Construction of an Unusual Two-Dimensional Layered Structure for Fused-Ring Energetic Materials with High Energy and Good Stability

Feng, Yongan; Deng, Mucong; Song, Siwei; Chen, Sitong; Zhang, Qinghua; Shreeve, Jean’ne M.

doi:10.1016/j.eng.2020.01.013

Cited by 61 publications

(39 citation statements)

References 45 publications

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“…Two-dimensional (2D) layered structures could transform the mechanical energy acting on a bulk material into relative motion between layers, thus effectively realizing an energy dissipation, which enables many lamellar materials (e.g., graphite, MoS 2 , and h-BN) to be good solid lubricants in critical engineering applications. − Theoretical studies have also confirmed that hydrogen-bond-aided layered structures could convert the external mechanical stimuli acting on HEMs into intermolecular interaction energy via the sliding and compression of the layers, thereby leading to low sensitivity and good safety. − Moreover, representative substances such as 2,4,6-triamino-5-nitropyrimidine 1,3-dioxide (ICM-102), 4-nitro-7-azidopyrazol[3,4- d ]-1,2,3-triazine 2-oxide (NAPTO), 2,4,6-triamino-5-nitropyrimidine-1,3-dioxide hydrogen peroxide (HGI-1), and 4-diaminofurazan 4-amino-3,5-dinitropyrazole (DAF/ADNP) have demonstrated good safety. − However, these examples are usually the result of trial and error or large-scale time-consuming screening. Thus, they are very rare.…”

Section: Introductionsupporting

confidence: 67%

Construction of Layered High-Energy Materials via Directional Hydrogen Bonding

Feng

Wang

2021

Crystal Growth & Design

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Energetic substances with layered crystal packing have been identified as the most promising next-generation high-energy materials (HEMs) due to their excellent insensitivity. The challenge, however, is how to design layered HEMs. In this study, a novel strategy called “acceptor–donor separation” was proposed to control the layer-by-layer stacking of energetic molecules through directional hydrogen boding: that is, a hydrogen bond donor and acceptor are located in different energetic segments and at least one of them has a conjugated planar structure, which will enable the energetic fragments to be infinitely extended in a two-dimensional plane to form a target layered structure. The experimental results showed that three exemplary substances designed by using this strategy possess the expected layered structures, which have been confirmed by single-crystal X-ray diffraction, demonstrating the robustness of this strategy. Moreover, the three as-synthesized HEMs all exhibit excellent insensitivity (impact sensitivity IS > 40 J; friction sensitivity FS > 360 N), affording safety far beyond those of the most powerful HEMs in use today. Especially, the hydroxylammonium energetic salts possess good detonation performance (detonation velocity D = 8924 m s–1; detonation pressure P = 36.9 GPa) comparable to that of 1,3,5-trinitro-1,3,5-triazine (RDX), one of the most powerful high explosives in use today.

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Section: Introductionsupporting

confidence: 67%

Construction of Layered High-Energy Materials via Directional Hydrogen Bonding

Feng

Wang

2021

Crystal Growth & Design

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“…Planar molecular configurations accompanying layer-by-layer compact stacking (planar layered and wavelike layered, Scheme a) are less sensitive than other stacking modes because they can transform the mechanical energy acting on bulk material into relative motion between layers when they are subjected to intense mechanical stimuli. − Additionally, the strong intermolecular hydrogen bonds formed with neighboring molecules and the close π–π packing not only enhance the density of the resulting compound but also cause this kind of compound to be nearly insoluble in water, which decreases acidity and avoids hydrate formation. Examples of these species are TATB, 2,6-diamino-3,5-dinitropyridine-1-oxide (ANPyO), 1,1-diamino-2,2-dinitroethene (FOX-7), and TADNPyO. , Generally speaking, NO 2 , NO, and NHNO 2 are the traditional groups that result in high density in the resulting compounds; − unfortunately, these groups increase the sensitivity of the resulting compounds concomitantly.…”

Section: Introductionmentioning

confidence: 99%

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

Zhang

Feng

et al. 2021

J. Am. Chem. Soc.

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

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“…This stacking mode is one of the key structural characteristics of high-energy insensitive materials, which is helpful in transforming the mechanical energy acting on energetic materials into intermolecular interaction energy through sliding and compression between layers so as to avoid the possible decomposition or explosion of high explosives . This “face-to-face” stacking exists in the classical “wood” explosive, 2,4,6-triamino-1,3,5-trinitrobenzene, and high-energy insensitive explosives, 2,4,6-triamino-5-nitropyrimidine-1,3-dioxide and 4-nitro-7-azido-pyrazol-[3,4- d ]-1,2,3-triazine-2-oxide …”

Section: Results and Discussionmentioning

confidence: 96%

“…30 This "face-to-face" stacking exists in the classical "wood" explosive, 2,4,6-triamino-1,3,5-trinitrobenzene, and high-energy insensitive explosives, 2,4,6-triamino-5nitropyrimidine-1,3-dioxide 31 and 4-nitro-7-azido-pyrazol-[3,4d]-1,2,3-triazine-2-oxide. 32 Compound 2 (CCDC: 2045540) crystallizes in the orthorhombic space group Pbca (no. 61).…”

Section: Resultsmentioning

confidence: 99%

Self-Assembly of Nitrogen-Rich Heterocyclic Compounds with Oxidants for the Development of High-Energy Materials

Zheng

Chen

et al. 2021

ACS Appl. Mater. Interfaces

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The development of energetic materials with high energy and low sensitivity has attracted immense interests due to their widespread applications in aerospace technology and national defense. In this work, a promising self-assembly strategy was developed to prepare three high-energy materials (1–3) through the introduction of oxidant molecules into the crystal voids of the parent materials. The structures of these new materials were comprehensively examined by infrared spectroscopy, nuclear magnetic resonance (NMR) spectroscopy, and single-crystal X-ray diffraction. In these materials, three unique layer structures with hcb, sql, and interrupted sql topologies were observed, which were formed by the fused-ring-based energetic components. Windows with hexagonal, square, and rectangular structures were observed within these layer structures, which were occupied by H2O2, NO3 –, and ClO4 –, respectively. Oxidant molecules interacted with parent molecules via hydrogen bonds to form crystal structures of these materials. Moreover, the energetic property of these materials was estimated by computing methods. The calculation results revealed that these self-assembly materials exhibit excellent energetic properties. The highest energetic performance was observed for compound 3. The detonation velocity, detonation pressure, and specific impulse values were up to 9339 m·s–1, 42.5 GPa, and 308 s, respectively, which were greater than those of HMX. Furthermore, these materials exhibited good sensitivity, which was closely related to their unique crystal structures. The high performance of these materials indicated that the self-assembly strategy should be a promising method for the development of novel energetic materials.

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Construction of an Unusual Two-Dimensional Layered Structure for Fused-Ring Energetic Materials with High Energy and Good Stability

Cited by 61 publications

References 45 publications

Construction of Layered High-Energy Materials via Directional Hydrogen Bonding

Construction of Layered High-Energy Materials via Directional Hydrogen Bonding

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

Self-Assembly of Nitrogen-Rich Heterocyclic Compounds with Oxidants for the Development of High-Energy Materials

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