Thermally Stable Energetic Salts Featuring Tetrazine-Derived Diammonium Cations and Nitrogen-Rich Energetic Anions

A nitrogen-rich tetrazine-based dicationic precursor, (1,2,4,5-tetrazine-3,6-diyl)dimethanaminium chloride (3), was synthesized in an efficient three-step procedure from readily available starting materials. Subsequent pairing of 3 with a series of nitrogen- and oxygen-rich energetic anions afforded energetic salts (4–12) that exhibit high detonation performance, good thermal stability, and reduced mechanical sensitivity. Among all the compounds, 9 exhibited the most favorable balance between energetic performance (Vd = 8533 m s–1; P = 27.09 GPa) and stability (Td = 207 °C; IS = 12.5 J), with energetic performance comparable to that of the well-known explosive RDX. Overall, these results demonstrate that tetrazine-derived diamine cations provide a promising platform for the development of thermally stable energetic salts with balanced energetic performance and stability.