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Synthesis of gem ‐Dinitromethylated and Fluorodinitromethylated Derivatives of 5,5′‐Dinitro‐bis‐1,2,4‐triazole as Promising High‐Energy‐Density Materials
Author(s) -
Huang Shi,
Tian Junjun,
Qi Xiujuan,
Wang Kangcai,
Zhang Qinghua
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201702451
Subject(s) - monoclinic crystal system , differential scanning calorimetry , ionic bonding , 1,2,4 triazole , crystallography , chemistry , proton nmr , crystal structure , single crystal , materials science , medicinal chemistry , stereochemistry , organic chemistry , ion , physics , thermodynamics
gem ‐Dinitromethylated and fluorodinitromethylated 5,5′‐dinitro‐3,3′‐bis‐1,2,4‐triazole (DNBT) ( 2 and 3 ) along with seven ionic derivatives 4 – 9 , were synthesized and characterized by NMR and IR spectroscopies, elemental analysis, single‐crystal X‐ray diffraction (XRD), and differential scanning calorimetry (DSC). XRD revealed that compounds 2 and 3 crystallized in the monoclinic P 2 1 / n space group and compound 5 crystallized in the monoclinic P 2 1 / c space group. The physicochemical properties of the as‐synthesized compounds 2 – 9 were investigated and the results indicated that compounds 3 , 6 , and 7 exhibited a good balance between high energy and low sensitivity, demonstrating their potential as new high‐energy‐density materials (HEDMs). The proposed synthetic strategy for introducing gem ‐dinitromethyl and fluorodinitromethyl groups into the DNBT framework to prepare materials with high energy and low sensitivity suitable for HEDMs looks promising.