The pursuit of heat-resistant energetic materials featuring
high
thermostability and energy has gained keen interest in recent years
owing to their use in coal mining and aerospace domains. In this study,
we synthesized 4-((4,6-diamino-1,3,5-triazin-2-yl) amino)-1H-1,2,3-triazole-5-carbonitrile (6) and its
perchlorate and nitrate energetic salts (6a and 6b) by incorporating amino bridging (−NH−) using
the Dimroth rearrangement (DR) from inexpensive starting materials
as a heat-resistant energetic materials. All of the compounds were
thoroughly characterized by infrared (IR), NMR, elemental analysis
(EA), high-resolution mass spectrometry (HRMS), and thermogravimetric
analysis-differential scanning calorimetry (TGA-DSC) studies. Compounds 6a and 6b showed good densities (1.81 and 1.80
g cm–3), detonation performance (VOD = 7505 and
8257 m s–1, DP = 23.47 and 24.41 GPa), insensitivity
to mechanical stimuli (IS = 40 J and FS = >360 N), and excellent
thermal
stability (T
d = 307 and 334 °C),
surpassing presently used heat-resistant explosive HNS (318 °C).
The molecular electrostatic potentials and noncovalent interactions
were pursued to understand possible interaction sites and structure-directing
interactions in these salts. Their facile synthetic approach, good
energetic performance, and outstanding thermal stability indicate
that they are the ideal combination for replacing current benchmark
heat-resistant explosive HNS. Additionally, this study highlights
the use of classical DR for making new energetic materials with fine-tuned
properties.