Synthesis of Ideal Energetic Materials with High Density and Performance Based on 5-Aminotetrazole

Lei, Caijin; Yang, Hongwei; Yang, Wei; Zhang, Qinghua

doi:10.1021/acs.cgd.2c00058

Cited by 26 publications

(28 citation statements)

References 34 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Compound 2 exhibits an intense face-toface stacking arrangement, and its interlayer distance is 3.256 Å, shorter than the typical geometrical parameters of aromatic π−π interactions (3.300−3.600 Å). 15 3e). Compound 7 also exhibits a cage-stacking 3D framework arrangement (Figure 3f).…”

Section: Resultsmentioning

confidence: 97%

See 1 more Smart Citation

Series of Azido and Fused-Tetrazole Explosives: Combining Good Thermal Stability and Low Sensitivity

Lei

Yang

Zhang

2022

ACS Appl. Mater. Interfaces

Self Cite

View full text Add to dashboard Cite

The introduction of azido groups into the energetic skeleton has the advantages of increasing the energy level. In this work, a series of azido compounds with good stability and low sensitivity as well as tetrazole-fused compounds based on energetic salts are synthesized. The detonation pressures and velocities of these new compounds fall in the ranges of 18.9–27.3 GPa and 7153–8450 m s–1, respectively. The detonation velocity of the tetrazole-fused compounds based on the potassium salts 3, 6, and 7 are 7810, 7153, and 7989 m s–1, respectively. Also, their decomposition temperatures (244, 237, and 240 °C, respectively) are higher than that of traditional explosive RDX (204 °C). Notably, two representative compounds 2 and 5 possess higher decomposition temperature (2: 196 °C and 5: 178 °C) and overall detonation properties (2: D = 8129 m s–1 and P = 26.6 GPa and 5: D = 8336 m s–1 and P = 27.3 GPa) as well as relativity lower sensitivities (2: IS = 12 J and FS = 240 N and 5: IS = 10 J and FS = 144 N) than that of primary explosive 2-diazo-4,6-dinitrophenol (T d = 157 °C, D = 6900 m s–1, P = 24.7 GPa, IS = 1 J, and FS = 24.7 N). Moreover, the initiation capacity of compounds 2 and 5 was also assessed through the initiation tests. The results indicate that the two compounds could be a promising environmentally friendly primary explosive.

show abstract

Section: Resultsmentioning

confidence: 97%

“…The crystal packing of 2 is shown in Figure d. Compound 2 exhibits an intense face-to-face stacking arrangement, and its interlayer distance is 3.256 Å, shorter than the typical geometrical parameters of aromatic π–π interactions (3.300–3.600 Å) …”

Section: Resultsmentioning

confidence: 99%

Series of Azido and Fused-Tetrazole Explosives: Combining Good Thermal Stability and Low Sensitivity

Lei

Yang

Zhang

2022

ACS Appl. Mater. Interfaces

Self Cite

View full text Add to dashboard Cite

show abstract

“…Considering tetrazole, as an excellent energetic block with high stability and high enthalpy, can be used to strengthen the hydrogen bonding interactions, − here, we incorporated the tetrazole group into the DNII structure to improve the molecular stability and energy. As shown in Scheme , the tetrazole groups were linked to the DNII system through an ethylene bridge ( 3 ), a methylene bridge ( 5 ), and direct connection ( 6 ).…”

Section: Introductionmentioning

confidence: 99%

High-Energy and Insensitive Tetrazole-Substituted 2,5-Dinitroiminooctahydroimidazo[4,5-d]imidazole: Synthesis, Characterization, and Energetic Properties

Liu

Gao

Xing

et al. 2022

Crystal Growth & Design

View full text Add to dashboard Cite

Herein, we present the synthesis and characterization of three novel energetic compounds based on 2,5dinitroiminooctahydroimidazo [4,5-d]imidazole (DNII). The tetrazole groups were linked to DNII through an ethylene bridge (3), a methylene bridge (5), or direct connection (6). These compounds were fully characterized and their detonation properties were well determined by quantum chemical calculations. Among them, compound 5 exhibited two crystal forms (U-5 and T-5) in methanol and water. Compared to U-5, T-5 increased in density, formation enthalpy, detonation velocity, and pressure by 0.04 g/cm 3 (2.3%), 0.22 kJ/g (8.1%), 0.34 km/s (4.2%), and 2.6 GPa (10.8%), respectively, owing to the tighter packing model. More importantly, with the gradual shortening of the linkages between imidazole and tetrazole, the performance of these compounds was gradually improved. Moreover, compound 6 showed the best detonation properties (D = 9.08 km/s, P = 33.1 GPa), which was better than TNT and close to HMX, while its sensitivity toward external forces (impact sensitivity (IS) = 40 J, friction sensitivity (FS) = 360 N) was much lower, making it safer. This work aims to prepare high-energy, low-sensitivity materials and hope to be helpful for the development of future energetic materials.

show abstract

“…25 Introduction of an explosophoric group (-NHNO 2 ) into the molecule results in the enhanced density of the energetic compounds with a simultaneous increase in sensitivity. 26 However, proton acceptor explosophoric groups such as nitro and nitramino groups and hydrogen bond donors like amino groups and N−H bonds participate in strong intramolecular hydrogen bonding interactions; in this way, it is a promising strategy for synthesizing insensitive HEDMs. Various fused heterocyclic HEDMs have also been reported, but the low molecular stability limits their practical use.…”

mentioning

confidence: 99%

“…Also, the -NH- bridges in energetic materials have the advantage of intra- and intermolecular H-bonding, which lowers their sensitivity. , The establishment of such a motif by employing a transition metal via cross-coupling is not a satisfactory method for accessing nitrogen-rich heterocycles due to catalyst poisoning . Introduction of an explosophoric group (-NHNO 2 ) into the molecule results in the enhanced density of the energetic compounds with a simultaneous increase in sensitivity . However, proton acceptor explosophoric groups such as nitro and nitramino groups and hydrogen bond donors like amino groups and N–H bonds participate in strong intramolecular hydrogen bonding interactions; in this way, it is a promising strategy for synthesizing insensitive HEDMs.…”

mentioning

confidence: 99%

1,3,5-Tris[(2H-tetrazol-5-yl)methyl]isocyanurate and Its Tricationic Salts as Thermostable and Insensitive Energetic Materials

2022

View full text Add to dashboard Cite

Various energetic salts (3a–f) were obtained from 1,3,5-tris[(2H-tetrazol-5-yl)methyl]isocyanurate (3), while N2,N4,N6-tri(1H-tetrazol-5-yl)-1,3,5-triazine-2,4,6-triamine (5) and N,N′-{6-[(1H-tetrazol-5-yl)amino]-1,3,5-triazine-2,4-diyl}bis[N-(1H-tetrazol-5-yl)nitramide] (6) were obtained from cyanuric chloride via a simple, efficient two-step synthetic route from inexpensive starting materials. Compounds 3a–f and 6 show excellent detonation properties (VOD = 7876–8832 m s–1, and DP = 20.73–30.0 GPa), a high nitrogen content (>62%), and high positive heats of formation (205.2–1888.9 kJ mol–1) with excellent thermostability and remarkable insensitivity.

show abstract

Synthesis of Ideal Energetic Materials with High Density and Performance Based on 5-Aminotetrazole

Cited by 26 publications

References 34 publications

Series of Azido and Fused-Tetrazole Explosives: Combining Good Thermal Stability and Low Sensitivity

Series of Azido and Fused-Tetrazole Explosives: Combining Good Thermal Stability and Low Sensitivity

High-Energy and Insensitive Tetrazole-Substituted 2,5-Dinitroiminooctahydroimidazo[4,5-d]imidazole: Synthesis, Characterization, and Energetic Properties

1,3,5-Tris[(2H-tetrazol-5-yl)methyl]isocyanurate and Its Tricationic Salts as Thermostable and Insensitive Energetic Materials

Contact Info

Product

Resources

About