14，17和19是非常敏感的（IS≤2 J和FS≤100 J），但表现出优良的爆轰计算性能（d _v ≥8690毫秒^-1和P≥30.2 GPa），这是目前含叠氮化物的初级炸药中非常高的值。这些引人入胜的特征表明其有可能用作主要炸药。基于X射线衍射的详细研究用于说明弱相互作用与高能材料的敏感性之间的关系。尝试设计用于不同应用的下一代稠环含能材料，作为取代基的交替种类或位点。