Energetic derivatives substituted with trinitrophenyl: improving the sensitivity of explosives

The incorporation of trinitrophenyl-modified 1,3,4-oxadiazole fragments is commonly observed in high-energy molecules with heat-resistant properties. This study explores the strategy of developing heat-resistant energetic materials by incorporating trinitrophenyl and an azo group into 1,3,4-oxadiazo...

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Published in:Dalton transactions : an international journal of inorganic chemistry 2024-11, Vol.53 (46), p.18467-18472
Main Authors: Yu, Qiong, Chen, Yu-cong, Guo, Zihao, Li, Tao, Liu, Zunqi, Yi, Wenbin, Staples, Richard J, Shreeve, Jean'ne M
Format: Article
Language:English
Subjects:
Chemical analysis
Chemical compounds
Chemical synthesis
Energetic materials
Heat resistant materials
NMR
Nuclear magnetic resonance
Oxadiazoles
Single crystals
Thermal stability
X ray analysis
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Summary:The incorporation of trinitrophenyl-modified 1,3,4-oxadiazole fragments is commonly observed in high-energy molecules with heat-resistant properties. This study explores the strategy of developing heat-resistant energetic materials by incorporating trinitrophenyl and an azo group into 1,3,4-oxadiazole, which involved the synthesis and characterization of ( E )-1,2-bis(5-(2,4,6-trinitrophenyl)-1,3,4-oxadiazol-2-yl)diazene ( 2 ), N -(5-(2,4,6-trinitrophenyl)-1,3,4-oxadiazol-2-yl)nitramide ( 3 ), and the energetic salts of 3 . Characterization techniques employed included 1 H and 13 C NMR, IR and elemental analysis. Additionally, the structures of 2 and 3 were validated using single crystal X-ray analysis. To further understand the physical and chemical characteristics of these novel energetic compounds, various calculations and measurements were performed. Compound 2 exhibits excellent thermostability ( T d = 294 °C), which is comparable to that of traditional heat-resistant explosive HNS ( T d = 318 °C). But 2 is insensitive towards impact (>40 J) and friction (>360 N), surpassing HNS (5 J, 240 N), suggesting that compound 2 deserves further investigation as a potential heat-resistant explosive. Excellent mechanical sensitivity: incorporating trinitrophenyl into azo-1,3,4-oxadiazole compounds results in a heat-resistant explosive with excellent impact and friction sensitivity, along with good thermal stability.
ISSN:1477-9226
1477-9234
1477-9234
DOI:10.1039/d4dt02070g