Benzofuroxan‐Based Energetic Materials with Alternating Nitro and Hydroxyl Groups: Synthesis, Characterization, and Energetic Properties DOI Open Access

Atharva Tiwari,

Krishna Pandey, Priyanka Das

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 9, 2024

Abstract Due to its good stability, density and oxygen balance, the benzofuroxan fused ring framework has attracted particular attention in field of high energy materials. The planar structure facilitates straightforward derivatization with explosophores contributes molecular stability. In this work, a scaffold was utilized develop highly dense energetic material, namely 5,7‐dihydroxy‐4,6‐dinitrobenzo[c][1,2,5]oxadiazole 1‐oxide ( DHDNBF ). successive inclusion like nitro (−NO 2 ) oxidative functionality hydroxyl (−OH) on resulted an impressive (ρ=1.91 g cm −3 positive balance (6.20 %) Furthermore, hydroxy groups enable formation dicationic salts 3 – 7 , contributing additional modifications overall performance. Energetic 4 5 exhibit significantly higher densities ranging from 1.84 1.87 possess favorable approaching zero or equal zero. A marked improvement thermal stabilities observed all compared their neutral counterparts, . (D v =8459 m s −1 P=32.10 GPa) =8539 P=30.37 performance, comparable that well‐known explosives such as LLM‐105 =8560 P=33.4 GPa). Overall, characteristics make them potential candidates for use benzofuroxan‐based secondary primary explosives, respectively, various military civilian applications.

Language: Английский

Insights into Structural and Energetic Features of 3,5-Dinitropyrazole-4-carboxylic Acid and Its Energetic Salts DOI
Krishna Pandey, Priyanka Das, Prachi Bhatia

et al.

Crystal Growth & Design, Journal Year: 2024, Volume and Issue: 24(16), P. 6790 - 6799

Published: July 31, 2024

The dominance of nitro pyrazole-based explosives in the recently reported high-performing energetic materials motivated us to comprehensively investigate energy–stability correlation among different compounds based on 3,5-dinitro pyrazoles employing various computational methods. We also explored and physicochemical properties overlooked compound 3,5-dinitropyrazole-4-carboxylic acid (CDNP). This study revealed that CDNP exhibits highest thermal stability 4-substituted-3,5-dinitropyrazoles, combined with an acceptable performance. These characteristics are attributed its layered packing, strong intermolecular interactions, carbonyl bonds. Furthermore, dicationic salt formation further allowed fine-tune overall performance stability. dihydroxylammonium (5) shows best performance, comparable well-known traditional explosive TATB, good low sensitivity toward impact friction.

Language: Английский

Citations

8
N-Methylene-C-Linked Nitropyrazoles and 1,2,4-Triazolone-3-one: Thermally Stable Energetic Materials with Reduced Sensitivity DOI
Krishna Pandey, Priyanka Das,

Meera Khatri

et al.

Dalton Transactions, Journal Year: 2024, Volume and Issue: 53(42), P. 17179 - 17189

Published: Jan. 1, 2024

A family of new asymmetric N -methylene-C linked nitropyrazoles and 1,2,4-triazol-3-one based thermally stable energetic materials with reduced sensitivity has been synthesized. Background image via Canva.

Language: Английский

Citations

4
Intramolecular Cyclization and Energetic Group Modifications for Thermally Stable and Low-Sensitivity Monocyclic Dinitromethyl Zwitterionic Pyrazoles DOI
Changlin Zhou,

Qingshan Xie,

Junqi Wang

et al.

Inorganic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 13, 2025

Zwitterionic energetic materials offer a unique combination of high performance and stability, yet their synthesis stability enhancement remain key challenges. In this study, we report the highly stable (dinitromethyl-functionalized zwitterionic compound, 1-(amino(iminio)methyl)-4,5-dihydro-1H-pyrazol-5-yl)dinitromethanide (4), with thermal decomposition temperature 215 °C, surpassing that most previously reported monocyclic zwitterions (Td < 150 °C). This compound was synthesized via intramolecular cyclization trinitromethyl-functionalized hydrazone precursor. Further chemical modifications, including nitration fluorination, enabled zwitterion-to-zwitterion transformations, resulting in formation nitramines 10 12. Additionally, perchlorate salt (8) 4 synthesized, along ammonium (13), guanidinium (14), potassium (15) salts derived from 10, all retaining properties. Physicochemical evaluations reveal zwitterion 12 exhibits excellent = 181 °C) an optimal balance between energy output (detonation velocity: 8329 m s-1, detonation pressure: 29.4 GPa) reduced sensitivity (impact sensitivity: 35 J, friction 320 N). Notably, 15 demonstrates superior 233 °C), exceeding RDX. These results expand design framework for contribute to development high-energy, low-sensitivity materials.

Language: Английский

Citations

0
Comparative Study of Trifunctionalization for Enhanced Energy and Thermal Stability in Zwitterionic Fused Triazole Skeletons DOI
Zhe Wang, Hui Zhang, Yin Xia

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: 27(4), P. 1060 - 1065

Published: Jan. 16, 2025

In this work, two energetic compounds 5-(3-iminio-6-nitro-3H-[1,2,4]triazolo[4,3-b][1,2,4]triazol-2(7H)-yl)tetrazol-1-ide (TT) and 3-nitro-7-(2H-tetrazol-5-yl)-7H-[1,2,4]triazolo[4,3-b][1,2,4]triazol-6-amine (FT) were successfully synthesized from the same compound 3,6,7-triamino-7H-[1,2,4]triazolo[4,3-b][1,2,4]triazolium (TATOT). Both contain three explosophores, amino, nitro, tetrazole, on fused ring. Through different functional group arrangements, TT possesses higher density good thermal stability. FT exhibits a low sensitivity to mechanical stimulation. show promising performance properties.

Language: Английский

Citations

0
The Effect of Metal-Doped ZIF-67 on the Thermal Decomposition of Nitrocellulose DOI
Jiang Ju, Zhitao Liu, Hao Guo

et al.

Catalysis Letters, Journal Year: 2025, Volume and Issue: 155(3)

Published: Jan. 22, 2025

Language: Английский

Citations

0
Zwitterionic energetic materials containing an oxatriazole explosophore: an exploration of structure and performance DOI
Congming Ma, Zhihui Gu, Jiani Xu

et al.

Structural Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 23, 2025

Language: Английский

Citations

0
New Zwitterionic Compounds Based on 1-(tetrazol-5-yl)-1,2,4-triazole: High-Energy, Low-Sensitivity Energetic Materials DOI

Fubing Yang,

Chengming Bian,

Ximei Yang

et al.

Journal of Molecular Structure, Journal Year: 2025, Volume and Issue: unknown, P. 141579 - 141579

Published: Jan. 1, 2025

Language: Английский

Citations

0
N‐Alkylation of 4‐Hydroxy‐3,5‐Dinitropyrazole: A Facile Route for the Synthesis of Insensitive Energetic Materials DOI Open Access
Prachi Bhatia, Priyanka Das, Dheeraj Kumar

et al.

Propellants Explosives Pyrotechnics, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 4, 2025

ABSTRACT Behind the synthesis of any new high‐energy density material is objective to achieve equilibrium between energy and stability, which becomes laborious because their adversarial nature. Nitropyrazoles, with viable syntheses easy modifiability, have been adopted typically as backbones this goal. However, acidic nature pyrazole N H in nitropyrazoles limits usefulness despite exhibiting appealing characteristics. 4‐Hydroxy‐3,5‐dinitropyrazole (HODNP) an interesting skeleton presence hydroxy functionality two nitro groups, not only provides additional oxygen content for better output but also possesses quality strong hydrogen bonding interactions tuning properties via salt formation. N‐alkylation most straightforward technique protection unwanted proton, addition making them more physically stable. In work, we synthesized ‐methylated , N’ ‐ethylene‐bridged derivatives ( 2 7 ) HODNP. Mono dicationic salts 3 ‐ 6 8 11 were boost performance further. N‐methylated neutral compound its ammonium confirmed through 15 NMR analysis, was single‐crystal analysis. All compounds showed excellent physical stability (IS >40 J, FS > 360 N), good thermal (T d 180°C). The detonation characteristics found be similar ones 1,3,5‐triamino‐2,4,6‐trinitrobenzene (D v = 7704–8172 m/s, p 22.4–27.3 GPa).

Language: Английский

Citations

0
Synthesis and Properties of Trinitromethyl‐1H‐1,2,4‐Triazole Bridging Nitropyrazole Energetic Salts DOI
Lihua Xie,

Pingping Yi,

Chenchen Lin

et al.

ChemistrySelect, Journal Year: 2025, Volume and Issue: 10(18)

Published: May 1, 2025

Abstract The polynitroazole plays an important role in the design of high‐energy density materials. A series nitrogen‐rich salts based on trinitromethyl‐substituted 1 H ‐1,2,4‐triazole bridging nitropyrazole was prepared. These newly synthesized were fully characterized by chemical analysis (infrared, NMR, and mass spectroscopy) as well experimental tests (thermostability sensitivities). Their detonation properties (detonation velocity, pressure, etc.) determined EXPLO5 program basis heat formation. show moderate thermostabilities low sensitivities (IS ≥ 10 J, FS 252 N) due to intermolecular hydrogen bonding interactions. most promising insensitive compound is salt 2, which possesses a high (1.80 g cm −3 ), relatively thermal stability (149 °C), sensitivity = 30 N), good velocity (8997 m s −1 ) pressure (36.7 GPa) comparable cyclotrimethylenetrinitramine (RDX). This study supports efficiency utilizing combined with systems development new high‐energy, energetic

Language: Английский

Citations

0
Engaging Two Anions with Single Cation in Energetic Salts: Approach for Optimization of Oxygen Balance in Energetic Materials DOI
Prachi Bhatia, Priyanka Das, Dheeraj Kumar

et al.

ACS Applied Materials & Interfaces, Journal Year: 2024, Volume and Issue: 16(47), P. 64846 - 64857

Published: Nov. 12, 2024

The field of high energy density materials faces a long-standing challenge to achieve an optimum balance between and stability. While energetic salt formation via combination oxygen- nitrogen-rich anions (providing energy) with nitrogen-containing cations stability) has been proven approach for improving physical stability, constraints such as lowering performance remain unresolved. This can be addressed by utilizing oxygen-containing formation. However, this is rarely explored because its synthesis challenging. In work, we have designed oxygen-rich cationic precursor

Language: Английский

Citations

2