Selecting Suitable Substituents for Energetic Materials Based on a Fused Triazolo-[1,2,4,5]tetrazine Ring

The
more energetic substituent introduced, such as nitramino, nitro,
azido, and N-oxide group, the better the detonation performance but
the lower the stability of the compounds obtained. In order to synthesize
energetic materials that display both high detonation performance
and low sensitivity, it is useful to understand how those energetic
groups affect material properties. The syntheses of some materials
based on the triazolo-[1,2,4,5]­tetrazine fused ring that contain combinations
of different energetic groups are described. For the first time, a
fused ring containing the nitramino and the N-oxide groups was synthesized
(3). Compound 3 and its salts exhibit high
densities (>1.82 g cm–3) and detonation performances
(>9047 m s–1, > 34.7 GPa) as well as acceptable
sensitivities. As a result of hydrogen bonding, the hydrazinium salt
(3b) has a density of 1.83 g cm–3,
with a high detonation velocity (9470 m s–1) and
reasonable sensitivities (12 J, 120 N) which is superior to CL-20.
Comparisons are made with our previously reported materials in order
to demonstrate how energetic substituents affect properties.