The role of regioisomerism on thermal stability of furoxan based energetic materials

Lv, Meiheng; Zhou, Panwang; Ma, Yinhua; Li, Wenze; Liu, Jianyong

doi:10.1016/j.molstruc.2022.132955

Cited by 7 publications

(5 citation statements)

References 35 publications

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“…Various nitration conditions were evaluated, but ultimately the steric hindrance of the azetidine nitrogen prevented full nitration from occurring (Figure 4C). Regardless, an efficient synthesis of this 2,2,4,4-tetrasubstituted azetidine alcohol (30) demonstrates the power of this synthetic methodology in accessing novel azetidine substitution patterns.…”

Section: ■ Results and Discussionmentioning

confidence: 95%

“…However, studies have shown that stereo- and regiochemistry both influence the physical properties and, consequently, the classification of energetic materials. − It is thus expected that new and superior azetidine-based energetic materials could be developed as functionalized analogues of TNAZ. Despite this potential, the lack of scientific advances in new azetidine-based energetic materials is particularly surprising.…”

Section: Introductionmentioning

confidence: 99%

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Photochemical Strategies Enable the Synthesis of Tunable Azetidine-Based Energetic Materials

et al. 2022

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Despite their favorable properties, azetidines are often overlooked as lead compounds across multiple industries. This is often attributed to the challenging synthesis of densely functionalized azetidines in an efficient manner. In this work, we report the scalable synthesis and characterization of seven azetidines with varying regio- and stereochemistry and their application as novel azetidine-based energetic materials, enabled by the visible-light-mediated aza Paternò–Büchi reaction. The performance and stark differences in the physical properties of these new compounds make them excellent potential candidates as novel solid melt-castable explosive materials, as well as potential liquid propellant plasticizers. This work highlights the scalability and utility of the visible-light aza Paternò–Büchi reaction and demonstrates the impact of stereochemical considerations on the physical properties of azetidine-based energetics. Considering the versatility and efficiency of the presented synthetic strategies, we expect that this work will guide the development of new azetidine-based materials in the energetics space as well as other industries.

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Section: ■ Results and Discussionmentioning

confidence: 95%

Section: Introductionmentioning

confidence: 99%

Photochemical Strategies Enable the Synthesis of Tunable Azetidine-Based Energetic Materials

et al. 2022

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“…Investigating the mechanism of the synthesis path and energy release of EMs assists researchers in the design and synthesis of EMs with superior thermal stabilities. − Compound 2 was simulated and investigated in this study because compounds 5 – 11 were generated from it. The chemical structures of R, Ts1, and Ts2 were optimized (detailed data are provided in the Supporting Information), as shown in Figure ; R represents the reactant, Ts represents the transition state, and P represents the product.…”

Section: Resultsmentioning

confidence: 99%

Construction of High-Performance Energetic MOFs: C₄N₈O₄^2– and C₃N₄O₄^2– with Their Derivatives, Compared with Their Energetic Salts

Zhang

Liu

et al. 2023

Crystal Growth & Design

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A promising strategy for handling the inherent contradiction of energetic materials (EMs, energy vs stability) of energetic metal–organic frameworks and energetic salts is proposed. A series of novel high-performance EMs, energetic metal–organic frameworks of [(C4N8O4 2–)(K+)2(H2O)2], [(C3N4O4 2–)2(Cu2+)2(H2O)4], [(C4HN8O4 –)(K+)(H2O)] and [(C4HN8O4 –) (K+)(H2O)] (2–3 and 5–6) and energetic salts of 7–11, were synthesized, characterized, and fully investigated. The detailed structures and physiochemical properties of 2–3 and 5–8 were obtained by single-crystal X-ray diffraction (XRD). Differential scanning calorimetry, impact sensitivity, and friction sensitivity were measured followed by the simulation and calculation of the ΔH f, noncovalent interaction, detonation velocity and pressure, and Hirshfeld surface to evaluate the comprehensive physiochemical properties of the synthesized substances. The relationships between the thermal stabilities, mechanical sensitivities, and detonation performance with molecular structures of the compounds were fully discussed. Additionally, the reaction transition states and bond dissociation energy of nitro were simulated to investigate the reaction mechanism of the preparation and decomposition of 2 for future studies on EMs.

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“…Isomerization itself can affect the thermal stability of compounds. [80][81][82][83] Rational regional isomerization regulation reduces the repulsive force between nitro groups and is an ideal strategy for developing advanced heatresistant explosives such as 31 and 32 (Fig. 4d).…”

Section: Molecular Functional Group Modificationmentioning

confidence: 99%

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

Li¹,

Pang²,

Miao³

et al. 2023

Phys. Chem. Chem. Phys.

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The role of regioisomerism on thermal stability of furoxan based energetic materials

Cited by 7 publications

References 35 publications

Photochemical Strategies Enable the Synthesis of Tunable Azetidine-Based Energetic Materials

Photochemical Strategies Enable the Synthesis of Tunable Azetidine-Based Energetic Materials

Construction of High-Performance Energetic MOFs: C₄N₈O₄^2– and C₃N₄O₄^2– with Their Derivatives, Compared with Their Energetic Salts

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

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The role of regioisomerism on thermal stability of furoxan based energetic materials

Cited by 7 publications

References 35 publications

Photochemical Strategies Enable the Synthesis of Tunable Azetidine-Based Energetic Materials

Photochemical Strategies Enable the Synthesis of Tunable Azetidine-Based Energetic Materials

Construction of High-Performance Energetic MOFs: C4N8O42– and C3N4O42– with Their Derivatives, Compared with Their Energetic Salts

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

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Construction of High-Performance Energetic MOFs: C₄N₈O₄^2– and C₃N₄O₄^2– with Their Derivatives, Compared with Their Energetic Salts