Functionalized planar aromatic rings as precursors to energetic N,N′-(4,6-dinitro-1,3-phenylene)dinitramide and its salts

Abstract

Functionalization of planar aromatic rings is very straightforward, up scalable, and economical in comparison with many azole, caged, linear or cyclic structures. In our present work, a facile synthesis of...

Design of N–N ylide bond-based high energy density materials: a theoretical survey

“…The density functional theory method (DFT) is a powerful tool for studying the structures and energetic properties of energetic materials. [22][23][24] The electronic structures, heats of formation, thermal stabilities, and impact sensitivities were studied by DFT using the Gaussian 09 (ref. 25) program packages.…”

The combined effect of pyrazole and amino groups: preparation of novel energetic coordination compounds with high ClO4− content

“…1,2 Due to the simple preparation methods, wide availability of raw materials, and excellent explosion performance, ionic salts have become a research hotspot. [3][4][5] Specifically, unlike tetrazole and tetrazine, the pyrazole ring can be protonated to prepare ionic salts due to its basicity, which has been developed by many researchers. [6][7][8] It is precisely because of the special characteristic that even if its derivative groups contain [H + ] which is easily ionizable, it can still be prepared into an ionic salt, such as DAPOP (3,5-diamino-4H-pyrazol-4-one oxime perchlorate salt) 9 (shown in Scheme 1, Path 1a).…”

“…[6][7][8] It is precisely because of the special characteristic that even if its derivative groups contain [H + ] which is easily ionizable, it can still be prepared into an ionic salt, such as DAPOP (3,5-diamino-4H-pyrazol-4-one oxime perchlorate salt) 9 (shown in Scheme 1, Path 1a). In addition, even if pyrazole forms multiple fused rings with tetrazine or triazole, this characteristic remains unchanged because the binding site for [H + ] is still on the pyrazole skeleton, such as DATTP (3,6diamino-1,2,4-triazolo [4,3-b]tetrazine perchlorate salt) and FTP ( [1,2,4]triazolo[4′,3′:1,5]- [1,2,4]triazolo [3,4-f] [1,2,4]triazolo [1,5-d] [1,2,4]triazine-2,5,10-triamine perchlorate salt) 10,11 (shown in Scheme 1, Path 1b and 1c). However, due to the limited ability of the pyrazole skeleton it can only bind one equivalent of [H + ], so the ratio of the organic skeleton to [ClO 4 − ] is only 1 : 1.…”

Synthesis and detonation performance of novel tetrazolyl–triazine nitrogen-rich energetic materials

“…Such heterocycles also allow selective structural modification through judicious choice of substituents. [15][16][17][18][19][20][21] Furthermore, many N-rich heterocycles such as imidazole, triazole, or tetrazole possess N atoms that have an acidic proton, which may be easily removed in the presence of a base, thereby yielding an anionic species. When combined with appropriate cationic species, energetic organic salts may be isolated.…”