Enforced Planar FOX-7-like Molecules: A Strategy for Thermally Stable and Insensitive π-Conjugated Energetic Materials,Journal of the American Chemical Society

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Enforced Planar FOX-7-like Molecules: A Strategy for Thermally Stable and Insensitive π-Conjugated Energetic Materials
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2020-03-31 , DOI: 10.1021/jacs.0c01640
Yongxing Tang _{1,

2} , Wei Huang ₁ , Gregory H. Imler ₃ , Damon A. Parrish ₃ , Jean’ne M. Shreeve ₂

Affiliation

Exploring new energetic derivatives of 1,1-diamino-2,2-dinitroethylene (FOX-7) is still a key aspect in the ﬁeld of energetic materials. However, so far most of the attention has been focused on modification of FOX-7 via different reaction strategies. Now we report the design of three new FOX-7-like compounds (3-5) where one nitro group in FOX-7 is replaced by a nitrogen-rich heterocyclic ring. Each of them is characterized by single-crystal X-ray crystallography. Electronic structures are studied through computational methods in comparison with FOX-7. In addition, the chemical reactivity of 3 was also investigated. Its hydroxylammonium (7), hydrazinium (8), and ammonium (9) salts were prepared and the nitrate product (10) was also isolated. Compound 10 has a C-N bond length of 1.577 Å that is one of the longest values found for the C-NO2 bond. It was found that the incorporation of a tetrazole or triazole ring into the backbone of a conjugated nitroenamine does lead to a planar structure, which not only enhances the thermal stability but also improves the sensitivity of the product.

中文翻译：

强制平面 FOX-7 样分子：热稳定和不敏感的 π 共轭高能材料的策略

探索 1,1-二氨基-2,2-二硝基乙烯 (FOX-7) 的新高能衍生物仍然是高能材料领域的一个关键方面。然而，到目前为止，大部分注意力都集中在通过不同反应策略对 FOX-7 的修饰上。现在我们报告了三种新的 FOX-7 类化合物 (3-5) 的设计，其中 FOX-7 中的一个硝基被富氮杂环取代。它们中的每一个都以单晶 X 射线晶体学为特征。与 FOX-7 相比，通过计算方法研究电子结构。此外，还研究了3的化学反应性。制备了其羟铵 (7)、肼 (8) 和铵 (9) 盐，并分离出硝酸盐产物 (10)。化合物 10 的 CN 键长为 1.577 Å，这是 C-NO2 键的最长值之一。

更新日期：2020-03-31

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