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 organ...
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| Main Authors: | , , , , , |
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| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2025-06-01
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| Series: | Molecules |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1420-3049/30/12/2589 |
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| Summary: | 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 KMnO<sub>4</sub>, 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<sup>−1</sup>, <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. |
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| ISSN: | 1420-3049 |