Very thermostable energetic materials based on a fused-triazole: 3,6-diamino-1<i>H</i>-[1,2,4]triazolo[4,3-<i>b</i>][1,2,4]triazole

Tang, Yongxing; An, Ziwei; Chinnam, Ajay Kumar; Staples, Richard J.; Shreeve, Jean’ne M.

doi:10.1039/d0nj05152g

Cited by 25 publications

(9 citation statements)

References 27 publications

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“…To investigate this question, the best research subjects are isomers as they have an identical elemental composition. − Previous studies have shown that arrangement of amino groups in isomers has significant impact on physicochemical properties; for example, 3,5-dinitro-4-aminopyrazole (LLM-116) and 5-amino-3,4-dinitropyrazole (5-ADP) (Figure a) exhibit comparable detonation performance. , However, LLM-116 has lower thermal stability but higher insensitivities relative to 5-ADP. A similar phenomenon was also observed in energetic isomers based on the 1 H -[1,2,4]triazolo[4,3- b ][1,2,4]triazole skeleton (Figure b) . DATT-1 with amino groups located on two carbon sites shows superior thermal stability but lower detonation performance compared to its analogue DATT-2.…”

Section: Introductionmentioning

confidence: 99%

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Toward Advanced High-Performance Insensitive FOX-7-like Energetic Materials via Positional Isomerization

Yin

Huang

Zeng

et al. 2022

ACS Appl. Mater. Interfaces

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For an energetic molecule with a definite elemental composition, the substituent type and position are the most important factors to influence its detonation performance and mechanical sensitivities. In this work, two pairs of FOX-7-like energetic isomers based on (2 and HTz-FOX; 5 and 6) were synthesized and characterized. Through positional isomerization, advanced high-performance insensitive explosives were obtained. Compounds 2 and 5 with an amino group adjacent to the electron-withdrawing side of the ethene bridge show both higher thermal stability and lower mechanical sensitivities (2: T d = 258 °C, impact sensitivity (IS) = 25 J, and friction sensitivity (FS) = 300 N; 5: T d = 264 °C, IS = 30 J, and FS = 320 N). In addition, 2 shows ultrahigh detonation performance (D v = 9224 m s–1 and P = 31.1 GPa). These promising physicochemical properties are comparable to those of HMX (D v = 9193 m s–1, P = 37.8 GPa, T d = 275 °C, IS = 7.4 J, and FS = 120 N), which suggests that 2 may be a promising energetic material in future applications.

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Section: Introductionmentioning

confidence: 99%

“…A similar phenomenon was also observed in energetic isomers based on the 1H- [1,2,4]triazolo [4,3-b] [1,2,4]triazole skeleton (Figure 1b). 26 DATT-1 with amino groups located on two carbon sites shows superior thermal stability but lower detonation performance compared to its analogue DATT-2.…”

Section: ■ Introductionmentioning

confidence: 99%

Toward Advanced High-Performance Insensitive FOX-7-like Energetic Materials via Positional Isomerization

Yin

Huang

Zeng

et al. 2022

ACS Appl. Mater. Interfaces

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“…Because the synthesized energetic salts have a high nitrogen content, several representatives, namely salts 5c and 6 , were additionally characterized by 15 N NMR spectroscopy ( Figure 2 ). The signals were assigned by comparison with similar structures ( Thottempudi and Shreeve, 2011 ; Tang et al, 2021 ). There are thirteen signals in the 15 N NMR spectrum of 5c .…”

Section: Resultsmentioning

confidence: 99%

Novel family of nitrogen-rich energetic (1,2,4-triazolyl) furoxan salts with balanced performance

et al. 2022

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Nitrogen-rich energetic materials comprised of a combination of several heterocyclic subunits retain their leading position in the field of materials science. In this regard, a preparation of novel high-energy materials with balanced set of physicochemical properties is highly desired. Herein, we report the synthesis of a new series of energetic salts incorporating a (1,2,4-triazolyl) furoxan core and complete evaluation of their energetic properties. All target energetic materials were well characterized with IR and multinuclear NMR spectroscopy and elemental analysis, while compound 6 was further characterized by single-crystal X-ray diffraction study. Prepared nitrogen-rich salts have high thermal stability (up to 232°C), good experimental densities (up to 1.80 g cm−3) and high positive enthalpies of formation (344–1,095 kJ mol−1). As a result, synthesized energetic salts have good detonation performance (D = 7.0–8.4 km s−1; p = 22–32 GPa), while their sensitivities to impact and friction are quite low.

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“…The 15 N NMR spectra were recorded for 3 , 4 , 5a , and 7e in DMSO- d 6 , and the assignments were made by comparison with similar compounds (Figure S23). , …”

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confidence: 84%

“…The 15 N NMR spectra were recorded for 3, 4, 5a, and 7e in DMSO-d 6 , and the assignments were made by comparison with similar compounds (Figure S23). 20,21 Single yellow block crystals of 4 and single yellow needle crystals of 5b were obtained by slow evaporation of EtOH/ water solutions (Figure 2). Compound 4 crystallizes in the monoclinic space group P2 1 /n (Z = 4) symmetry with a calculated density of 1.879 g•cm −3 at 100 K. The bond lengths and bond angles are slightly different from the reported structure.…”

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Nucleophilic Catalyzed Structural Binary Cleavage of a Fused [5,5]-Bicyclic Compound

2021

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Structural binary cleavage of 3,7-diamino-2,6dinitro-1H,5H-pyrazolo-[1,2-a]pyrazole-1,5-dione 3, under nucleophilic conditions, leads to the formation of a monocyclic pyrazole unit of 5-amino-4-nitro-1,2-dihydro-3H-pyrazol-3-one, 4. Additionally, various salts of the pyrazole ring were synthesized and fully characterized. Detonation properties and mechanical sensitivities of 4 and other new compounds are remarkably improved compared to 3. This simple and efficient strategy is highly desirable for future studies on the development of insensitive and high performing materials.

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Very thermostable energetic materials based on a fused-triazole: 3,6-diamino-1H-[1,2,4]triazolo[4,3-b][1,2,4]triazole

Abstract: 3,6-Diamino-1H-[1,2,4]triazolo[4,3-b][1,2,4]triazole (1) and its energetic salts (2-9) were designed and synthesized based on a fused-triazole backbone with two C-amino groups as substituents. Their physicochemical and energetic properties were measured or...

Cited by 25 publications

References 27 publications

Toward Advanced High-Performance Insensitive FOX-7-like Energetic Materials via Positional Isomerization

Toward Advanced High-Performance Insensitive FOX-7-like Energetic Materials via Positional Isomerization

Novel family of nitrogen-rich energetic (1,2,4-triazolyl) furoxan salts with balanced performance

Nucleophilic Catalyzed Structural Binary Cleavage of a Fused [5,5]-Bicyclic Compound

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