CHINESE JOURNAL OF ENERGETIC MATERIALS
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1,2,5-噁二唑桥联双1,2,4-噁二唑化合物的合成及性能
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南京理工大学化学与化工学院

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国家自然科学基金(22538009,22505109,22505110),江苏省自然科学基金(BK20220958),中国博士后科学基金(2024M764227,2023M741696),航天化学动力国家重点实验室开放研究基金项目


Synthesis and Properties of Energetic Compounds Based on 1,2,5-Oxadiazole-bridged Bis(1,2,4-oxadiazole)
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School of Chemistry and Chemical Engineering, Nanjing University of Science and Technology

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Grant support: National Natural Science Foundation of China (Nos. 22538009, 22505109, 22505110), Natural Science Foundation of Jiangsu Province (BK20220958) , China Postdoctoral Science Foundation (2024M764227, 2023M741696), and Open Research Fund Program of National Key Laboratory of Aerospace Chemical Power

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    摘要:

    氧化呋咱由于具有“潜硝基”结构而拥有高能量被广泛研究,但其稳定性相对较差限制了实际应用。本研究以二氰基氧化呋咱为原料,通过还原-肟化-环化缩合反应将氧化呋咱替换为呋咱结构,合成了稳定性更高的新型1,2,5-噁二唑桥联双1,2,4-噁二唑含能化合物(1),对其硝化后得到3-(4-(5-氨基-1,2,4-噁二唑-3-基)-1,2,5-噁二唑-3-基)-1,2,4-噁二唑-5(4H)-酮(2)。利用核磁共振(NMR)、元素分析(EA)和红外光谱(IR)对其进行了表征。此外,采用单晶X射线衍射法进一步验证了化合物的准确结构,其中化合物1为斜方晶系,Pbcn空间群,Z=4, ρ=1.825 g·cm-3,化合物2·3H₂O为三斜晶系,P-1空间群,Z=2,ρ=1.641 g·cm-3。化合物1和2的撞击感度均为40 J,摩擦感度为360 N,计算爆速分别为7921 m·s-1和7660 m·s-1,计算爆压分别为22.4 GPa和20.5 GPa,均高于传统炸药TNT(6881 m·s-1,19.5 GPa)。

    Abstract:

    Furoxan has been extensively studied due to its high energy provided by potential “nitro” fragment, but the relatively poor stability limits its practical applications. A novel energetic compound, 3,3''-(1,2,5-oxadiazole-3,4-diyl)bis(1,2,4-oxadiazol-5-amine)(1), was synthesized from dicyanofuroxan via a three-step procedure involving reduction, oximation, and cyclization-dehydration reactions. Subsequent nitration of 1 afforded 3-(4-(5-amino-1,2,4-oxadiazol-3-yl)-1,2,5-oxadiazol-3-yl)-1,2,4-oxadiazol-5(4H)-one(2). The structures of both compounds were characterized by nuclear magnetic resonance (NMR) spectroscopy, elemental analysis (EA), infrared (IR) spectroscopy, and single crystal X-ray diffraction analyses. Results show that compound 1 crystallizes in orthorhombic crystal system, space group Pbcn, Z = 4, with a crystal density of 1.825 g·cm⁻³. The trihydrate of compound 2·3H₂O crystallizes in triclinic crystal system, space group P1, Z = 2, with a crystal density of 1.641 g·cm-3 Both compounds exhibit high insensitivity to mechanical stimuli, with impact sensitivity >40 J and friction sensitivity >360 N. Their calculated detonation velocity (7921 m·s-1 for 1 and 7660 m·s-1 for 2) and detonation pressure (22.4 GPa for 1 and 20.5 GPa for 2) are superior to those of TNT (6881 m·s-1, 19.5 GPa).

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朱腾,唐杰,程广斌,等.1,2,5-噁二唑桥联双1,2,4-噁二唑化合物的合成及性能[J].含能材料, 2026, 34(3):241-248. DOI:10.11943/CJEM2025231.
ZHU Teng, TANG Jie, CHENG Guang-bin, et al. Synthesis and Properties of Energetic Compounds Based on 1,2,5-Oxadiazole-bridged Bis(1,2,4-oxadiazole)[J]. Chinese Journal of Energetic Materials, 2026, 34(3):241-248. DOI:10.11943/CJEM2025231.

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  • 收稿日期: 2025-10-15
  • 最后修改日期: 2026-02-04
  • 录用日期: 2026-01-26
  • 在线发布日期: 2026-02-04
  • 出版日期: 2026-03-25