The more energy is stored in a molecule, the less stable and more sensitive it usually is. This makes the synthesis of energetic materials with an ideal combination of energetic properties (high detonation velocity and pressure), stability (decomposition temperature > 200 °C), and sensitivity (high impact and friction sensitivity) difficult.

Jean’ne M. Shreeve, University of Idaho, Moscow, USA, and colleagues have synthesized the fused-ring conjugated energetic molecule 4-amino-3,7-dinitro-[1,2,4]triazolo[5,1-c] [1,2,4]triazine (TTX, pictured). The synthesis involves a two-step procedure starting from 3-Amino-5-nitro-l,2,4-triazole. (ANTA). TTX has energetic properties comparable to those of 1,3,5-trinitro-1,3,5-triazacyclohexane (RDX), another established energetic molecule, but with a higher thermal stability and lower sensitivity towards impact and friction.

Characterization by NMR and infrared (IR) spectroscopy, mass spectrometry (MS), and elemental analysis showed that strong hydrogen bonding and nitro-π interactions, along with the planar-conjugated structure of TTX, contribute significantly to its thermal stability and insensitivity. Its excellent properties and easy synthesis make it a suitable molecule for energetic applications in which both high performance and safety is important.

• A Highly Stable and Insensitive Fused Triazolo-Triazine Explosive (TTX),
  Dheeraj Kumar, Gregory H. Imler, Damon A. Parrish, Jean’ne M. Shreeve,
  Chem. Eur. J. 2016.
  DOI: 10.1002/chem.201604919