1-Butyl-3-methylimidazolium 3,5-dinitro-1,2,4-triazolate: a novel ionic liquid containing a rigid, planar energetic anion

Katritzky, Alan R.; Singh, Shailendra P.; Kirichenko, Kostyantyn; Holbrey, John D.; Śmiglak, Marcin; Reichert, W. Matthew; Rogers, Robin D.

doi:10.1039/b414683b

Cited by 110 publications

(79 citation statements)

References 16 publications

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“…Some alkene-substituted anions have also been introduced for synthesis of polymeric materials [84,85] . Very recently, there are also few anions based on triazole backbone reported [86][87][88] . They have higher melting points and viscosities, but have potential applications in energetic materials.…”

Section: Functionalization Of Ionic Liquidsmentioning

confidence: 99%

Applications of functionalized ionic liquids

Zhao

Fei

et al. 2006

SCI CHINA SER B

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Section: Functionalization Of Ionic Liquidsmentioning

confidence: 99%

Applications of functionalized ionic liquids

Zhao

Fei

et al. 2006

SCI CHINA SER B

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“…Among others, triazolium-based energetic materials have found use as high explosives, [20] gas generators [21] and ionic liquids. [22] This last material may possibly find application in melt-cast explosives.…”

Section: Introductionmentioning

confidence: 99%

1,2,4‐Triazolium‐Cation‐Based Energetic Salts

Darwich

Klapötke

Sabaté

2008

Chemistry A European J

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3,4,5-Triamino-1,2,4-triazole (guanazine, 1) can be readily methylated with methyl iodide yielding methylguanazinium iodide (2). Salts containing the novel methylguanazinium cation with energetic anions were synthesised by metathesis reactions with silver azide (3), silver nitrate (4), silver perchlorate (5), sodium 5,5'-azotetrazolate (6), silver 5-nitrotetrazolate (7) and silver dinitramide (8), yielding a new family of heterocycle-based salts, which were fully characterised by analytical (mass spectrometry and elemental analysis) and spectroscopic methods (IR, Raman and NMR). In addition, the molecular structures of all compounds were confirmed by X-ray analysis, revealing extensive hydrogen-bonding in the solid state and densities between 1.399 (3) and 1.669 g cm(-3) (5). The hydrogen-bonded ring motifs are discussed in the formalism of graph-set analysis for hydrogen-bond patterns and compared to each other. Preliminary sensitivity testing of the crystalline compounds indicate surprisingly low sensitivities to both friction and impact, the highest friction and shock sensitivity being found for the perchlorate (5, 220 N) and the dinitramide (8, 20 J) salts, respectively. In addition, DSC analysis was used to assess the thermal stabilities of the compounds: 3-6 melt above 200 degrees C with concomitant decomposition, whereas 7 and 8 have clearly defined melting points at 162 and 129 degrees C, respectively, and with decomposition occurring about 30 degrees C above the melting point. Lastly all compounds have positive calculated heats of formation between 336 (4) and 4070 kJ kg(-1) (6) and calculated detonation velocities in the range between 8330 (7) and 8922 m s(-1) (6) making them of interest as new highly energetic materials with low sensitivity.

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“…It is interesting that triazole and tetrazole act as acids to afford suitable anions for low-temperature ionic liquids. Salts obtained in this experiment showed very low viscosity, 54 …”

Section: Halogen-free Ionic Liquidsmentioning

confidence: 99%

Functional Design of Ionic Liquids

Ohno

2006

Bulletin of the Chemical Society of Japan

246

158

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Ionic liquids, molten salts at temperatures lower than 100 C, preferably below room temperature, are unique liquids having very different characteristics from ordinary molecular liquids. Since these ionic liquids are prepared by coupling relatively large organic ions, there are many chances to create novel functionalities by changing structure of component ions. To develop such novel and functional ionic liquids, we first developed a facile preparation method, i.e., neutralization of tertiary amines with organic acids. By this convenient method, we prepared hundreds of salts having low melting points. We, then, tried to prepare ionic salts containing small ions such as lithium cation, proton, or chloride anion. Because small ions received stronger electrostatic force due to higher surface charge density, which results in the formation of salts with higher melting points, case must be taken. Ionic liquids containing halogen-free salts are another interesting subject to challenge from the viewpoint of environmentally friendly materials. Heteroaromatic rings such as azolates gave excellent ionic liquids having very low viscosity by coupling with suitable cations. Amino acids have also been used as anions to prepare salts with low melting points or amorphous glasses. They are helpful to analyze the relationship between ion structure and characteristics of the salts. Zwitterions, in which both cation and anion were tethered with a covalent bond, were prepared to function as ionic liquids. These ions should not migrate under a potential gradient and should be an excellent ion conductive matrix for added ions. Tethering of ions caused the T m to be high, and the zwitterions with melting points around room temperature have not been synthesized yet. However, lots of solid zwitterions became liquids by adding suitable solid salts or acid such as lithium bis(trifluoromethanesulfonyl)imide. In this mixture, lithium cations had a transport number higher than 0.5, meaning that the lithium cations are the major mobile ions in the mixture. Some of the functionality is achieved by dimension control, such as polymerization of ions, and so on. Other functional modifications and design of ionic liquids are also mentioned.

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1-Butyl-3-methylimidazolium 3,5-dinitro-1,2,4-triazolate: a novel ionic liquid containing a rigid, planar energetic anion

Cited by 110 publications

References 16 publications

Applications of functionalized ionic liquids

Applications of functionalized ionic liquids

1,2,4‐Triazolium‐Cation‐Based Energetic Salts

Functional Design of Ionic Liquids

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