A strategy for stabilizing of N8 type energetic materials by introducing 4-Nitro-1,2,3-Triazole scaffolds

Abstract

A series of multi-functionalized 4-nitro-1,2,3-triazole based C–N linked biheterocyclic energetic compounds were synthesized using CDI (1,1′-carbonyldiimidazole) induced dehydrative cyclization. Among these energetic analogues, the representative compounds 2 and 6 exhibit great potential as melt-castable explosive (2: Tm = 72 °C , Td = 231 °C) and high-performance insensitive energetic material (6: d = 1.82 g cm−3, D = 8688 m s−1, IS > 40 J), respectively. More importantly, employing THA (O-tosylhydroxylamine) and SDIC(sodium dichloroisocyanurate), functionalized N8-branched compound (F-N8B, (E)-1,2-bis(4,5′-dinitro-2′H-[2,4′-bi(1,2,3-triazol)]-2′-yl)diazene) was synthesized via N-amination and oxidative azo coupling. In comparison to previously reported N8 type of energetic compounds, F-N8B exhibits improved impact sensitivity and friction sensitivity (IS = 7 J, FS = 72 N).