Synthesis of energetic salts containing three heterocyclic anions by a one-pot condensation reaction

Peng, Panpan; Hu, Baoping; Lu, Feipeng; Du, Yao; Zhao, Chaofeng; Su, Hui; Zhang, Pengcheng; Li, Sheng‐Hua; Pang, Siping

doi:10.1039/c9nj03857d

Cited by 4 publications

(1 citation statement)

References 37 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…and physical modification (blending, porous material coating, etc. ), − which require multistep operations and sometimes introduce new problems, such as moisture absorption and caking of ammonium salt under natural conditions. More importantly, the unstable all-carbon-nitrated azoles may have the potential danger of explosion during operation.…”

Section: Introductionmentioning

confidence: 99%

Improving the Stability of All-Carbon-Nitrated Azoles through Cocrystallization

Peng

Ding

Zhao

et al. 2022

Crystal Growth & Design

Self Cite

View full text Add to dashboard Cite

All-carbon-nitrated azoles have the advantages of high density and good oxygen balance, but they are rarely suitable for explosives applications due to their fatal deficiencies, such as poor thermal stability, sensitivity, and deliquescence. Cocrystallization technology provides a feasible idea to revive all-carbon-nitrated azoles in the presence of flexible structure designability and performance adjustability. In this study, three attractive energetic cocrystals 1−3 were synthesized with conjugate structure triimidazo[1,2-a:1′,2′-c:1″,2″-e][1,3,5]triazine (TT) and another all-carbon-nitrated azole [5-nitrotetrazole (HNT), 3,5-dinitro-1,2,4triazole (HDNT), and 3,4,5-trinitropyrazole (TNP)], respectively. All the cocrystals 1−3 existed stably and safely under natural conditions and exhibited better thermal stability, frictional sensitivity (FS), and impact sensitivity (IS) than pure HNT, HDNT, and TNP. Therein, two melting points (T m ) of 2 were 61.9 and 95.5 °C higher than that of HDNT, and its decomposition temperature (T d ) was 81.2 °C higher than that of HDNT. The mechanical sensitivity of 1 (FS = 80 N and IS = 24 J) was significantly improved compared with the extremely sensitive HNT (FS < 5 N and IS < 1 J). Moreover, 3 exhibited excellent controllable detonation performances (1.703 g cm −3 , 6903 m s −1 , and 18.0 GPa), which was better than 2,4,6-trinitrotoluene. The single-crystal structure analysis and theoretical calculation analysis showed that the formation of three cocrystals primarily depended on N−H•••N, C−H••• N, and C−H•••O hydrogen bonds and NO 2 •••π interaction with a π−π stacking. The thermal stability and sensitivity of 1−3 were obviously better than that of pure energetics, which was attributed to the combination of these strong hydrogen bond interactions and weak NO 2 •••π and π-stacking interactions. Therefore, the cocrystallization technology provides a promising method to give these "dead" all-carbon-nitrated azoles a new life.

show abstract