C6N10O4: Thermally Stable Nitrogen-Rich Inner Bis(diazonium) Zwitterions.

Two nitrogen-rich inner bis(diazonium) salts, the 4,4'-dinitro-5,5'-diazo-2,2'-bisimidazole (2) and the 4,4'-dinitro-5,5'-diazo-3,3'-bispyrazole (4) zwitterions, are described. Compound 2 was synthesized unexpectedly from the nitration of 4,4'-dinitro-5,5'-diamino-1H,1'H-2,2'-bisimidazole (1) in a mixture of trifluoroacetic anhydride and 100% nitric acid. Both 2 and 4 show good thermal stability, especially 2 has a decomposition temperature of 199 °C, which is the highest one in any of the reported hydrogen-free nitrogen-rich diazonium salts.