A π-Stacked Highly Stable, Insensitive, Energy-Containing Material with a Useful Planar Structure

pi-Stacking is common in materials, but different pi-pi stacking modes remarkably affect the properties and performances of materials. In particular, weak interactions, pi-stacking and hydrogen bonding often have a significant impact on the stability and sensitivity of high-energetic compounds. A fused [5,7,5]-tricyclic energetic compound with a conjugated structure has been designed and synthesized. 4 H -[1,2,5]Oxadiazolo[3,4- e ][1,2,4]triazolo[3,4- g ][1,2,4]triazepin-8-amine is obtained in 48% yield from 3-amino-4-carboxy-1,2,5-oxadiazole through an efficient two-step reaction. Owing to its layered planar structure and weak pi interactions between layers, 4 H -[1,2,5]oxadiazolo[3,4- e ][1,2,4]triazolo[3,4- g ][1,2,4]triazepin-8-amine exhibits high thermal stability ( T-d = 318 degrees C), low sensitivity ( IS = 40 J, FS = 360 N), and relatively excellent detonation performance ( D = 7059 ms (-1) , P = 20.2 GPa). This detonation performance is superior to that of the conventional explosive TNT. The developed procedure provides a new method for the synthesis of fused ring compounds.