Ilya D. Deltsov, , , Dmitry B. Vinogradov, , , Konstantin A. Monogarov, , and , Leonid L. Fershtat*,
{"title":"恶二唑与氨基二硝基苯支架的联盟:通往耐热摩擦不敏感的含能材料。","authors":"Ilya D. Deltsov, , , Dmitry B. Vinogradov, , , Konstantin A. Monogarov, , and , Leonid L. Fershtat*, ","doi":"10.1021/acs.orglett.5c03404","DOIUrl":null,"url":null,"abstract":"<p >A set of new energetic materials composed of 1,2,5-oxadiazole moieties coupled with the 4-amino-3,5-dinitrophenyl scaffold through the 1,2,4-oxadiazole linker was designed and synthesized. Synthesized energetic substances exhibit high densities (1.66–1.74 g cm<sup>–3</sup>), positive enthalpies of formation (17–572 kJ mol<sup>–1</sup>), and high combined nitrogen–oxygen content (61–67%). Advantageously, newly prepared materials showed high thermal stability (up to 251 °C) and complete insensitivity to friction while retaining good detonation velocities (6.9–7.2 km s<sup>–1</sup>). Overall, fine modulation of oxadiazole and nitroaromatic scaffolds represents a good strategy for an assembly of balanced and heat-resistant energetic materials.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"27 39","pages":"11033–11037"},"PeriodicalIF":5.0000,"publicationDate":"2025-09-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Oxadiazole Alliance with an Aminodinitrophenyl Scaffold: En Route to Heat-Resistant Friction-Insensitive Energetic Materials\",\"authors\":\"Ilya D. Deltsov, , , Dmitry B. Vinogradov, , , Konstantin A. Monogarov, , and , Leonid L. Fershtat*, \",\"doi\":\"10.1021/acs.orglett.5c03404\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p >A set of new energetic materials composed of 1,2,5-oxadiazole moieties coupled with the 4-amino-3,5-dinitrophenyl scaffold through the 1,2,4-oxadiazole linker was designed and synthesized. Synthesized energetic substances exhibit high densities (1.66–1.74 g cm<sup>–3</sup>), positive enthalpies of formation (17–572 kJ mol<sup>–1</sup>), and high combined nitrogen–oxygen content (61–67%). Advantageously, newly prepared materials showed high thermal stability (up to 251 °C) and complete insensitivity to friction while retaining good detonation velocities (6.9–7.2 km s<sup>–1</sup>). Overall, fine modulation of oxadiazole and nitroaromatic scaffolds represents a good strategy for an assembly of balanced and heat-resistant energetic materials.</p>\",\"PeriodicalId\":54,\"journal\":{\"name\":\"Organic Letters\",\"volume\":\"27 39\",\"pages\":\"11033–11037\"},\"PeriodicalIF\":5.0000,\"publicationDate\":\"2025-09-19\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Organic Letters\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://pubs.acs.org/doi/10.1021/acs.orglett.5c03404\",\"RegionNum\":1,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Letters","FirstCategoryId":"92","ListUrlMain":"https://pubs.acs.org/doi/10.1021/acs.orglett.5c03404","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
摘要
设计并合成了一组由1,2,5-恶二唑基团通过1,2,4-恶二唑连接剂与4-氨基-3,5-二硝基苯支架偶联而成的新型含能材料。合成的含能物质具有高密度(1.66 ~ 1.74 g cm-3)、正生成焓(17 ~ 572 kJ mol-1)和高氮氧结合含量(61 ~ 67%)的特点。有利的是,新制备的材料具有高热稳定性(高达251°C)和对摩擦完全不敏感,同时保持良好的爆轰速度(6.9-7.2 km s-1)。总的来说,对恶二唑和硝基芳香支架进行精细调节是一种组装平衡和耐热含能材料的良好策略。
Oxadiazole Alliance with an Aminodinitrophenyl Scaffold: En Route to Heat-Resistant Friction-Insensitive Energetic Materials
A set of new energetic materials composed of 1,2,5-oxadiazole moieties coupled with the 4-amino-3,5-dinitrophenyl scaffold through the 1,2,4-oxadiazole linker was designed and synthesized. Synthesized energetic substances exhibit high densities (1.66–1.74 g cm–3), positive enthalpies of formation (17–572 kJ mol–1), and high combined nitrogen–oxygen content (61–67%). Advantageously, newly prepared materials showed high thermal stability (up to 251 °C) and complete insensitivity to friction while retaining good detonation velocities (6.9–7.2 km s–1). Overall, fine modulation of oxadiazole and nitroaromatic scaffolds represents a good strategy for an assembly of balanced and heat-resistant energetic materials.
期刊介绍:
Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.