Nitration de Pyridinobenzotetraazapentalenes

Maquestiau, A.; Flammang-Barbieux, M.; Vilain, E.

doi:10.1002/bscb.19860951211

Cited by 11 publications

(1 citation statement)

References 5 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…On the basis of conjugation systems, compounds with a tetraazapentalene cyclic structure can boost their stability by constructing a unique inner-salt structure. Since BPTAP and tetranitro-dipyridotetraazapentalene (TACOT) were previously reported, worldwide researchers have also conducted a series of studies on their derivatives. − Inevitably, amino group and hydrogen-bonding interaction can decrease the sensitivity of energetic materials, which has been proved in theoretical analysis. − However, whether the introduction of amino group or hydrogen bonds affects physicochemical properties of energetic materials has not been fully addressed. In the present study, amino groups were successfully incorporated into BPTAP by molecular design and synthetic route programming.…”

Section: Introductionmentioning

confidence: 99%

Structure–Performance Relationship in Thermally Stable Energetic Materials: Tunable Physical Properties of Benzopyridotetraazapentalene by Incorporating Amino Groups, Hydrogen Bonding, and π–π Interactions

Geng

et al. 2020

Crystal Growth & Design

View full text Add to dashboard Cite

Structure−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.

show abstract