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Novel 4, 5‐Dinitro‐ N , N′ ‐dialkylimidazolium Cations as Candidates for High‐energy Materials
Author(s) -
Kim Namtae,
Lee Byeongil,
Song Mingyu,
Jang Sewook,
Kwon Kuktae,
Kim Seunghee,
Kim Young Gyu
Publication year - 2021
Publication title -
bulletin of the korean chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.237
H-Index - 59
ISSN - 1229-5949
DOI - 10.1002/bkcs.12195
Subject(s) - tetrafluoroborate , ionic liquid , metathesis , imidazole , chemistry , nucleophile , reagent , trinitrotoluene , medicinal chemistry , ion , alkylation , explosive material , combinatorial chemistry , organic chemistry , catalysis , polymer , polymerization
In the synthesis of energetic ionic liquids (EILs), the quaternization of dinitroimidazoles remains a challenging task due to their reduced nucleophilicity. In this study, two new EILs precursors, 3‐ethyl‐1‐methyl‐4,5‐dinitro‐1 H ‐imidazol‐3‐ium tetrafluoroborate ( 1 ) and 1,3‐diethyl‐4,5‐dinitro‐1 H ‐imidazol‐3‐ium tetrafluoroborate ( 2 ) were obtained via the alkylation of 1‐methyl‐4,5‐dinitro‐1 H ‐imidazole and 4,5‐dinitro‐1 H ‐imidazole using Meerwein's reagents, respectively. The 4,5‐dinitroimidazolium cations are expected to be applied for new insensitive high‐energy materials (HEMs) via an anion metathesis reaction with energetic anions. Two new EILs, 3‐ethyl‐1‐methyl‐4,5‐dinitro‐1 H ‐imidazol‐3‐ium 2,4,5‐trinitroimidazol‐1‐ide ( 3 ) and 1,3‐diethyl‐4,5‐dinitro‐1 H ‐imidazol‐3‐ium 2,4,5‐trinitroimidazol‐1‐ide ( 4 ), were obtained as potential HEMs via the anion metathesis reaction with 2,4,5‐trinitroimidazol‐1‐ide. Although some improvements in the thermal properties are desired, compound 3 showed the promising properties as a new insensitive HEM because of its excellent insensitivity and more powerful explosive performance than those of 2,4,6‐trinitrotoluene (TNT).