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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2025-06-01
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| author | Moxin Sun Wenjie Xie Qi Lai Gang Zhao Ping Yin Siping Pang |
| author_facet | Moxin Sun Wenjie Xie Qi Lai Gang Zhao Ping Yin Siping Pang |
| author_sort | Moxin Sun |
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| description | 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. |
| format | Article |
| id | doaj-art-bbdbf19030f34a16b02297b452933129 |
| institution | Matheson Library |
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| language | English |
| publishDate | 2025-06-01 |
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| series | Molecules |
| spelling | doaj-art-bbdbf19030f34a16b02297b4529331292025-06-25T14:13:38ZengMDPI AGMolecules1420-30492025-06-013012258910.3390/molecules301225891,1′-(Diazene-1,2-diyl)bis(4-nitro-1H-1,2,3-triazole-5-carboxamide): An N8-Type Energetic Compound with Enhanced Molecular StabilityMoxin Sun0Wenjie Xie1Qi Lai2Gang Zhao3Ping Yin4Siping Pang5School of Materials Science and Engineering, Beijing Institute of Technology, Beijing 100081, ChinaSchool of Materials Science and Engineering, Beijing Institute of Technology, Beijing 100081, ChinaSchool of Materials Science and Engineering, Beijing Institute of Technology, Beijing 100081, ChinaSichuan Huachuan Industrial Co., Ltd., Chengdu 610106, ChinaSchool of Materials Science and Engineering, Beijing Institute of Technology, Beijing 100081, ChinaSchool of Materials Science and Engineering, Beijing Institute of Technology, Beijing 100081, ChinaThe 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.https://www.mdpi.com/1420-3049/30/12/2589long nitrogen chain compoundsnitrogen-rich heterocyclic ringazo bridgenitro-1,2,3-triazolecarboxamidelow-sensitivity energetic materials |
| spellingShingle | Moxin Sun Wenjie Xie Qi Lai Gang Zhao Ping Yin Siping Pang 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 Molecules long nitrogen chain compounds nitrogen-rich heterocyclic ring azo bridge nitro-1,2,3-triazolecarboxamide low-sensitivity energetic materials |
| title | 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 |
| title_full | 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 |
| title_fullStr | 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 |
| title_full_unstemmed | 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 |
| title_short | 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 |
| title_sort | 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 |
| topic | long nitrogen chain compounds nitrogen-rich heterocyclic ring azo bridge nitro-1,2,3-triazolecarboxamide low-sensitivity energetic materials |
| url | https://www.mdpi.com/1420-3049/30/12/2589 |
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