Fused heterocycle-based energetic materials (2012–2019)

Journal of Materials Chemistry A, Journal Year: 2020, Volume and Issue: 8(8), P. 4193 - 4216

Published: Jan. 1, 2020

Fused heterocycles are unique building blocks for the synthesis of a wide range high-performance energetic materials.

Language: Английский

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Accelerating the discovery of insensitive high-energy-density materials by a materials genome approach

Nature Communications, Journal Year: 2018, Volume and Issue: 9(1)

Published: June 18, 2018

Finding new high-energy-density materials with desired properties has been intensely-pursued in recent decades. However, the contradictory relationship between high energy and low mechanical sensitivity makes innovation of insensitive an enormous challenge. Here, we show how a genome approach can be used to accelerate discovery high-energy explosives by identification "genetic" features, rapid molecular design, screening, as well experimental synthesis target molecule, 2,4,6-triamino-5-nitropyrimidine-1,3-dioxide. This as-synthesized energetic compound exhibits graphite-like layered crystal structure measured density 1.95 g cm-3, thermal decomposition temperature 284 °C, detonation velocity 9169 m s-1, extremely sensitivities (impact sensitivity, >60 J friction >360 N). Besides considered system six-member aromatic hetero-aromatic rings, this also applicable development high-performing materials.

Language: Английский

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

Chemical Reviews, Journal Year: 2020, Volume and Issue: 120(12), P. 5682 - 5744

Published: June 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.

Language: Английский

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Balancing Excellent Performance and High Thermal Stability in a Dinitropyrazole Fused 1,2,3,4-Tetrazine

Journal of the American Chemical Society, Journal Year: 2017, Volume and Issue: 139(39), P. 13684 - 13687

Published: Sept. 14, 2017

The key to successfully designing high-performance and insensitive energetic compounds for practical applications is through adjusting the molecular organization including both fuel oxidizer. Now a superior hydrogen-free 5/6/5 fused ring material, 1,2,9,10-tetranitrodipyrazolo[1,5-d:5',1'-f][1,2,3,4]tetrazine (6) obtained from 4,4',5,5'-tetranitro-2H,2'H-3,3'-bipyrazole (4) by N-amination N-azo coupling reactions described. structures of 5 6 were confirmed single crystal X-ray diffraction measurements. Compound has remarkable room temperature experimental density 1.955 g cm-3 shows excellent detonation performance. In addition, it high decomposition 233 °C. These fascinating properties, which are comparable those CL-20, make very attractive in performance applications.

Language: Английский

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Recent synthetic efforts towards high energy density materials: How to design high-performance energetic structures?

FirePhysChem, Journal Year: 2021, Volume and Issue: 2(2), P. 83 - 139

Published: Oct. 1, 2021

Energetic material is a very essential company of compounds, widely used in various fields, primarily the military industry and space technologies. These compounds are unique that they capable instantly decomposing to release enormous energy. The chemical diversity energetic organic constantly increasing through combination high-nitrogen frameworks explosophoric groups, which follows overall trend interest their chemistry applications. scientific community looking for more powerful less sensitive external impulses both civilian use. Herein, detailed overview regarding classic novel groups frameworks, as well description selected synthesis target has been given time period since 2010. physical properties performances benchmark prospective also collected.

Language: Английский

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

Journal of the American Chemical Society, Journal Year: 2018, Volume and Issue: 140(44), P. 15001 - 15007

Published: Oct. 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

Language: Английский

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Aminonitro Groups Surrounding a Fused Pyrazolotriazine Ring: A Superior Thermally Stable and Insensitive Energetic Material

ACS Applied Energy Materials, Journal Year: 2019, Volume and Issue: 2(3), P. 2263 - 2267

Published: Feb. 12, 2019

Nitrogen-rich heterocyclic compounds offer promising potential backbones for constructing various high energy density compounds. Selective diazotization of 3,5-diamino-4-nitropyrazole (1) with tert-butyl nitrite followed by treatment the sodium salt nitroacetonitrile gives rise to a fused pyrazolotriazine ring (5) surrounded amino and nitro groups. Compound 5, confirmed single-crystal X-ray diffraction, has remarkable thermal decomposition temperature 355 °C, 1.90 g cm–3, low impact friction sensitivities. The detonation performance is also superior TATB. These advantages make 5 candidate as heat-resistant explosive.

Language: Английский

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Polynitro‐Functionalized Dipyrazolo‐1,3,5‐triazinanes: Energetic Polycyclization toward High Density and Excellent Molecular Stability

Angewandte Chemie International Edition, Journal Year: 2017, Volume and Issue: 56(30), P. 8834 - 8838

Published: May 30, 2017

A new fused N-heterocyclic framework, dipyrazolo-1,3,5-triazinane, was synthesized and the physiochemical properties of its derivatives were investigated to evaluate integrated energetic performance. In contrast 1,3,5-trinitro-1,3,5-triazinane (RDX) featuring a distorted chair confirmation, polynitro-functionalized dipyrazolo-1,3,5-triazinanes have nearly planar backbones, thereby enhancing density thermal stability. Among these tricyclic compounds, 5 12 show favorable crystal densities 1.937 g cm-3 1.990 at 150 K, respectively, which rank highest in triazinane-based compounds. Additionally, this synthetic approach carried out form seven-membered eight-membered rings, giving rise tetranitro dipyrazolo-1,3,5-triazepane (5 b) dipyrazolo-1,3,5-triazocane c), respectively.

Language: 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, Journal Year: 2019, Volume and Issue: 7(13), P. 7875 - 7884

Published: Jan. 1, 2019

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

Language: Английский

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Amino-tetrazole functionalized fused triazolo-triazine and tetrazolo-triazine energetic materials

Chemical Communications, Journal Year: 2019, Volume and Issue: 55(43), P. 6062 - 6065

Published: Jan. 1, 2019

In this study, two insensitive energetic compounds using fused triazolo-triazine and tetrazolo-triazine as the framework, one amino tetrazole functional groups, were prepared through a two-step reaction.

Language: Английский

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