Embellishing bis-1,2,4-triazole with four nitroamino groups: advanced high-energy-density materials with remarkable performance and good stability

Lang, Qing; Sun, Qi; Wang, Qian; Lin, Qiuhan; Lu, Ming

doi:10.1039/d0ta03008b

Cited by 60 publications

(17 citation statements)

References 40 publications

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“…Crystal structures of HEDMs rich in HBs were shown to have better stability, and expressed enhanced heat resistance and improved insensitivity to impact and shock stimuli , versus compounds with limited HB amount in their crystal structures ( Rupeng et al., 2019 ; Li et al., 2020a , 2020b , 2020c ; Zhang et al., 2019a , 2019b , 2019c , 2019d ). For example, when compared with neutral tetranitroamino HEDMs, corresponding energetic salts showed better thermal and mechanical stabilities, owing to the extensive HB interactions between cations and anions ( Lang et al., 2020 ). However, unfortunately, high content of hydrogen in energetic molecules would in turn lead to decreased ρ and reduced detonation performance of HEDMs.…”

Section: Introductionmentioning

confidence: 99%

Applying machine learning to balance performance and stability of high energy density materials

Huang

Tan

et al. 2021

iScience

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Summary The long-standing performance-stability contradiction issue of high energy density materials (HEDMs) is of extremely complex and multi-parameter nature. Herein, machine learning was employed to handle 28 feature descriptors and 5 properties of detonation and stability of 153 HEDMs, wherein all 21,648 data used were obtained through high-throughput crystal-level quantum mechanics calculations on supercomputers. Among five models, namely, extreme gradient boosting regression tree (XGBoost), adaptive boosting, random forest, multi-layer perceptron, and kernel ridge regression, were respectively trained and evaluated by stratified sampling and 5-fold cross-validation method. Among them, XGBoost model produced the best scoring metrics in predicting the detonation velocity, detonation pressure, heat of explosion, decomposition temperature, and lattice energy of HEDMs, and XGBoost predictions agreed best with the 1,383 experimental data collected from massive literatures. Feature importance analysis was conducted to obtain data-driven insight into the causality of the performance-stability contradiction and delivered the optimal range of key features for more efficient rational design of advanced HEDMs.

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Section: Introductionmentioning

confidence: 99%

Applying machine learning to balance performance and stability of high energy density materials

Huang

Tan

et al. 2021

iScience

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“…Research on energetic salts provides a path to advanced HEDMs because energetic salts usually exhibit a high heat of formation, low vapor pressure, and good stability to thermal and mechanical stimulation. − Dihydroxylammonium 5,5′-bistetrazole-1,1′-diolate (TKX-50) is one representative energetic salt that shows excellent detonation velocity ( D = 9698 m s –1 ) and good molecular stability ( T d = 221 °C, IS = 20 J), which can be rationalized in terms of high lattice energy . It is worth noting that nitrogen-rich cations tend to form a hydrogen bonding network, resulting in insensitivity and a high positive heat of formation. − Therefore, the properties of energetic salts can be modified and enhanced by the rational selection of cations and anions.…”

Section: Introductionmentioning

confidence: 99%

Achieving Good Molecular Stability in Nitrogen-rich Salts Based on Polyamino Substituted Furazan-triazole

Liu

Feng

et al. 2020

Crystal Growth & Design

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Furazan has rarely been used as a building block in the development of energetic cations. In this study, polyamino-substituted furazan-triazole was explored as an energetic cation for the synthesis of energetic salts 3−6. All new compounds were characterized by infrared and NMR spectroscopy, elemental analysis, and single crystal X-ray diffraction. The experimental results revealed that these salts have good thermal stabilities; the decomposition temperatures of these salts, except nitroformate 6, were over 200 °C. These salts (IS: 16−40 J; FS: 200−360 N) are more insensitive than RDX. The noncovalent interaction (NCI) and Hirshfeld surface analyses were performanced to comprehensively study their structure−property relationships. The good molecular stabilities of these salts can arise from (a) abundant π−π interactions on account of the planar furazan-triazole backbone and (b) an extensive hydrogen bonding network resulting from large amounts of amino groups. Simultaneously, all the salts exhibit promising detonation performances (D: 8049−8836 m s −1 ; P: 26.9−34.8 GPa), which were much higher than both those of TNT, and salt 6 was even comparable to RDX.

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“…From the molecular structures, we can see that all compounds contain no water except for compounds 13•H2O and 15•H2O. Additionally, they belong to different crystalline systems with orthorhombic (11), monoclinic (12, 13, 14, and 15), and triclinic (16), respectively. Obviously, all crystals possessed a plane-layered stacked structure formed by several hydrogen bonds and π-π interactions observed from crystal packing pictures.…”

Section: Synthetic Procedures and Structuresmentioning

confidence: 99%

“…The synthesis route was introduced in Scheme 5. 2-methyl-4,5-dicyano-1,2,3-triazole (11) was successfully formed with iodomethane as a methylation agent in 71% yield. 2-methyl-4,5-dicarboxylic acid-1,2,3-triazole (13) was also synthesized from compound 11 via hydrolysis in 89% yield.…”

Section: Synthetic Procedures and Structuresmentioning

confidence: 99%

“…However, only few studies of 1,2,3-triazoles derivatives are reported in the field of energetic materials. At present, the research of energetic materials are concentrate on nitrogen-rich heterocyclic compounds which are furazan [6][7][8], 1,2,4-triazole [9][10][11], and tetrazole [12][13][14]. However, 1,2,3-triazole is a surprisingly stable structure compared to other organic compounds with three contiguous nitrogen atoms [15].…”

Section: Introductionmentioning

confidence: 99%

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4,5-Dicyano-1,2,3-Triazole—A Promising Precursor for a New Family of Energetic Compounds and Its Nitrogen-Rich Derivatives: Synthesis and Crystal Structures

et al. 2021

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The nitrogen-rich compounds and intermediates with structure of monocyclic, bicyclic, and fused rings based on 1,2,3-triazole were synthesized and prepared by using a promising precursor named 4,5-dicyano-1,2,3-triazole, which was obtained by the cyclization reaction of diaminomaleonitrile. Their structure and configurational integrity were assessed by Fourier transform-infrared spectroscopy (FT-IR), mass spectrometry (MS), and elemental analysis (EA). Additionally, fourteen compounds were further confirmed by X-ray single crystal diffraction. Meanwhile, the physical properties of four selected compounds (3·H2O, 6·H2O, 10·H2O, and 16) including thermal stability, detonation parameters, and sensitivity were also estimated. All these compounds could be considered to construct more abundant 1,2,3-triazole-based neutral energetic molecules, salts, and complex compounds, which need to continue study in the future in the field of energetic materials.

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Embellishing bis-1,2,4-triazole with four nitroamino groups: advanced high-energy-density materials with remarkable performance and good stability

Abstract: Tetranitroamino HEDMs based on bis-triazole with comparable performance to CL-20 (D: 9421 and 9609 m s−1) and superior stability.

Cited by 60 publications

References 40 publications

Applying machine learning to balance performance and stability of high energy density materials

Applying machine learning to balance performance and stability of high energy density materials

Achieving Good Molecular Stability in Nitrogen-rich Salts Based on Polyamino Substituted Furazan-triazole

4,5-Dicyano-1,2,3-Triazole—A Promising Precursor for a New Family of Energetic Compounds and Its Nitrogen-Rich Derivatives: Synthesis and Crystal Structures

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