C–C bonded bis-5,6 fused triazole–triazine compound: an advanced heat-resistant explosive with high energy and low sensitivity

It is still an urgent problem in the field of energetic materials to explore the synthesis of heat-resistant compounds with balanced energy and thermal stability through simple synthetic routes. Recently, fused compounds are considered to provide a promising framework for the construction of ideal heat-resistant compounds. In this study, three novel C-C bonded bis-5,6 fused triazole-triazine compounds, 3,3'-dinitro-[7,7'-bi[1,2,4]triazolo[5,1-c][1,2,4]triazine]-4,4'-diamine (2), 4,4'-diamino-[7,7'-bi[1,2,4]triazolo[5,1-c][1,2,4]triazine]-3,3'-dicarbonitrile (3), and 3,3'-di(1H-tetrazol-5-yl)-[7,7'-bi[1,2,4]triazolo[5,1-c][1,2,4]triazine]-4,4'-diamine (4), were synthesized by a simple method. Compound 2 exhibited an approaching detonation velocity of 8837 m s-1 compared with that of the traditional high energy explosive RDX velocity of 8795 m s-1, while its thermal stability (Td = 327 °C) was comparable to that of the heat-resistant explosive HNS (Td = 318 °C). At the same time, the double fused compound 2 also realized high density (1.90 g cm-3) and extremely low sensitivity (FS > 360 N, IS > 40 J). The above good comprehensive properties prove that compound 2 can be used as a potential insensitive high-energy heat-resistant explosive. In addition, the effects of the crystal structure on the sensitivity and thermal stability were studied using the quantum chemical methods. These results imply that the formation of double fused ring compounds by the ring closing reaction at symmetrical positions is an ideal strategy for the development of advanced heat-resistant explosives.