Tunable Dimroth rearrangement of versatile 1,2,3-triazoles towards high-performance energetic materials,Journal of Materials Chemistry A

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Tunable Dimroth rearrangement of versatile 1,2,3-triazoles towards high-performance energetic materials
Journal of Materials Chemistry A ( IF 10.7 ) Pub Date : 2021-4-27 , DOI: 10.1039/d1ta00109d
Shangbiao Feng _{1,

2,

3,

4,

5} , Ping Yin _{1,

2,

3,

4,

5} , Chunlin He _{1,

2,

3,

4,

5} , Siping Pang _{1,

2,

3,

4} , Jean'ne M. Shreeve _{5,

6,

7,

8}

Affiliation

A highly efficient strategy of two different types of nitrogen-rich heterocyclic energetic compounds, featuring a single NH-bridge (–NH–) and a fused ring, was demonstrated by virtue of Dimroth rearrangement reactions using 4-amino-5-nitro-1,2,3-triazole as the precursor. Various nitrogen-rich compounds and their salts were prepared via this transformation and fully characterized using multinuclear NMR spectroscopy, IR, elemental analysis, and single crystal X-ray structuring. Their key properties, such as decomposition temperatures, densities, detonation velocities and pressures, and impact sensitivities, were obtained from theoretical calculations or experimental measurements. With different task-specific explosophores, the representative energetic compounds 6b and 18 exhibit great potential as high performance insensitive energetic materials and organic primary explosives, respectively. This work gives the classic Dimroth rearrangement new vitality to access diversified task-specific energetic materials.

中文翻译：

多功能1,2,3-三唑向高性能含能材料的可调Dimroth重排

通过使用4-氨基-5-硝基-1的Dimroth重排反应证明了两种不同类型的富含氮的杂环高能化合物的高效率策略，这些化合物具有单个NH-桥（–NH–）和稠环。，2,3-三唑为前体。通过这种转化制备了各种富氮化合物及其盐，并使用多核NMR光谱，IR，元素分析和单晶X射线结构对其进行了全面表征。它们的关键特性，例如分解温度，密度，爆震速度和爆破压力以及冲击敏感度，是通过理论计算或实验测量获得的。具有不同的任务特定的炸药，典型的高能化合物6b和18分别作为高性能不敏感的高能材料和有机主要炸药具有巨大的潜力。这项工作为经典的Dimroth重排赋予了新的活力，使他们可以访问各种任务特定的精力充沛的材料。

更新日期：2021-05-17

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