Derivatives of 3,6-Bis(3-aminofurazan-4-ylamino)-1,2,4,5-tetrazine: Excellent Energetic Properties with Lower Sensitivities.

To find a balance between energy and safety, a series of compounds based on azo-, azoxy-, 1,4,2,5-dioxadiazene-, and 3,6-diamino-1,2,4,5-tetrazine-bridged bis(aminofurazan) were designed and synthesized. These compounds were analyzed by nitro group charges (Qnitro) and bond dissociation energy (BDE) calculations, which are related to sensitivity and stability. Based on the calculated results, derivatives of 3,6-bis(3-aminofurazan-4-ylamino)-1,2,4,5-tetrazine have the largest values for -Qnitro and BDE of all of the bis(aminofurazan) compounds. This shows that compounds based on 3,6-bis(3-aminofurazan-4-ylamino)-1,2,4,5-tetrazine have the lowest sensitivities and best stabilities, which has been substantiated by experiments. Additionally, their explosive properties remain essentially competitive with compounds based on azo-, azoxy-, and 1,4,2,5-dioxadiazene-bridged bis(aminofurazan). Hirshfeld surface calculations were also performed to better understand the relationship between the molecular structure and stability/sensitivity. This work highlights the value of 3,6-diamino-1,2,4,5-tetrazine as a linker to achieve good balance between safety and energy.