The evolution of energetic materials science presents new challenging tasks associated with the creation of advanced technologies for sustainable development of the future. In this work, a set of new heat-resistant high-energy materials incorporating the polynitrophenyl-1,2,5-oxadiazole scaffold enriched with azo/azoxy moieties have been designed and synthesized. Due to a smart combination of explosophoric groups and 1,2,5-oxadiazole rings, the prepared high-energy substances have excellent thermal stability (up to 300 °C), good densities (up to 1.75 g cm^–3), high enthalpies of formation (340–538 kJ mol^–1), and high combined nitrogen–oxygen content (63–68%). In-depth structural analysis revealed the presence of strong intra- and intermolecular hydrogen bonds in aminodinitrophenyl derivatives, which in combination with the small deviation of electrostatic potential values explains the low mechanical sensitivity of these materials. At the same time, trinitrophenyl-1,2,5-oxadiazoles incorporating three adjacent non-coplanar nitro groups demonstrated higher sensitivity to impact, albeit retaining complete insensitivity to friction. The overall performance of the thus prepared high-energy substances exceeds that of the known heat-resistant explosive hexanitrostilbene. Therefore, the newly synthesized family of energetic polynitrophenyl-1,2,5-oxadiazoles provides a fruitful foundation for the creation of the advanced heat-resistant energetic materials of the future.

中文翻译：

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偶氮双（聚硝基苯基-1,2,5-恶二唑）作为耐热摩擦不敏感的高能材料


能量材料科学的发展提出了新的具有挑战性的任务，这些任务与为未来可持续发展创造先进技术相关。在这项工作中，设计并合成了一组新型耐热高能材料，其中掺入了富含偶氮/嘧氧基团的聚硝基苯基-1,2,5-噁二唑支架。由于爆炸基团和 1,2,5-恶二唑环的巧妙结合，所制备的高能物质具有优异的热稳定性（高达 300 °C）、良好的密度（高达 1.75 g cm^–3）、高生成焓 （340–538 kJ mol^–1） 和高结合氮氧含量 （63–68%）。深入的结构分析揭示了氨基二硝基苯基衍生物中存在强分子内和分子间氢键，这与静电电位值的微小偏差相结合，解释了这些材料的低机械灵敏度。同时，掺入三个相邻非共面硝基的三硝基苯基-1,2,5-恶二唑表现出更高的冲击敏感性，尽管对摩擦完全不敏感。由此制备的高能物质的整体性能超过了已知的耐热爆炸物六硝基芪。因此，新合成的含能聚硝基苯基-1,2,5-恶二唑家族为创造未来先进的耐热含能材料奠定了丰硕的基础。