Intramolecular Hydrogen Bonds Assisted Construction of Planar Tricyclic Structures for Insensitive and Highly Thermostable Energetic Materials

• Published in: International journal of molecular sciences Vol. 25; no. 7; p. 3910
• Main Authors: Liu, Yubing, Li, Jie, Cai, Jinxiong, Zhang, Xun, Hu, Lu, Pang, Siping, He, Chunlin
• Format: Journal Article
• Language: English
• Published: Switzerland MDPI AG 01.04.2024
• Subjects: Amines; Bandages; Computer software industry; Crystals; Decomposition; energetic compounds; Hydrogen; Hydrogen Bonding; Hydrogen bonds; intramolecular hydrogen; planar structure; Potassium; Spectrum analysis; stability; tricyclic frameworks; United States; energetic compounds; intramolecular hydrogen; stability; tricyclic frameworks; planar structure
• ISSN: 1422-0067; 1661-6596; 1422-0067
• DOI: 10.3390/ijms25073910

Safety is fundamental for the practical development and application of energetic materials. Three tricyclic energetic compounds, namely, 1,3-di(1H-tetrazol-5-yl)-1H-1,2,4-triazol-5-amine ( ), 5'-nitro-3-(1H-tetrazol-5-yl)-2'H-[1,3'-bi(1,2,4-triazol)]-5-amine ( ), and 1-(3,4-dinitro-1H-pyrazol-5-yl)-3-(1H-tetrazol-5-yl)-1H-1,2,4-triazol-5-amine ( ), were effectively synthesized through a simple two-step synthetic route. The introduction of intramolecular hydrogen bonds resulted in excellent molecular planarity for the three new compounds. Additionally, they exhibit regular crystal packing, leading to numerous intermolecular hydrogen bonds and π-π interactions. Benefiting from planar tricyclic structural features, , , and are insensitive ( > 60 J, = 360 N) when exposed to external stimuli. Furthermore, ( = 361.1 °C) and ( = 317.0 °C) exhibit high decomposition temperatures and satisfying detonation performance. The intermolecular hydrogen bonding that produced this planar tricyclic molecular structure serves as a model for the creation of innovative multiple heterocycle energetic materials with excellent stability.