Pub Date : 2025-09-01DOI: 10.1016/j.enmf.2024.09.001
Jie Li , Yu-bing Liu , Wen-qi Ma , Si-ping Pang , Lu Hu , Chun-lin He
A mild and efficient way to form fused N→O moiety by in situ ring closure reaction was proposed and studied. Compared with other methods to synthesize fused N-oxides, the new strategy is much safer and easier. The obtained compound, 4-amino-7-nitro-[1,2,4]triazolo[5,1-d][1,2,3,5]tetrazine-2-N-oxide (NTTO), was isolated with good purity and fully characterized. NTTO has a high density of 1.841 g⋅cm−3 and a high decomposition temperature of 262 °C. Compared with the traditional high energy insensitive energetic compound FOX-7, NTTO shows a higher detonation velocity of 8907 m⋅s−1 and lower sensitivity (IS = 40 J, FS = 252 N), demonstrating a promising candidate as a high energy insensitive energetic material. Compared with the traditional ortho-C-amino/C-nitro structure, the formed 4-amino-1,2,3,5-tetrazine-2-oxide ring shows greater promise in designing energetic materials with high energy and low sensitivity.
提出并研究了一种温和高效的原位闭合反应生成N→O熔合基团的方法。与其他合成熔融n氧化物的方法相比，该方法更安全、更容易。分离得到的化合物4-氨基-7-硝基-[1,2,4]三唑[5,1-d][1,2,3,5]四氮-2- n -氧化物（NTTO）纯度高，并进行了完整的表征。NTTO的密度为1.841 g⋅cm−3，分解温度为262℃。与传统的高能不敏感能化合物FOX-7相比，NTTO的爆速高达8907 m·s−1，灵敏度较低（IS = 40 J, FS = 252 N），是一种很有前景的高能不敏感能材料。与传统的邻c -氨基/ c -硝基结构相比，形成的4-氨基-1,2,3,5-四氮-2-氧化物环在设计高能量低灵敏度的含能材料方面具有更大的前景。
{"title":"Construction of fused N-oxide via in situ ring closure strategy: New pathway to high energy low sensitivity energetic compounds","authors":"Jie Li , Yu-bing Liu , Wen-qi Ma , Si-ping Pang , Lu Hu , Chun-lin He","doi":"10.1016/j.enmf.2024.09.001","DOIUrl":"10.1016/j.enmf.2024.09.001","url":null,"abstract":"<div><div>A mild and efficient way to form fused N→O moiety by in situ ring closure reaction was proposed and studied. Compared with other methods to synthesize fused N-oxides, the new strategy is much safer and easier. The obtained compound, 4-amino-7-nitro-[1,2,4]triazolo[5,1-<em>d</em>][1,2,3,5]tetrazine-2-<em>N</em>-oxide (NTTO), was isolated with good purity and fully characterized. NTTO has a high density of 1.841 g⋅cm<sup>−3</sup> and a high decomposition temperature of 262 °C. Compared with the traditional high energy insensitive energetic compound FOX-7, NTTO shows a higher detonation velocity of 8907 m⋅s<sup>−1</sup> and lower sensitivity (<em>IS</em> = 40 J, <em>FS</em> = 252 N), demonstrating a promising candidate as a high energy insensitive energetic material. Compared with the traditional ortho-C-amino/C-nitro structure, the formed 4-amino-1,2,3,5-tetrazine-2-oxide ring shows greater promise in designing energetic materials with high energy and low sensitivity.</div></div>","PeriodicalId":34595,"journal":{"name":"Energetic Materials Frontiers","volume":"6 3","pages":"Pages 284-290"},"PeriodicalIF":3.9,"publicationDate":"2025-09-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145365854","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Energetic materials are capable of storing vast amounts of chemical energy and releasing it over a very short period of time, leading to an irreplaceable usage in both military and civilian applications. From traditional nitro compounds to nitrogen-rich heterocyclic energetic compounds, a large number of high-performance energetic molecules have been synthesized. Recently, several promising strategies have been developed for the efficient synthesis, performances tuning, and properties prediction of energetic compounds, which are expected to reshape the field of energetic materials. Here we highlight and discuss several representative examples to show the latest advances and promote the development of this field.
{"title":"Synthetic chemistry of energetic materials: Evolution, current trends, and AI-driven future","authors":"Zhi-wei Zeng, Yong-xing Tang, Hong-wei Yang, Guang-bin Cheng","doi":"10.1016/j.enmf.2025.09.001","DOIUrl":"10.1016/j.enmf.2025.09.001","url":null,"abstract":"<div><div>Energetic materials are capable of storing vast amounts of chemical energy and releasing it over a very short period of time, leading to an irreplaceable usage in both military and civilian applications. From traditional nitro compounds to nitrogen-rich heterocyclic energetic compounds, a large number of high-performance energetic molecules have been synthesized. Recently, several promising strategies have been developed for the efficient synthesis, performances tuning, and properties prediction of energetic compounds, which are expected to reshape the field of energetic materials. Here we highlight and discuss several representative examples to show the latest advances and promote the development of this field.</div></div>","PeriodicalId":34595,"journal":{"name":"Energetic Materials Frontiers","volume":"6 3","pages":"Pages 267-276"},"PeriodicalIF":3.9,"publicationDate":"2025-09-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145365856","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-09-01DOI: 10.1016/j.enmf.2025.02.005
Dmitry V. Khakimov, Leonid L. Fershtat, Tatyana S. Pivina
Using the methods of quantum chemistry and atom-atom potentials, the molecular and crystal structure of a number of nitromethanes and their salts was modeled. Their thermochemical characteristics were assessed. A comparison of the calculated values of the enthalpies of salt formation with experimental data known for some of the presented compounds indicates that the author's method (MICCM), based on modeling the structure of compounds of ionic form and their cocrystals, gives the most accurate values of the enthalpy of salt formation compared to other known calculation methods. As a result of the simulation, the structure was predicted and the enthalpies of previously unstudied salts were determined, as well as new, unknown polymorphic structures of neutral nitromethanes and their salts.
{"title":"Theoretical study of the structure and energy performance of nitroformates and mono-, di-, tri- and tetranitromethanes","authors":"Dmitry V. Khakimov, Leonid L. Fershtat, Tatyana S. Pivina","doi":"10.1016/j.enmf.2025.02.005","DOIUrl":"10.1016/j.enmf.2025.02.005","url":null,"abstract":"<div><div>Using the methods of quantum chemistry and atom-atom potentials, the molecular and crystal structure of a number of nitromethanes and their salts was modeled. Their thermochemical characteristics were assessed. A comparison of the calculated values of the enthalpies of salt formation with experimental data known for some of the presented compounds indicates that the author's method (MICCM), based on modeling the structure of compounds of ionic form and their cocrystals, gives the most accurate values of the enthalpy of salt formation compared to other known calculation methods. As a result of the simulation, the structure was predicted and the enthalpies of previously unstudied salts were determined, as well as new, unknown polymorphic structures of neutral nitromethanes and their salts.</div></div>","PeriodicalId":34595,"journal":{"name":"Energetic Materials Frontiers","volume":"6 3","pages":"Pages 362-369"},"PeriodicalIF":3.9,"publicationDate":"2025-09-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145365965","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-09-01DOI: 10.1016/j.enmf.2025.03.001
Zi-wu Cai, Tian-yu Jiang, Wen-quan Zhang
For energetic compounds with a specific composition, isomerism represents the significant factor influencing their physicochemical properties. It is therefore becoming increasingly important to gain an understanding of the influence of isomerism on property differences on energetic materials. Despite significant advancements in the field of energetic molecular isomerization, research has predominantly concentrated on positional isomerization of functional groups, with comparatively less emphasis placed on molecular skeleton isomerization. In this study, we examine two isomeric fused-ring energetic molecules, ICM-103 and NAPTO, which display markedly disparate properties, including thermal decomposition temperature and mechanical sensitivity, despite sharing identical functional groups and fundamental structural units. We employed static calculations to examine and elucidate how molecular skeleton isomerism causes the performance differences between ICM-103 and NAPTO from the perspectives of single molecular parameters, intermolecular interactions, and crystal packing. This work offers a valuable reference point for the design of energetic molecular structures and the analysis of the relationships between structure and activity.
{"title":"Understanding how molecular skeletal isomerism affects the stability of energetic fused-ring molecules: A comparative study of ICM-103 and NAPTO","authors":"Zi-wu Cai, Tian-yu Jiang, Wen-quan Zhang","doi":"10.1016/j.enmf.2025.03.001","DOIUrl":"10.1016/j.enmf.2025.03.001","url":null,"abstract":"<div><div>For energetic compounds with a specific composition, isomerism represents the significant factor influencing their physicochemical properties. It is therefore becoming increasingly important to gain an understanding of the influence of isomerism on property differences on energetic materials. Despite significant advancements in the field of energetic molecular isomerization, research has predominantly concentrated on positional isomerization of functional groups, with comparatively less emphasis placed on molecular skeleton isomerization. In this study, we examine two isomeric fused-ring energetic molecules, ICM-103 and NAPTO, which display markedly disparate properties, including thermal decomposition temperature and mechanical sensitivity, despite sharing identical functional groups and fundamental structural units. We employed static calculations to examine and elucidate how molecular skeleton isomerism causes the performance differences between ICM-103 and NAPTO from the perspectives of single molecular parameters, intermolecular interactions, and crystal packing. This work offers a valuable reference point for the design of energetic molecular structures and the analysis of the relationships between structure and activity.</div></div>","PeriodicalId":34595,"journal":{"name":"Energetic Materials Frontiers","volume":"6 3","pages":"Pages 332-339"},"PeriodicalIF":3.9,"publicationDate":"2025-09-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145365962","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-09-01DOI: 10.1016/j.enmf.2024.07.002
Tian Lei , Yan-da Jiang , Bao-jing Tian , Ning Ding , Qi Sun , Sheng-hua Li , Si-ping Pang
Most energetic molecules can only form cations or anions, limiting the structural diversity and performance regulation. In this study, we have presented the interesting amphoteric feature of 3,5-diamino-6-hydroxy-2-oxide-4-nitropyrimidone (DHON), which can be transformed into both DHON− anion and DHON+ cation. The structures of the amphoteric salts were characterized by using single-crystal x-ray diffraction, and their energy (density, heat of formation, detonation velocity, and detonation pressure) and stability (thermal decomposition temperature, impact sensitivity, and friction sensitivity) were also carefully studied. Results indicate DHON− anionic salts exhibit very promising stabilities, much superior to DHON+ cationic salts. Especially, the hydroxylaminium salt exhibits an extremely high thermal decomposition temperature of 309 °C. The x-ray data and quantum calculations show that the DHON− anion has stronger conjugation and H-bonds than the DHON+ cation, thus leading to the higher stability.
大多数高能分子只能形成阳离子或阴离子，从而限制了结构的多样性和性能的调节。在这项研究中，我们提出了 3,5-二氨基-6-羟基-2-氧化物-4-硝基嘧啶酮（DHON）有趣的两性特征，它既可以转化为 DHON 阴离子，也可以转化为 DHON 阳离子。利用单晶 X 射线衍射表征了两性盐的结构，并仔细研究了它们的能量（密度、形成热、爆速和爆压）和稳定性（热分解温度、冲击敏感性和摩擦敏感性）。结果表明，DHON 阴离子盐的稳定性非常好，远远优于 DHON 阳离子盐。X 射线数据和量子计算表明，DHON 阴离子比 DHON 阳离子具有更强的共轭和 H 键，因此具有更高的稳定性。
{"title":"Amphoteric feature of 3,5-diamino-6-hydroxy-2-oxide-4-nitropyrimidone and its highly-stable energetic anionic salts","authors":"Tian Lei , Yan-da Jiang , Bao-jing Tian , Ning Ding , Qi Sun , Sheng-hua Li , Si-ping Pang","doi":"10.1016/j.enmf.2024.07.002","DOIUrl":"10.1016/j.enmf.2024.07.002","url":null,"abstract":"<div><div>Most energetic molecules can only form cations or anions, limiting the structural diversity and performance regulation. In this study, we have presented the interesting amphoteric feature of 3,5-diamino-6-hydroxy-2-oxide-4-nitropyrimidone (DHON), which can be transformed into both DHON<sup>−</sup> anion and DHON<sup>+</sup> cation. The structures of the amphoteric salts were characterized by using single-crystal x-ray diffraction, and their energy (density, heat of formation, detonation velocity, and detonation pressure) and stability (thermal decomposition temperature, impact sensitivity, and friction sensitivity) were also carefully studied. Results indicate DHON<sup>−</sup> anionic salts exhibit very promising stabilities, much superior to DHON<sup>+</sup> cationic salts. Especially, the hydroxylaminium salt exhibits an extremely high thermal decomposition temperature of 309 °C. The x-ray data and quantum calculations show that the DHON<sup>−</sup> anion has stronger conjugation and H-bonds than the DHON<sup>+</sup> cation, thus leading to the higher stability.</div></div>","PeriodicalId":34595,"journal":{"name":"Energetic Materials Frontiers","volume":"6 3","pages":"Pages 340-346"},"PeriodicalIF":3.9,"publicationDate":"2025-09-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141770484","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-09-01DOI: 10.1016/j.enmf.2024.06.005
Long Zhu , Qi Zhou , Wei Wang , Huan Li , Bing Li , Yu Zhang , Jun Luo
Organic cage-like frameworks are important and versatile skeletons for developing prospective energetic compounds because of their high intrinsic density, symmetry, stability, and derivability. In this paper, a noradamantane-based energetic compound 3,7-dinitrato-9-nitro-9-azanoradamantane was synthesized from easily accessible compound 1,6-heptadien-4-ol via eight steps. Based on the X-ray diffraction analysis, it exhibits a good density of 1.678 g⋅cm−3. Thermogravimetry (TG) and differential scanning calorimetry (DSC) tests indicate that it has positive thermal stability since its decomposition temperature was found to be 134 °C, and the theoretical detonation velocity is calculated to be 7363 m⋅s−1. These results imply that noradamantane has the potential to be a prospective framework for developing high energy-density energetic compounds.
{"title":"Synthesis and characterization of a new cage-like energetic compound 3,7-dinitrato-9-nitro-9-azanoradamantane","authors":"Long Zhu , Qi Zhou , Wei Wang , Huan Li , Bing Li , Yu Zhang , Jun Luo","doi":"10.1016/j.enmf.2024.06.005","DOIUrl":"10.1016/j.enmf.2024.06.005","url":null,"abstract":"<div><div>Organic cage-like frameworks are important and versatile skeletons for developing prospective energetic compounds because of their high intrinsic density, symmetry, stability, and derivability. In this paper, a noradamantane-based energetic compound 3,7-dinitrato-9-nitro-9-azanoradamantane was synthesized from easily accessible compound 1,6-heptadien-4-ol via eight steps. Based on the X-ray diffraction analysis, it exhibits a good density of 1.678 g⋅cm<sup>−3</sup>. Thermogravimetry (TG) and differential scanning calorimetry (DSC) tests indicate that it has positive thermal stability since its decomposition temperature was found to be 134 °C, and the theoretical detonation velocity is calculated to be 7363 m⋅s<sup>−1</sup>. These results imply that noradamantane has the potential to be a prospective framework for developing high energy-density energetic compounds.</div></div>","PeriodicalId":34595,"journal":{"name":"Energetic Materials Frontiers","volume":"6 3","pages":"Pages 277-283"},"PeriodicalIF":3.9,"publicationDate":"2025-09-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141509273","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-09-01DOI: 10.1016/j.enmf.2025.03.003
Pin-xu Zhao , Xun Huang , Hai-feng Huang , Jun Yang
The safety of polynitro 1,2,3-triazole energetic materials is improved by introducing hydrogen-rich cation and N-amino group to strengthen the intermolecular hydrogen bond network. 2-Amino-4-nitro-5-dinitromethyl-1H-1,2,3-triazole and its corresponding energetic salts were successfully prepared, and they exhibit excellent properties compared to 4-nitro-5-dinitromethyl-1H-1,2,3-triazole compounds. Among them, Hydroxylaminium 2-amino-4-nitro-5-dinitromethyl-1H-1,2,3-triazole (7) showed the best detonation performances (Dv = 9389 m·s−1, p = 39.6 GPa), which are compatible with that of HMX (Dv = 9320 m·s−1, p = 39.5 GPa) and it also show acceptable sensitivities (IS = 7 J, FS = 80 N).
{"title":"Polynitro 1,2,3-triazole energetic materials with excellent properties through the combination of hydrogen-rich cation and N-amino group","authors":"Pin-xu Zhao , Xun Huang , Hai-feng Huang , Jun Yang","doi":"10.1016/j.enmf.2025.03.003","DOIUrl":"10.1016/j.enmf.2025.03.003","url":null,"abstract":"<div><div>The safety of polynitro 1,2,3-triazole energetic materials is improved by introducing hydrogen-rich cation and <em>N</em>-amino group to strengthen the intermolecular hydrogen bond network. 2-Amino-4-nitro-5-dinitromethyl-1<em>H</em>-1,2,3-triazole and its corresponding energetic salts were successfully prepared, and they exhibit excellent properties compared to 4-nitro-5-dinitromethyl-<em>1H</em>-1,2,3-triazole compounds. Among them, Hydroxylaminium 2-amino-4-nitro-5-dinitromethyl-<em>1H</em>-1,2,3-triazole (<strong>7</strong>) showed the best detonation performances (<em>D</em><sub><em>v</em></sub> = 9389 m·s<sup>−1</sup>, <em>p</em> = 39.6 GPa), which are compatible with that of HMX (<em>D</em><sub><em>v</em></sub> = 9320 m·s<sup>−1</sup>, <em>p</em> = 39.5 GPa) and it also show acceptable sensitivities (IS = 7 J, FS = 80 N).</div></div>","PeriodicalId":34595,"journal":{"name":"Energetic Materials Frontiers","volume":"6 3","pages":"Pages 305-311"},"PeriodicalIF":3.9,"publicationDate":"2025-09-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145365804","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-09-01DOI: 10.1016/j.enmf.2025.06.002
Xin-yu Du , Qi Lai , Yun-bin Liu , Gang Zhao , Ping Yin , Si-ping Pang
Green high-energy oxidizers are significant for solid propellants due to the reported health and environmental issues of current halogen-containing benchmark material, ammonium perchlorate. Traditional approaches to azole-based oxidizers are often hindered by multi-step reactions, prolonged reaction times, or compatibility issues in formulation studies. In this contribution, we report a two-step concise synthetic route to access pentanitropyrazole that simultaneously introduces versatile energetic functionalities, i.e., C-nitro, N-nitro, and C-trinitromethyl groups, using commercially available starting materials. Full characterization is carried out to evaluate the overall performance using experimental analysis and theoretical calculations. The newly synthesized compound achieves a high crystal density of 1.935 g·cm−3 (170 K), a positive oxygen balance of 28.7 %, and excellent detonation performance, outperforming the literature-reported pentanitro-functionalized analogues. Furthermore, its simplified synthesis and positive oxygen balance highlight its great potential as a green replacement for AP.
{"title":"Two-step facile access to a novel pyrazole-based high energy density oxidizer via pentanitro-functionalization","authors":"Xin-yu Du , Qi Lai , Yun-bin Liu , Gang Zhao , Ping Yin , Si-ping Pang","doi":"10.1016/j.enmf.2025.06.002","DOIUrl":"10.1016/j.enmf.2025.06.002","url":null,"abstract":"<div><div>Green high-energy oxidizers are significant for solid propellants due to the reported health and environmental issues of current halogen-containing benchmark material, ammonium perchlorate. Traditional approaches to azole-based oxidizers are often hindered by multi-step reactions, prolonged reaction times, or compatibility issues in formulation studies. In this contribution, we report a two-step concise synthetic route to access pentanitropyrazole that simultaneously introduces versatile energetic functionalities, i.e., C-nitro, N-nitro, and C-trinitromethyl groups, using commercially available starting materials. Full characterization is carried out to evaluate the overall performance using experimental analysis and theoretical calculations. The newly synthesized compound achieves a high crystal density of 1.935 g·cm<sup>−3</sup> (170 K), a positive oxygen balance of 28.7 %, and excellent detonation performance, outperforming the literature-reported pentanitro-functionalized analogues. Furthermore, its simplified synthesis and positive oxygen balance highlight its great potential as a green replacement for AP.</div></div>","PeriodicalId":34595,"journal":{"name":"Energetic Materials Frontiers","volume":"6 3","pages":"Pages 312-317"},"PeriodicalIF":3.9,"publicationDate":"2025-09-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145365805","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
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