1,1′-(Diazene-1,2-diyl)bis(4-nitro-1H-1,2,3-triazole-5-carboxamide): An N8-Type Energetic Compound with Enhanced Molecular Stability

The safety concerns associated with sensitivity issues regarding long nitrogen chain-based energetic compounds, especially for eight or more catenated nitrogen atoms in backbones, need to be resolved. Incorporating specific functional groups represents a key approach for enhancing stability in organic energetic materials. This study reports the synthesis of 1,1'-(diazene-1,2-diyl)bis(4-nitro-1H-1,2,3-triazole-5-carboxamide) (<b>S8</b>), an N8-chain compound featuring strategically placed amide groups. Employing THA(<i>O</i>-tosylhydroxylamine) and KMnO₄, 1,1'-(diazene-1,2-diyl)bis(4-nitro-1H-1,2,3-triazole-5-carboxamide) (<b>S8</b>) was synthesized and underwent N-amination and oxidative azo coupling. Comprehensive characterization, including X-ray diffraction, mechanical sensitivity testing, and theoretical analysis, alongside comparative studies with known N8 compounds, revealed that S8 exhibits unprecedented stability within its class. Among reported N8-catenated nitrogen chain compounds, attributed to the incorporation of the amide functionality, <b>S8</b> demonstrates the highest impact sensitivity (IS = 10 J) and friction sensitivity (FS = 40 N) while maintaining excellent detonation performance (<i>D</i> = 8317 ms^-1, <i>P</i> = 28.27 GPa). This work highlights the amide group as a critical structural part for achieving high stability in sensitive long-nitrogen-chain energetic materials without compromising performance.