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Synthesis and properties of alkoxy- and alkenyl-substituted peralkylated imidazolium ionic liquids

(2013) CHEMPHYSCHEM. 14(15). p.3503-3516
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Abstract
Novel peralkylated imidazolium ionic liquids bearing alkoxy and/or alkenyl side chains have been synthesized and studied. Different synthetic routes towards the imidazoles and the ionic liquids comprising bromide, iodide, methanesulfonate, bis(trifluoromethylsulfonyl) imide ([NTf2](-)), and dicyanamide {[N(CN)(2)](-)} as the anion were evaluated, and this led to a library of analogues, for which the melting points, viscosities, and electrochemical windows were determined. Incorporation of alkenyl moieties hindered solidification, except for cations with high symmetry. The alkoxy-derivatized ionic liquids are often crystalline; however, room-temperature ionic liquids (RTILs) were obtained with the weakly coordinating anions [N(CN)(2)](-) and [N(CN)(2)](-). For the viscosities of the peralkylated RTILs, an opposite trend was found, that is, the alkoxy derivatives are less viscous than their alkenyl-substituted analogues. Of the crystalline compounds, X-ray diffraction data were recorded and related to their molecular properties. Upon alkoxy substitution, the electrochemical cathodic limit potential was found to be more positive, whereas the complete electrochemical window of the alkenyl-substituted imidazolium salts was shifted to somewhat more positive potentials.
Keywords
molecular properties, ionic liquids, CATIONS, CHAINS, SALTS, X-ray diffraction, PHYSICAL-PROPERTIES, CRYSTAL-STRUCTURES, STRONG BASES, X-RAY, LIGANDS, green chemistry, cyclic voltammetry

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MLA
Maton, Cédric, Neil R Brooks, Luc Van Meervelt, et al. “Synthesis and Properties of Alkoxy- and Alkenyl-substituted Peralkylated Imidazolium Ionic Liquids.” CHEMPHYSCHEM 14.15 (2013): 3503–3516. Print.
APA
Maton, C., Brooks, N. R., Van Meervelt, L., Binnemans, K., Schaltin, S., Fransaer, J., & Stevens, C. (2013). Synthesis and properties of alkoxy- and alkenyl-substituted peralkylated imidazolium ionic liquids. CHEMPHYSCHEM, 14(15), 3503–3516.
Chicago author-date
Maton, Cédric, Neil R Brooks, Luc Van Meervelt, Koen Binnemans, Stijn Schaltin, Jan Fransaer, and Christian Stevens. 2013. “Synthesis and Properties of Alkoxy- and Alkenyl-substituted Peralkylated Imidazolium Ionic Liquids.” Chemphyschem 14 (15): 3503–3516.
Chicago author-date (all authors)
Maton, Cédric, Neil R Brooks, Luc Van Meervelt, Koen Binnemans, Stijn Schaltin, Jan Fransaer, and Christian Stevens. 2013. “Synthesis and Properties of Alkoxy- and Alkenyl-substituted Peralkylated Imidazolium Ionic Liquids.” Chemphyschem 14 (15): 3503–3516.
Vancouver
1.
Maton C, Brooks NR, Van Meervelt L, Binnemans K, Schaltin S, Fransaer J, et al. Synthesis and properties of alkoxy- and alkenyl-substituted peralkylated imidazolium ionic liquids. CHEMPHYSCHEM. 2013;14(15):3503–16.
IEEE
[1]
C. Maton et al., “Synthesis and properties of alkoxy- and alkenyl-substituted peralkylated imidazolium ionic liquids,” CHEMPHYSCHEM, vol. 14, no. 15, pp. 3503–3516, 2013.
@article{4428711,
  abstract     = {Novel peralkylated imidazolium ionic liquids bearing alkoxy and/or alkenyl side chains have been synthesized and studied. Different synthetic routes towards the imidazoles and the ionic liquids comprising bromide, iodide, methanesulfonate, bis(trifluoromethylsulfonyl) imide ([NTf2](-)), and dicyanamide {[N(CN)(2)](-)} as the anion were evaluated, and this led to a library of analogues, for which the melting points, viscosities, and electrochemical windows were determined. Incorporation of alkenyl moieties hindered solidification, except for cations with high symmetry. The alkoxy-derivatized ionic liquids are often crystalline; however, room-temperature ionic liquids (RTILs) were obtained with the weakly coordinating anions [N(CN)(2)](-) and [N(CN)(2)](-). For the viscosities of the peralkylated RTILs, an opposite trend was found, that is, the alkoxy derivatives are less viscous than their alkenyl-substituted analogues. Of the crystalline compounds, X-ray diffraction data were recorded and related to their molecular properties. Upon alkoxy substitution, the electrochemical cathodic limit potential was found to be more positive, whereas the complete electrochemical window of the alkenyl-substituted imidazolium salts was shifted to somewhat more positive potentials.},
  author       = {Maton, Cédric and Brooks, Neil R and Van Meervelt, Luc and Binnemans, Koen and Schaltin, Stijn and Fransaer, Jan and Stevens, Christian},
  issn         = {1439-4235},
  journal      = {CHEMPHYSCHEM},
  keywords     = {molecular properties,ionic liquids,CATIONS,CHAINS,SALTS,X-ray diffraction,PHYSICAL-PROPERTIES,CRYSTAL-STRUCTURES,STRONG BASES,X-RAY,LIGANDS,green chemistry,cyclic voltammetry},
  language     = {eng},
  number       = {15},
  pages        = {3503--3516},
  title        = {Synthesis and properties of alkoxy- and alkenyl-substituted peralkylated imidazolium ionic liquids},
  url          = {http://dx.doi.org/10.1002/cphc.201300611},
  volume       = {14},
  year         = {2013},
}

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