The Stabilization of High-Nitrogen Systems: 10 Catenated Nitrogen Chain

High-nitrogen materials have attracted intense interest in recent decades due to their unique chemical, physical, and biological properties. Stabilizing high-nitrogen materials is often challenging as they become more unstable with increasing nitrogen catenation and nitrogen mass percentage increase.  Although approaches such as introducing alternating positive/negative charges and restricting electrocyclic N₂ loss have been reported for stabilizing high-nitrogen systems, these structural motifs have not previously been applied to highly catenated nitrogen chains. Accordingly, we sought to design a new highly catenated nitrogen chain with the aforementioned considerations, which began with the synthesis of 1,5-diamino-3-methyl-tetrazolium chloride. When 1,5-diamino-3-methyl-tetrazolium chloride is reacted with white fuming nitric acid, a novel 10-catenated nitrogen chain in 1,1'-azobis-3,3'-dimethyl-5,5'-diamino-tetrazol-3,3'-ium dinitrate is afforded. Physical and chemical properties of this exotic material are described herein, and implications for high-nitrogen material design are discussed.