Unsymmetrical functionalization
of bis-1,2,4-triazoles was attempted,
and a series of nitrogen/oxygen-rich energetic materials were designed
and synthesized in this study. Compared with previously reported symmetrical
bis-1,2,4-triazole derivatives (iv and v), both unsymmetrically functionalized bis-1,2,4-triazole derivatives
(3 and 7) in this work possess improved
safety properties (impact sensitivities: 22 J (3) and
11 J (7); friction sensitivities: >360 N (3) and 250 N (7)). Meanwhile, the detonation performance
of 3 was apparently improved compared with the C-nitrated compound iv. These features indicate
that unsymmetrical functionalization would be a favorable strategy
to construct energetic materials with both high energy and safety.
Moreover, N-trinitromethyl-functionalized compound 5 possesses high density (1.92 g cm–3),
positive oxygen balance (+25.1%), and desirable detonation performance
similar to HMX, with higher specific impulse (I
sp = 265.1 s) than ADN, suggesting its superiority as a highly
energetic oxidizer.