Introduction
Compared with traditional imidazolium ionic liquids (ILs), triazolium or tetrazolium ionic liquids showed the higher positive enthalpy of formation, the higher density, the lower sensitivity, the better thermal stability, and the higher oxygen balance due to the large number of N-N and C-N bonds [1]. And besides, triazolium and tetrazolium ionic liquids also showed advantages, such as very low vapor pressure, low hydrocarbon content, nitrogen as the major decomposition gas, and so on. Thus, triazolium or tetrazolium ionic liquids have been widely used as a high-energy material, explosives, and propellants in industry and military [2, 3]. At the same time, triazolium and tetrazolium ionic liquids were exploited as precursors of N-heterocyclic carbenes ligands for transition metal catalysts [4], also used as a solvent for dissolving cellulose [5]. Therefore, triazolium and tetrazolium ionic liquids were not only employed in the preparation of efficient catalysts and...
Reference
Zohari N, Abrishami F, Ebrahimikia M (2016) Investigation of the effect of various substituents on the density of tetrazolium nitrate salts as green energetic materials. Z Anorg Allg Chem 642:749–760
Singh RP, Verma RD, Meshri DT, Shreeve JM (2006) Energetic nitrogen-rich salts and ionic liquids. Angew Chem Int Ed 45:3584–3601
Zhang Q, Shreeve JM (2014) Energetic ionic liquids as explosives and propellant fuels: a new journey of ionic liquid chemistry. Chem Rev 114:10527–10574
Levin E, Ivry E, Diesendruck CE, Lemcoff NG (2015) Water in N-heterocyclic carbene-assisted catalysis. Chem Rev 115:4607–4692
Brehm M, Pulst M, Kressler J, Daniel S (2019) Triazolium-based ionic liquids: a novel class of cellulose solvents. J Phys Chem B 123:3994–4003
Schweinfurth D, Hettmanczyk L, Suntrup L, Sarkar B (2017) Metal complexes of click-derived triazoles and mesoionic carbenes: electron transfer, photochemistry, magnetic bistability, and catalysis. Z Anorg Allg Chem 643:554–584
Huynh HV (2018) Electronic properties of N-heterocyclic carbenes and their experimental determination. Chem Rev 118:9457–9492
Drake G, Hawkins T, Brand A, Hall L, Mckay M (2003) Energetic, low-melting salts of simple heterocycles. Propellants Explos Pyrot 28:174–180
Jin CM, Ye CF, Piekarski C, Twamley B, Shreeve JM (2003) Mono and bridged azolium picrates as energetic salts. Eur J Inorg Chem 2005:3760–3767
Kavun VY, Davidovich RL, Logvinova VB, Merkulov EB, Tkachev VV (2015) Synthesis, crystal structure, and NMR investigation of 4-amino-1,2,4-triazolium hexafluoridotitanate(IV). J Fluor Chem 178:68–72
Denault CC, Marx PC, Takimoto HH (1968) Energy of combustion and differential thermograms of organic azides. J Chem Eng Data 13:514–516
Singh D, Gardas RL (2016) Influence of cation size on the ionicity, fluidity, and physiochemical properties of 1,2,4-triazolium based ionic liquids. J Phys Chem B 120:4834–4842
Alpers T, Muesmann TWT, Temme O, Christoffers J (2018) Perfluorinated 1,2,3- and 1,2,4-triazolium ionic liquids. Eur J Org Chem 2018:4331–4337
Raiguel S, Thomas J, Binnemans K, Dehaen W (2018) Multi-gram scale synthesis of 1,2,3-triazolium ionic liquids and assay of their resistance towards bases. Eur J Org Chem 2018:4850–4856
Jaya P, Shrestha CW, Chang T (2013) Safe and easy route for the synthesis of 1,3-dimethyl-1,2,3-triazolium salt and investigation of its anticancer activities. Bioorg Med Chem Lett 23:5909–5911
Xue H, Gao Y, Twamley B, Shreeve JM (2005) New energetic salts based on nitrogen-containing heterocycles. Chem Mater 17:191–198
Haltsanelt S, Liebscher J (2008) A novel and versatile access to task-specific ionic liquids based on 1,2,3-triazolium salts. Synlett 2008:1058–1060
Xu XY, Li LF, Zhang ZY, Yan XY (2018) Nucleophilic substitution of 4-bromomethyltriazolium with different nucleophiles. Tetrahedron 74:6846–6853
Virant M, Košmrlj J (2019) Arylation of click triazoles with diaryliodonium salts. J Org Chem 84:14030–14044
Hutchinson SM, Ardón-Muñoz LG, Ratliff ML, Bolliger JL (2019) Catalytic preparation of 1-aryl-substituted 1,2,4-triazolium salts. ACS Omega 4:17923–17933
von Denffer M, Klapötke TM, Kramer G, Spieß G, Welch JM (2005) Improved synthesis and x-ray structure of 5-aminotetrazolium nitrate. Propellants Explos Pyrotech 30:191–195
Krukovskii IM, Molchanova MS, Evtushenko AV, Shlyapochnikov VA (1998) Qualitative estimation of the dependence of the number of energetic compounds on their oxygen coefficient. Russ Chem Bull 47:1266–1273
Tao GH, Guo Y, Parrish DA, Shreeve JM (2010) Energetic 1,5-diamino-4H-tetrazoliumnitro-substituted azolates. J Mater Chem 20:2999–3005
Xue H, Arritt SW, Twamley B, Shreeve JM (2004) Energetic salts from N-aminoazoles shreeve. Inorg Chem 43(25):7972–7977
Jones CB, Haiges R, Schroer T, Christe KO (2006) Oxygen-balanced energetic ionic liquid. Angew Chem Int Ed 45:4981–4984
Singh P, Kumar P, Kumari K, Sharma P, Mozumdar S, Chandra R (2011) A rapid and simple route for the synthesis of lead and palladium nanoparticles in tetrazolium based ionic liquid. Spectrochim Acta A 78:909–912
Aridoss G, Laali KK (2011) Highly efficient synthesis of 5-substituted 1H-tetrazoles catalyzed by Cu-Zn alloy nanopowder, conversion into 1,5- and 2,5-disubstituted tetrazoles, and synthesis and nmr studies of new tetrazolium ionic liquids. Eur J Org Chem 2011:6343–6355
Tona V, Maryasin B, de la Torre A, Sprachmann J, González L, Maulide N (2017) Direct regioselective synthesis of tetrazolium salts by activation of secondary amides under mild conditions. Org Lett 19:2662–2665
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Xiao, L. (2021). Trizxolium Ionic Liquids and Tetrazolium Ionic Liquids. In: Zhang, S. (eds) Encyclopedia of Ionic Liquids. Springer, Singapore. https://doi.org/10.1007/978-981-10-6739-6_123-1
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DOI: https://doi.org/10.1007/978-981-10-6739-6_123-1
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