Two-step construction of a tricyclic energetic precursor towards dinitramine-functionalized high-energy materials

This work employed a two-step strategy for the efficient construction of tricyclic energetic compound. Subsequent functionalization of the amino groups successfully afforded the polynitro energetic derivatives PTO-2 and PTO-3. Among them, tricyclic dinitroamino compound PTO-3 (ρ = 1.88 g cm −3 , D V = 9105 m s −1 , T d = 114 °C, IS = 18 J) exhibits outstanding detonation performance, achieving remarkable overall properties among tricyclic dinitroamino energetic compounds. The salt-forming reaction of PTO-3 yielded triionic energetic salts, a seldom reported result. The triammonium salt 4 (T d = 201 °C) and trihydrazinium salt 5 (T d = 183 °C) display a marked enhancement in thermal stability relative to PTO-3, with their decomposition temperatures elevated by more than 69 °C. Compounds PTO-3, 4 and 5 exhibit superior detonation performance (D V > 8982 m s −1 , P > 34.4 GPa) compared to RDX (D V = 8795 m s −1 , P = 34.9 GPa). This study provides a novel insight into the synthesis of tricyclic energetic compounds and is expected to facilitate the development of new high-energy low-sensitivity energetic materials. • A tricyclic energetic compound was efficiently constructed via a two-step strategy. • PTO-3 and its salts achieve a balance between energy and sensitivity. • Triionic energetic salt 5 outperforms HMX in both detonation velocity and safety.