Analysis of 3,6-Dihydrazinyl-1,2,4,5-Tetrazine Macrocycles and Polymers – Towards Novel Energetic Macromolecules

Adva Cohen, Chemistry, Tel Aviv University, Tel Aviv, Israel
Qi-Long Yan, Chemistry, Tel Aviv University, Tel Aviv, Israel
Avital Shlomovich, Chemistry, Tel Aviv University, Tel Aviv, Israel
Alexander Aizikovich, Chemistry, Tel Aviv University, Tel Aviv, Israel
Natan Petrutik, Chemistry, Tel Aviv University, Tel Aviv, Israel
Noa Klein, Chemistry, Tel Aviv University, Tel Aviv, Israel
Michael Gozin, Chemistry, Tel Aviv University, Tel Aviv, Israel

A new family of nitrogen-rich energetic macromolecules was synthesized by reacting 3,6-dihydrazinyl-1,2,4,5-tetrazine (DHTZ) with a series of diisocyanates. It was shown that polymeric or macrocyclic structures could be formed under certain reaction conditions (dilution, solvents, temperature etc.). For optimization of reaction conditions towards specific macrocyclic products, oligomerization processes were monitored by ESI MS. Our new energetic macrocycles were designed to possess a significant metal-binding affinity and to function as potential combustion catalysts. It was shown that macrocycles had a consistency of powders, while the polymers had a tendency to form films. We also found that our new macrocycles could function as gelators of organic solvents, such as DMF and DMSO. Resulted macrocycles and polymers were comprehensively characterized by IR, NMR, high resolution MS and SEM, while their thermal stability was studied by DSC.