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Structure–Performance Relationship in Thermally Stable Energetic Materials: Tunable Physical Properties of Benzopyridotetraazapentalene by Incorporating Amino Groups, Hydrogen Bonding, and π–π Interactions
journal contribution
posted on 2020-02-21, 17:41 authored by Wen-Jing Geng, Qing Ma, Ya Chen, Wei Yang, Yun-Fei Jia, Jin-Shan Li, Zhen-Qi Zhang, Gui-Juan Fan, Shu-Min WangStructure–performance
investigation has become one of those
significant trends for energetic materials and energetic crystallography
inevitably. Herein, we report two new energetic materials deriving
from a famous thermally stable explosive benzopyridotetraazapentalene,
which was first developed by Huynh and Hiskey, et al., at Los Alamos
National Laboratory. Owing to the incorporation of amino groups, these
two energetic materials exhibit different amusing physical performance.
Understanding their structures, properties, performances, and the
relationship among them is the basis for the rational design of thermally
stable energetic materials. Moreover, for these energetic conjugated
systems, the density overlap regions indicator analysis was also employed
for necessarily visualizing and quantifying the covalent and noncovalent
interactions. It is evident that this strategy of incorporating amino
groups into energetic materials increased the coplanarity of the energetic
fused ring, owing to the contribution of hydrogen bonding and π–π
interactions, which can further decrease their sensitivity. However,
we also found that the integrity of intramolecular hydrogen -bonding
interaction was the critical factor, which affected the thermal stability
of energetic molecules with the amino groups inserting progressively.
It is notable that diamino-substituted energetic compound 8 exhibits comparable thermal stability (320 °C) to that of HNS,
more dense (d: 1.84 g cm–3), higher
nitrogen content (37.43%), and lower sensitivity (impact sensitivity:
12 J, friction sensitivity > 360 N), superior to those of HNS.
These
discoveries can effectively assist the design and preparation of other
promising thermally stable energetic materials toward future high-performing
energy applications.
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friction sensitivityenergy applicationsintramolecular hydrogennoncovalent interactionsimpact sensitivityTunable Physical PropertiesThermally StableHNSLos Alamos National Laboratorymaterials exhibitcompound 8 exhibitsHydrogen Bonding12 JIncorporating Amino Groupsdensity overlap regions indicator analysis
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