The skeleton of 5,7-fused bicyclic imidazole-diazepine for heat-resistant energetic materials

In light of the low yields and complex reaction routes of some well-known 5,5-fused and 5,6-fused bicyclic compounds, a series of 5,7-fused bicyclic imidazole-diazepine compounds were developed with high yields by only two efficient steps. Significantly, the seven-membered heterocyclic ring has a stable energetic skeleton with multiple modifiable sites. However, the 5,7-fused bicyclic energetic compounds were rarely reported in the area of energetic materials. Three neutral compounds 1, 2 and 4 were synthesized in this work. To improve the detonation performances of the 5,7-fused neutral compounds, corresponding perchlorate 1a and 2a were further developed. The physicochemical and energetic performances of all newly developed compounds were experimentally determined. All newly prepared energetic compounds exhibit high decomposition temperatures (T-d: 243.8-336 degrees C) and low mechanical sensitivities (IS: >15 J, FS: >280 N). Among them, the velocities performances of 1a (D-v = 7651 m/s) and 4 (D-v = 7600 m/s) are comparable to that of typical heat-resistant energetic material HNS (D-v = 7612 m/s). Meanwhile, the high decomposition temperature and low mechanical sensitivities (T-d = 336 degrees C; IS = 32 J; FS > 353 N) of 4 are superior to that of HNS (T-d = 318 degrees C; IS = 5 J; FS = 250 N). Hence, the 5,7-fused bicyclic compounds with high thermostability, low sensitivities and adjustable detonation performance have a clear tendency to open up a new space for the development of heat-resistant energetic materials.(c) 2022 China Ordnance Society. Publishing services by Elsevier B.V. on behalf of KeAi CommunicationsCo. Ltd. This is an open access article under the CC BY-NC-ND license

Automated summary

A series of 5,7-fused bicyclic imidazole-diazepine compounds were developed with high yields by only two efficient steps. These compounds have a stable energetic skeleton with multiple modifiable sites, exhibiting high decomposition temperatures and low mechanical sensitivities. Among them, compound 4 has superior thermochemical stability and mechanical sensitivities compared to a typical heat-resistant energetic material.