A novel method to synthesize stable nitrogen-rich polynitrobenzenes with π-stacking for high-energy-density energetic materials

Two nitrogen-rich energetic compounds with π-stacking, 1,1′-dichloro-2,2′,3,3′,6,6′-hexanitro-5,5′-dihydroxyazobenzene (1) and 8-(2,4,6-triazido-3,5-dinitrophenyl)-8H-[1,2,3]triazolo[4′,5′:5,6]benzo[1,2-c:3,4-c′]bis([1,2,5]oxadiazole) 1,4-dioxide (2), were prepared by a novel synthesis method, and their structures were determined by single-crystal X-ray diffraction analysis. The decomposition temperature of 1 is 336 °C and 2 exhibits excellent heat of formation of 1160.5 kJ mol⁻¹ (2.21 kJ g⁻¹). The condensation reaction of the coupling of a N═N bond and an azido from 1 to 2 was proved to be an efficient method to synthesize benzotriazole. This synthetic strategy for benzotriazole may arouse considerable interest in the area of organic synthesis.