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Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Interaction of Nitrogen-Rich Cations with Azotriazolone Anions through Ion Exchange Results in the Formation of
Mingzhen Xie1, Tianlong Zhou1, Bozhou Wang2
1School of Materials and Chemistry, Southwest University of Science and Technology, Mianyang 621010, P. R. China.
Abstract:
In our pursuit of promoting the green development of energetic materials and harnessing their functional benefits, we strive to address the inherent contradiction between energy and low sensitivity. In this regard, we have successfully constructed an azotriazole framework via environmentally friendly electrochemistry with a satisfactory yield of 62.3%. Through a simple ion-exchange process, we then synthesized nitrogen-rich salt derivatives of azotriazolone. These nitrogen-rich salts exhibit a wide range of nitrogen contents, ranging from 32.16 to 68.80%. Remarkably, crystallographic analysis of these green energy-containing salts reveals substantial advantages in terms of thermodynamic stability and low sensitivity. Experimental investigations have demonstrated a positive relationship between the nitrogen content and the pyrothermal performance of the azotriazolone derivatives. Of particular significance is compound 5, a triaminoguanidine salt, which exhibits an exceptionally high nitrogen content of 68.80%. It displays a detonation pressure of 28.2 GPa and a detonation velocity of 7939.4 m s-1. Moreover, the derivatives of azotriazolone salts demonstrate the formation of nitrogen-rich compounds, characterized by insensitive properties, attributed to the hydrogen-bonded network structures resulting from anion-cation interactions. With the exception of compound 5, which exhibits a friction sensitivity of 252 N, the remaining derivatives show a similar value of approximately 360 N. This suggests that azotriazolone serves as a promising material possessing both stabilizing properties and better detonation performance, thereby providing a favorable platform for the synthesis of novel compounds with advantageous properties.
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