Shreyasi Banik, Navaneet Kumar, Vikas D. Ghule, Srinivas Dharavath
{"title":"高能材料的骨架编辑:通过 Nef 反应,酸催化一步合成桥式三唑类高能量密度材料","authors":"Shreyasi Banik, Navaneet Kumar, Vikas D. Ghule, Srinivas Dharavath","doi":"10.1021/acsami.4c16858","DOIUrl":null,"url":null,"abstract":"Thermally stable insensitive energetic materials have captivated significant attention from the global research community due to their potential impact. In this study, a series of symmetric and asymmetric nitromethyl-bridged triazole compounds were synthesized from pyrimidine moieties via a skeletal editing approach. Additionally, carbonyl-bridged compounds were synthesized in a single step by using acid-catalyzed Nef reactions from their nitromethyl precursors. Peripheral modifications of pyrimidine resulted in fused energetic moieties. All synthesized compounds were fully characterized by using infrared spectroscopy, high-resolution mass spectrometry, multinuclear magnetic resonance spectroscopy, elemental analysis, and differential scanning calorimetry. Single-crystal X-ray diffraction analysis confirmed the structures of compounds <b>4</b> and <b>10</b>. The newly synthesized moieties exhibit densities ranging from 1.75 to 1.86 g cm<sup>–3</sup>, detonation velocities between 8044 and 8608 m s<sup>–1</sup>, and detonation pressures between 23.10 and 30.31 GPa. Notably, compounds <b>9</b> and <b>10</b> demonstrate exceptional heat resistance, with decomposition temperatures of 315 and 335 °C, respectively. Computational studies, including density functional theory, quantum theory of atoms in molecules, noncovalent interactions, and electrostatic surface potential analysis, account for hydrogen-bonding and noncovalent interactions. This work highlights the potential of skeletal editing in the development of high-performing, thermally stable energetic materials.","PeriodicalId":5,"journal":{"name":"ACS Applied Materials & Interfaces","volume":"11 1","pages":""},"PeriodicalIF":8.3000,"publicationDate":"2024-11-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Skeletal Editing of Energetic Materials: Acid-Catalyzed One-Step Synthesis of Bridged Triazoles as High-Energy-Density Materials via the Nef Reaction\",\"authors\":\"Shreyasi Banik, Navaneet Kumar, Vikas D. Ghule, Srinivas Dharavath\",\"doi\":\"10.1021/acsami.4c16858\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"Thermally stable insensitive energetic materials have captivated significant attention from the global research community due to their potential impact. In this study, a series of symmetric and asymmetric nitromethyl-bridged triazole compounds were synthesized from pyrimidine moieties via a skeletal editing approach. Additionally, carbonyl-bridged compounds were synthesized in a single step by using acid-catalyzed Nef reactions from their nitromethyl precursors. Peripheral modifications of pyrimidine resulted in fused energetic moieties. All synthesized compounds were fully characterized by using infrared spectroscopy, high-resolution mass spectrometry, multinuclear magnetic resonance spectroscopy, elemental analysis, and differential scanning calorimetry. Single-crystal X-ray diffraction analysis confirmed the structures of compounds <b>4</b> and <b>10</b>. The newly synthesized moieties exhibit densities ranging from 1.75 to 1.86 g cm<sup>–3</sup>, detonation velocities between 8044 and 8608 m s<sup>–1</sup>, and detonation pressures between 23.10 and 30.31 GPa. Notably, compounds <b>9</b> and <b>10</b> demonstrate exceptional heat resistance, with decomposition temperatures of 315 and 335 °C, respectively. Computational studies, including density functional theory, quantum theory of atoms in molecules, noncovalent interactions, and electrostatic surface potential analysis, account for hydrogen-bonding and noncovalent interactions. This work highlights the potential of skeletal editing in the development of high-performing, thermally stable energetic materials.\",\"PeriodicalId\":5,\"journal\":{\"name\":\"ACS Applied Materials & Interfaces\",\"volume\":\"11 1\",\"pages\":\"\"},\"PeriodicalIF\":8.3000,\"publicationDate\":\"2024-11-13\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"ACS Applied Materials & Interfaces\",\"FirstCategoryId\":\"88\",\"ListUrlMain\":\"https://doi.org/10.1021/acsami.4c16858\",\"RegionNum\":2,\"RegionCategory\":\"材料科学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"MATERIALS SCIENCE, MULTIDISCIPLINARY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"ACS Applied Materials & Interfaces","FirstCategoryId":"88","ListUrlMain":"https://doi.org/10.1021/acsami.4c16858","RegionNum":2,"RegionCategory":"材料科学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"MATERIALS SCIENCE, MULTIDISCIPLINARY","Score":null,"Total":0}
Skeletal Editing of Energetic Materials: Acid-Catalyzed One-Step Synthesis of Bridged Triazoles as High-Energy-Density Materials via the Nef Reaction
Thermally stable insensitive energetic materials have captivated significant attention from the global research community due to their potential impact. In this study, a series of symmetric and asymmetric nitromethyl-bridged triazole compounds were synthesized from pyrimidine moieties via a skeletal editing approach. Additionally, carbonyl-bridged compounds were synthesized in a single step by using acid-catalyzed Nef reactions from their nitromethyl precursors. Peripheral modifications of pyrimidine resulted in fused energetic moieties. All synthesized compounds were fully characterized by using infrared spectroscopy, high-resolution mass spectrometry, multinuclear magnetic resonance spectroscopy, elemental analysis, and differential scanning calorimetry. Single-crystal X-ray diffraction analysis confirmed the structures of compounds 4 and 10. The newly synthesized moieties exhibit densities ranging from 1.75 to 1.86 g cm–3, detonation velocities between 8044 and 8608 m s–1, and detonation pressures between 23.10 and 30.31 GPa. Notably, compounds 9 and 10 demonstrate exceptional heat resistance, with decomposition temperatures of 315 and 335 °C, respectively. Computational studies, including density functional theory, quantum theory of atoms in molecules, noncovalent interactions, and electrostatic surface potential analysis, account for hydrogen-bonding and noncovalent interactions. This work highlights the potential of skeletal editing in the development of high-performing, thermally stable energetic materials.
期刊介绍:
ACS Applied Materials & Interfaces is a leading interdisciplinary journal that brings together chemists, engineers, physicists, and biologists to explore the development and utilization of newly-discovered materials and interfacial processes for specific applications. Our journal has experienced remarkable growth since its establishment in 2009, both in terms of the number of articles published and the impact of the research showcased. We are proud to foster a truly global community, with the majority of published articles originating from outside the United States, reflecting the rapid growth of applied research worldwide.