Zwitterionic Energetic Materials: Synthesis, Structural Diversity and Energetic Properties

Chemistry - An Asian Journal, Год журнала: 2024, Номер 19(17)

Опубликована: Июнь 10, 2024

Abstract Zwitterionic compounds are an emergent class of energetic materials and have gained synthetic interest many in the recent years. Due to their better packing efficiencies strong inter/intramolecular electrostatic interactions, they often ensue superior properties than salt analogues. A systematic review from perspective design, synthesis, physicochemical evaluation zwitterionic is presented. Depending on parent ring(s) used for synthesis type moieties bearing positive negative charges, different classes materials, such as primary explosives, secondary heat resistant oxidizers, etc., may result. The some also compared with analogous salts. This will encourage readers explore possibility designing new materials.

Язык: Английский

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Polynitro-functionalized 4-phenyl-1H-pyrazoles as heat-resistant explosives

Organic & Biomolecular Chemistry, Год журнала: 2023, Номер 21(32), С. 6604 - 6616

Опубликована: Янв. 1, 2023

This work demonstrates the synthesis, characterization, and energetic properties’ evaluation of polynitro-functionalized 4-phenyl-1 H -pyrazole-based heat-resistant explosives.

Язык: Английский

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Controlling the Energetic Properties of N-Methylene-C-Linked 4-Hydroxy-3,5-dinitropyrazole- and Tetrazole-Based Compounds via a Selective Mono- and Dicationic Salt Formation Strategy

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(21), С. 15085 - 15096

Опубликована: Окт. 17, 2023

In the quest to synthesize high-performing insensitive high-energy density materials (HEDMs), main challenge is establishing an equilibrium between energy and stability. For this purpose, we explored 4-hydroxy-3,5-dinitropyrazole- tetrazole-based energetic scaffolds connected via a N-methylene-C bridge. The hydroxy functionality nitro groups on pyrazole ring promotes physical stability inter- intramolecular hydrogen bonding contributes oxygen balance, supporting better performance. Due two acidic sites (OH NH) with different reactivities, series of monocationic dicationic salts were synthesized, their overall performance was compared. All compounds synthesized in study have high impact sensitivity >40 J friction >360 N. Monocationic generally found thermal respect corresponding salts, which showed salt formation strategy effectively improved 2 (Td = 168 °C), where most decomposition temperatures higher than 220 °C. characterized through IR, multinuclear NMR spectroscopy, high-resolution mass spectrometry (HRMS), elemental analysis. structure-property relationship studied using Hirshfeld surface analysis, noncovalent interaction (NCI) electrostatic potential studies.

Язык: Английский

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Bis(dinitropyrazolyl)methanes spruced up with hydroxyl groups: high performance energetic salts with reduced sensitivity

Chemical Communications, Год журнала: 2023, Номер 59(95), С. 14110 - 14113

Опубликована: Янв. 1, 2023

Superior derivatives of bispyrazolylmethanes, bis(4-hydroxy-3,5-dinitropyrazolyl)methane and its high-performance energetic salts, were synthesized characterized.

Язык: Английский

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N-Acetonitrile functionalized 3-nitrotriazole: Precursor to nitrogen rich stable and insensitive energetic materials

Energetic Materials Frontiers, Год журнала: 2024, Номер 5(1), С. 8 - 16

Опубликована: Фев. 23, 2024

In the field of energetic materials, prime attention has been given to synthesis environmentally compatible materials having an adequate balance between energy and stability. For this purpose, nitrogen-rich heterocyclic rings have contributed as pivotal frameworks. Nitro-functionalized 1,2,4-triazoles profusely used a constituent for synthesizing high-performing (EMs) due their high nitrogen content, good thermal stability, modifiable sites via functionalization. Combination with different scaffold may provide opportunity accessible tailoring. work, in effort investigate potential 3-nitrotriazoles, its N-acetonitrile derivative 2 was synthesized, which further converted various explosophores. N-methylene-C bridged asymmetrically connected tetrazole (3) 1,2,4-oxadiazole (9 10) based EMs synthesized. Further tuning properties salt formation strategy employed compounds 4–7, 11 12. 1,2,4-oxadiazole-based compound 9 also confirmed X-ray diffraction analysis, 10 analyzed 15N NMR spectroscopy. Compounds 3, 4, 5, 7 exhibited stabilities were found be insensitive towards impact friction. 6, detonation performance comparable conventional explosive TATB.

Язык: Английский

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Insights into Structural and Energetic Features of 3,5-Dinitropyrazole-4-carboxylic Acid and Its Energetic Salts

Crystal Growth & Design, Год журнала: 2024, Номер 24(16), С. 6790 - 6799

Опубликована: Июль 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.

Язык: Английский

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Time for mixing: Mixed dicationic energetic salts based on methylene bridged 4-hydroxy-3,5-dinitropyrazole and tetrazole for tunable performance

Energetic Materials Frontiers, Год журнала: 2024, Номер 5(2), С. 105 - 111

Опубликована: Май 14, 2024

Various types of materials have been explored in the pursuit high energy density (HEDMs) that balanced and stability. Among them, energetic salts show numerous advantages, such as lower vapor pressures, physical stabilities, opportunity for favourable tuning by careful selection cations/anions. Nitrogen-rich bases are generally used cations salt formation. While synthesis with larger lowers sensitivity, smaller aid better performance. A combination both same ionic moieties might help formation a superior explosive. In this work, facile route mixed dicationic based on 1-((1H-tetrazol-5-yl)methyl)-3,5-dinitro-1H-pyrazol-4-ol (compound 1) has various combinations bigger (compounds 4-10). All synthesized showed positive heats formation, performance comparable to TATB, excellent stability towards impact friction, acceptable thermal stabilities. This improved technique will provide an additional option fine-tuning properties HEDMs facilitate exploring role overall compounds.

Язык: Английский

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Taming of 4-azido-3,5-dinitropyrazole based energetic materials

Materials Advances, Год журнала: 2023, Номер 5(1), С. 171 - 182

Опубликована: Ноя. 1, 2023

Energetic and physicochemical properties of 4-azido-3,5-dinitropyrazole based energetic compounds were fine-tuned by connecting it to 5-nitramino-1,2,4-oxadiazole moieties via N -methylene- C bridges salt formation strategy.

Язык: Английский

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Combination of N‐amino‐1,2,4‐triazole and 4‐hydroxy‐3,5‐dinitropyrazole for the synthesis of high performing explosives

Journal of Heterocyclic Chemistry, Год журнала: 2024, Номер 61(8), С. 1299 - 1305

Опубликована: Июнь 5, 2024

Abstract In an attempt to cultivate energy‐stability balance, a series of nitrogen and oxygen‐rich high energy density materials were synthesized based on N ‐substituted 4‐hydroxy‐3,5‐dinitropyrazole methylene‐linked ‐amino‐1,2,4‐bridges. The hydroxy substituent contributed oxygen content, hydrogen bonding, tunability via salt formation. On the other hand, triazole bridge delivered content thermal stability. All compounds characterized with multinuclear NMR, FTIR, HRMS, elemental analysis, their physicochemical energetic properties analyzed. Energetic 1 – 5 showed detonation performance adequate overall stabilities. Compound exhibited higher (1.84 g/cm 3 ) ( D v = 8103 m/s, P 26.9 GPa) in comparison its reported amino derivative.

Язык: Английский

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N-Methylene-C-Linked Nitropyrazoles and 1,2,4-Triazolone-3-one: Thermally Stable Energetic Materials with Reduced Sensitivity

Dalton Transactions, Год журнала: 2024, Номер 53(42), С. 17179 - 17189

Опубликована: Янв. 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.

Язык: Английский

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