Properties and Promise of Catenated Nitrogen Systems As High-Energy-Density Materials

Chemical Reviews, Год журнала: 2020, Номер 120(12), С. 5682 - 5744

Опубликована: Июнь 16, 2020

The properties of catenated nitrogen molecules, molecules containing internal chains bonded atoms, is fundamental scientific interest in chemical structure and bonding, as uniquely situated the periodic table to form kinetically stable compounds often with chemically N–N bonds but which are thermodynamically unstable that formation multiply N2 usually preferable. This unique placement makes for development high-energy-density materials, including explosives defense construction purposes, well propellants missile propulsion space exploration. review, designed a audience, describes foundational subjects, methods, metrics relevant energetic materials community provides an overview important classes ranging from theoretical investigation hypothetical practical application real-world materials. review intended provide detailed insight into synthesis decomposition such knowledge science new most chemists.

Язык: Английский

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A green metal-free fused-ring initiating substance

Nature Communications, Год журнала: 2019, Номер 10(1)

Опубликована: Март 22, 2019

Abstract Over the past century, search for lead-free, environmentally friendly initiating substances has been a highly challenging task in field of energetic materials. Here, an organic primary explosive featuring fused-ring structure, 6-nitro-7-azido-pyrazol[3,4-d][1,2,3]triazine-2-oxide, was designed and synthesized through facile two-step reaction from commercially available reagents. This substance meets nearly all stringent criteria explosives commercial applications: it is free toxic metals perchlorate, high density, priming ability, unusual sensitivities towards non-explosive stimuli, excellent environmental resistance, decent thermal stability, detonation performance, satisfactory flowability pressure durability, low-cost easy to scale-up. These combined properties performance measures surpass current widely used explosive, DDNP. The reported herein may find real-world application as device near future.

Язык: Английский

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Zwitterionic fused pyrazolo-triazole based high performing energetic materials

Chemical Communications, Год журнала: 2024, Номер 60(12), С. 1646 - 1649

Опубликована: Янв. 1, 2024

A series of nitrogen-rich fused energetic materials were synthesized from commercially available inexpensive starting and fully characterized using 1 H 13 C NMR, IR spectroscopy, elemental analysis, DSC.

Язык: Английский

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Conjugated Energetic Salts Based on Fused Rings: Insensitive and Highly Dense Materials

Journal of the American Chemical Society, Год журнала: 2018, Номер 140(44), С. 15001 - 15007

Опубликована: Окт. 17, 2018

Nitroamino-functionalized 1,2,4-triazolo[4,3- b][1,2,4,5]tetrazine (1), when combined with intermolecular hydrogen bonds (HBs) and strong noncovalent interactions between layers, results, for example, in an interlayer distance of 2.9 Å dihydroxylammonium 3,6-dinitramino-1,2,4-triazolo[4,3- (2c) a packing coefficient 0.805. For 6,6'-dinitramino-3,3'-azo-1,2,4-triazolo[4,3- (3b), two fused rings are linked by azo group, which expands the conjugated system resulting even shorter 2.7 higher 0.807. These values appear to be shortest distances highest coefficients reported tetrazine energetic materials. With high coefficients, both possess densities 1.92 g cm-3 1.99 at 293 K, respectively. Compared its precursor, hydroxylammonium moiety serves as buffer chain (H-N-O-H), connecting anion cation through bonds, giving rise more favorable stacking, density lower sensitivity. The sensitivities all salts than that their neutral precursors, such compound 2 (3 J, >5 N) 2c (25 360 N). detonation properties (detonation velocity vD = 9712 m s-1 pressure P 43 GPa) 3b (vD 10233 s-1; 49 exceed those present explosive benchmarks, octahydro-1,3,5,7-tetranitro-1,3,5,7-tetrazocine (HMX) hexanitrohexaazaisowurzitane (CL-20). molecular structures several these new materials confirmed single-crystal X-ray diffraction measurements. Using calculated experimental ring planar large π-conjugated results compromise desirable stabilities properties, thus enhancing future utilization design

Язык: Английский

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Multipurpose [1,2,4]triazolo[4,3-b][1,2,4,5] tetrazine-based energetic materials

Journal of Materials Chemistry A, Год журнала: 2019, Номер 7(13), С. 7875 - 7884

Опубликована: Янв. 1, 2019

Next-generation fused ring energetic materials for different applications were designed by regulating mechanical sensitivity.

Язык: Английский

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5,6-Fused bicyclic tetrazolo-pyridazine energetic materials

Chemical Communications, Год журнала: 2020, Номер 56(10), С. 1493 - 1496

Опубликована: Янв. 1, 2020

Two 5,6-fused tetrazolo-pyridazine compounds were synthesized and characterized, which exhibited high thermal stability, excellent energetic properties low mechanical sensitivity.

Язык: Английский

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One Step Closer to an Ideal Insensitive Energetic Molecule: 3,5-Diamino-6-hydroxy-2-oxide-4-nitropyrimidone and its Derivatives

Journal of the American Chemical Society, Год журнала: 2021, Номер 143(32), С. 12665 - 12674

Опубликована: Авг. 5, 2021

Reaching the goal of developing an insensitive high-energy molecule (IHEM) is a major challenge. In this study, 3,5-diamino-6-hydroxy-2-oxide-4-nitropyrimidone (IHEM-1) was synthesized in one step from 2,4,6-triamino-5-nitropyrimidine-1,3-dioxide hydrate (ICM-102 hydrate). The density compound IHEM-1 1.95 g cm–3 with decomposition temperature 271 °C. Its detonation velocity and pressure are 8660 m s–1 33.64 GPa, respectively, which far superior to performance 1,3,5-triamino-2,4,6-trinitrobenzene (TATB), while its sensitivity identical that TATB. addition, four derivatives (1a, chloride; 1b, nitrate; 1c, perchlorate; 1d, dinitramide) were prepared on basis weak base site (N–O group) show excellent energetic properties. By combining series advantages, including simple preparation, high yield, density, very low solubility aqueous solution, thermostability, insensitivity, performance, approaches ideal molecule. Compounds 1b–1d also competitive as new high-energy-density materials.

Язык: Английский

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Desensitization of the dinitromethyl group: molecular/crystalline factors that affect the sensitivities of energetic materials

Journal of Materials Chemistry A, Год журнала: 2018, Номер 6(45), С. 22705 - 22712

Опубликована: Янв. 1, 2018

The dinitromethyl group has attracted considerable attention because of its high nitrogen and oxygen content, positive balance energy.

Язык: Английский

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Thermal stability of azole-rich energetic compounds: their structure, density, enthalpy of formation and energetic properties

Physical Chemistry Chemical Physics, Год журнала: 2023, Номер 25(28), С. 18523 - 18544

Опубликована: Янв. 1, 2023

Increasing the strength and number of hydrogen bonds azoles expanding π–π stacking area are key factors to improve thermal stability, which provides a valuable way for developing energetic materials with higher energy stability.

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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