Besides the well-known pyrotechnic applications of insensitive high energy compounds such as s-tetrazine, they are promising materials for relevant applications (e.g., electrochemical energy storage, photocatalysis). Bis-3,5-diamino-1,2,4-triazolyl-1,2,4,5-tetrazine (BDTT) is a nitrogen-rich conjugated heterocyclic compound (nitrogen ≈ 71 wt %), inert to ignition and mechanical stimuli and thermally stable up to 370 °C. The solvent-free crystalline structure of this high energy density compound (named IEF-12 for IMDEA energy framework) is reported here for the first time using the high resolution powder X-ray diffraction (PXRD) and ¹H, ¹³C, and ¹⁵N solid state nuclear magnetic resonance (NMR) spectroscopy. We demonstrate that IEF-12 has features of a small molecule organic semiconductor, namely, lamellar π-stacked crystal packing in the solid state, a low energy optical bandgap E_g^opt = 2.27 eV, and a relatively high value of dielectric constant ε_r = 4.86. Overall, we demonstrated on IEF-12 that insensitive high energy density materials (HEDM) may open an avenue for nonclassically structured organic semiconductors, paving the way for optoelectronic and photovoltaic applications.

中文翻译：

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Bis-3,5-Diamino-1,2,4-Triazolyl-1,2,4,5-Tetrazine：从不敏感的高能量密度材料到小分子有机半导体

除了不敏感的高能化合物（例如s-四嗪）的众所周知的烟火应用外，它们还是用于相关应用（例如电化学能量存储，光催化）的有前途的材料。Bis-3,5-二氨基-1,2,4-三唑基-1,2,4,5-四嗪（BDTT）是一种富氮共轭杂环化合物（氮≈71 wt％），对点火和机械刺激呈惰性并在高达370°C的温度下具有热稳定性。本文首次使用高分辨率粉末X射线衍射（PXRD）和¹ H，¹³ C和^15记录了这种高能量密度化合物的无溶剂晶体结构（在IMDEA能量框架中命名为IEF-12）。N固态核磁共振（NMR）光谱。我们证明IEF-12具有小分子有机半导体的特征，即固态的层状π堆叠晶体堆积，低能带隙E _g ^opt = 2.27 eV和相对较高的介电常数_εr = 4.86。总体而言，我们在IEF-12上证明了不敏感的高能量密度材料（HEDM）可能为非经典结构的有机半导体开辟一条道路，为光电和光伏应用铺平了道路。