Azo-linked high-nitrogen energetic materials

Qu, Yanyang; Babailov, Sergey P.

doi:10.1039/c7ta09593g

Cited by 145 publications

(101 citation statements)

References 162 publications

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“…: gas generants, environmentally friendly pyrotechnics) [1][2][3][4][5][6]. A distinctive group is formed by azo-bridged azoles and azines [7]. These compounds have large positive heats of formation and often show remarkable insensitivity toward electrostatic discharge, friction, and impact.…”

Section: Introductionmentioning

confidence: 99%

“…These compounds have large positive heats of formation and often show remarkable insensitivity toward electrostatic discharge, friction, and impact. Moreover, these molecules usually have better performance than parent non-linked heterocycles since they contain the azo explosophore moiety [7]. Amongst the most important energetic azo compounds, there are derivatives of 1,2,3,4-tetrazine ( Figure 1, 1a), tetrazole (1b), 1,2,4-triazole (1c), and pyrazole (1d) [8][9][10][11].…”

Section: Introductionmentioning

confidence: 99%

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Structure and Thermal Properties of 2,2′-Azobis(1H-Imidazole-4,5-Dicarbonitrile)—A Promising Starting Material for a Novel Group of Energetic Compounds

et al. 2020

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A high-nitrogen compound, 2,2′-azobis(1H-imidazole-4,5-dicarbonitrile) (TCAD), was synthesized from commercially available 2-amino-1H-imidazole-4,5-dicarbonitrile. It was characterized with infrared and nuclear magnetic resonance spectroscopy. Its structure was determined by single crystal X-ray diffraction. The crystal of TCAD tetrahydrate is monoclinic, with space group P21/c with crystal parameters of a = 10.2935(2) Å, b = 7.36760(10) Å, c = 20.1447(4) Å, V = 1500.27(5) Å3, Z = 4, and F(000) = 688. Computational methods were used in order to fully optimize the molecular structure, calculate the electrostatic potential of an isolated molecule, and to compute thermodynamic parameters. TCAD has very high thermal stability with temperature of decomposition at 369 °C. Kinetics of thermal decomposition of this compound were studied and apparent energy of activation as well as the maximum safe temperature of technological process were determined.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Structure and Thermal Properties of 2,2′-Azobis(1H-Imidazole-4,5-Dicarbonitrile)—A Promising Starting Material for a Novel Group of Energetic Compounds

et al. 2020

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“…Growing demand for energetic materials in diverse civil, defense, and space applications has increased the need to synthesize them. [19][20][21][22][23][24][25][26][27] In this context, the cost and hazardous nature associated with energetic materials force the use of computational approaches to screen the potential molecules before synthesis. [28][29][30] Given this background, we have inserted [3,4-b]pyrazine (TTFP) backbone (see Figure 2).…”

Section: Introductionmentioning

confidence: 99%

Energetic Triazolo‐Triazolo‐Furazano‐Pyrazines: A Promising Fused Tetracycle Building Block with Diversified Functionalities and Properties

2020

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In this study, high energy materials (HEMs) derived from 1,2,4‐triazolo[3,4‐d]‐1,2,4‐triazolo[3,4‐f]furazano[3,4‐b]pyrazine (TTFP) substituted with −NH2, −NHNO2, −ONO2, −NO2, and −N3 explosophoric groups were designed and computationally characterized. Density functional calculations with B3PW91/6‐31G(d,p) method were used to explore the optimized structures, energetic properties, and sensitivity of TTFP derivatives. It is found that the TTFP is an effective molecular backbone for improving the energy content and energetic performance of the designed compounds. The effect of various explosophoric groups on energy content, density, detonation performance, and sensitivity was investigated. The energetic evaluation indicated that TTFP derivatives having −NHNO2 (F4), −ONO2 (F5), and −NO2 (F6) groups demonstrate good detonation performances and exceed the performance of TNT and close to that of RDX. Compounds F4‐F6 displays the best energetic properties (density > 1.85 g/cm3, detonation velocity >8.30 km/s, detonation pressure > 32.0 GPa). Considering the energetic properties, the TTFP backbone can be regarded as an energy‐rich unit, which can be substituted with suitable explosophoric groups for constructing HEMs.

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“…High energy density compounds (HEDCs, encompassing propellants, explosives and pyrotechnics) as a type of special energy material have attracted significant attention owing to their wide applications in military and civilian. Nowadays, many works have been done in designing and synthesizing novel organic HEDCs with high densities, positive heats of formation, favorable insensitivities, excellent detonation properties, good thermal stabilities, and environmental acceptability . One concept to design new HEDCs is to select proper parent skeletons and extra energetic substituent groups which can increase the heats of formation (Δ H f ) and densities.…”

Section: Introductionmentioning

confidence: 99%

Design of Energetic Materials Based on Asymmetric Oxadiazole

et al. 2019

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A new family of asymmetric oxadiazole based energetic compounds were designed. Their electronic structures, heats of formation, detonation properties and stabilities were investigated by density functional theory. The results show that all the designed compounds have high positive heats of formation ranging from 115.4 to 2122.2 kJ mol−1. −N− bridge/−N3 groups played an important role in improving heats of formation while −O− bridge/−NF2 group made more contributions to the densities of the designed compounds. Detonation properties show that some compounds have equal or higher detonation velocities than RDX, while some other have higher detonation pressures than RDX. All the designed compounds have better impact sensitivities than those of RDX and HMX and meet the criterion of thermal stability. Finally, some of the compounds were screened as the candidates of high energy density compounds with superior detonation properties and stabilities to that of HMX and their electronic properties were investigated.

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Azo-linked high-nitrogen energetic materials

Abstract: In this review, we document the most recent developments in azo-linked heteroaromatic (imidazole, pyrazole, triazole, triazine, tetrazine and oxadiazole) high-nitrogen energetic materials and their salts.

Cited by 145 publications

References 162 publications

Structure and Thermal Properties of 2,2′-Azobis(1H-Imidazole-4,5-Dicarbonitrile)—A Promising Starting Material for a Novel Group of Energetic Compounds

Structure and Thermal Properties of 2,2′-Azobis(1H-Imidazole-4,5-Dicarbonitrile)—A Promising Starting Material for a Novel Group of Energetic Compounds

Energetic Triazolo‐Triazolo‐Furazano‐Pyrazines: A Promising Fused Tetracycle Building Block with Diversified Functionalities and Properties

Design of Energetic Materials Based on Asymmetric Oxadiazole

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