Effect of the alkyl chain length in 1-alkyl-3-methylimidazolium ionic liquids on inter-molecular interactions and rotational dynamics

Garaga, Mounesha N.; Nayeri, Moheb; Martinelli, Anna

doi:10.1016/j.molliq.2015.06.055

Cited by 80 publications

(53 citation statements)

References 59 publications

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“…The molecules of the IL-surfactant mixture adsorbed at the interface, even at low surfactant concentration, cause the reduction of the surface tension of water. Possible interactions with the surfactant adsorption are hydrophobic effect, electrostatic interaction, van der Waals interaction, hydrogen bonding, 12,14,38,39 etc.…”

Section: Surface Tension Measurementmentioning

confidence: 99%

Surface adsorption and thermodynamic properties of mixed system of ionic liquid surfactants with cetyltrimethyl ammonium bromide

Wang

2017

RSC Adv.

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Section: Surface Tension Measurementmentioning

confidence: 99%

Surface adsorption and thermodynamic properties of mixed system of ionic liquid surfactants with cetyltrimethyl ammonium bromide

Wang

2017

RSC Adv.

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“…However, recent works have shown that ionic size argumentations alone are not enough to describe the transport properties in ionic liquids through the Stokes‐Einstein relation, and that preferential diffusion paths or local micro‐viscosities may also play a role 1. Hence, ions with different sizes can diffuse at the same rate 37 and ions with similar sizes can experience different local micro‐viscosities 38. Therefore, conclusions about the association degree in ionic liquids should not be drawn from diffusion data only, but rather be supported by an investigation of inter‐molecular interactions and conductive properties ( vide infra ).…”

Section: Resultsmentioning

confidence: 99%

Transport Properties, Local Coordination, and Thermal Stability of the Water/Diethylmethylammonium Methanesulfonate Binary System

2015

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Ammonium based protic ionic liquids are highlighted for their great potential to sustain proton transport in proton exchange membrane (PEM) fuel cells. Yet, there remain questions concerning the effect of water produced by the fuel cell at the cathode side on the performance of the ionic liquid. In this contribution we report the effect of water on the transport properties and the local coordination in the binary system of the protic ionic liquid diethylmethylammonium methanesulfonate ([DEMA][OMs]) and water, employing 1H NMR, Raman, and infrared spectroscopy. We observe that the self‐diffusion of cations and anions increases with the water content and that cations and anions diffuse at the same rate at all concentrations investigated. 1H NMR and vibrational spectroscopy, on the other hand, indicate that added water interacts primarily with the anion and slightly affects the ionicity of the ionic liquid. In addition, by investigating the thermal stability of the binary system we find that although [DEMA][OMs] displays a continuous loss of water upon increasing temperature a fraction of water molecules can be retained even above 120 °C, and that the complete loss of water is immediately followed by decomposition, which is observed to occur at about 185 °C.

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“…The hydrogen bonds between the like ions led to the formation of interesting chain-like, ringlike, or distinct dimeric (i. e. two ion pairs) supermolecular clusters. [7][8][9][10][11][12][13][14] Studying ILs with functionalized side chains is another highly active area of research that aims at understanding the structure-property relationships. In this arrangement, the Cl À anions function as a bridge between the cations by establishing bifurcated hydrogen bonds with the OH group of one cation and the C(2)-H of another cation.…”

mentioning

confidence: 99%

“…[7][8][9][10][11][12][13][14] Studying ILs with functionalized side chains is another highly active area of research that aims at understanding the structure-property relationships. There are long-range coulombic forces due to the charges of the ions, dispersion forces between aliphatic chains, as well as hydrogen bonding.…”

mentioning

confidence: 99%

“…For example, varying the alkyl chain length in 1,3-dialkylimidazolium ILs or changing the anion was performed in many studies. [7][8][9][10][11][12][13][14] Studying ILs with functionalized side chains is another highly active area of research that aims at understanding the structure-property relationships. In particular, substituting alkyl chains by hydroxyl-functionalized moieties is currently very popular as this adds a further group that can potentially form hydrogen bonds.…”

mentioning

confidence: 99%

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Cluster Formation through Hydrogen Bond Bridges across Chloride Anions in a Hydroxyl‐Functionalized Ionic Liquid

et al. 2019

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Several recent studies of hydroxyl-functionalized ionic liquids (ILs) have shown that cation-cation interactions can be dominating these materials at the molecular level when the anion involved is weakly interacting. The hydrogen bonds between the like ions led to the formation of interesting chain-like, ringlike, or distinct dimeric (i. e. two ion pairs) supermolecular clusters. In the present work, vibrational spectroscopy (ATR-IR and Raman) and density functional theory (DFT) calculations of the hydroxyl-functionalized imidazolium ionic liquid C 2 OHmimCl indicate that anion-cation hydrogen bonding interactions are dominating, leading to the formation of distinct dimeric ion pair clusters. In this arrangement, the Cl À anions function as a bridge between the cations by establishing bifurcated hydrogen bonds with the OH group of one cation and the C(2)-H of another cation. Cation-cation interactions, on the other hand, do not play a significant role in the observed clusters.Ionic liquids (ILs) are fascinating materials and have received considerable attention in academia as well as industry over the past 20 years. The tunability of their properties via combining suitable cations and anions makes them attractive for applications in a variety of fields including organic synthesis, catalysis, electrochemistry, and separation. [1][2][3][4] These designable proper-ties (e. g. viscosity, electrical conductivity, and non-volatility) are determined by the molecular interactions between the ions. Therefore, unravelling the structure-property relationships and finding universal correlations that can be utilized for a rational design, i. e. without the need for extensive trial-and-error testing, is an important goal. [5,6] In fact, a full understanding of how the chemical structure of the ions and the interionic forces effect the macroscopic properties of an IL will be a game changer.The molecular interactions inside ILs are rather complicated compared to other classes of materials. There are long-range coulombic forces due to the charges of the ions, dispersion forces between aliphatic chains, as well as hydrogen bonding. The interplay of these interactions yields a local structure and produces micro/mesoscopic local domains. Studying how these phenomena affect the macroscopic properties has been and still is a hot topic in chemistry and chemical engineering. A common approach is to investigate series of ILs with a systematically changing structure in one ion while keeping the other ion constant. For example, varying the alkyl chain length in 1,3-dialkylimidazolium ILs or changing the anion was performed in many studies. [7][8][9][10][11][12][13][14] Studying ILs with functionalized side chains is another highly active area of research that aims at understanding the structure-property relationships. In particular, substituting alkyl chains by hydroxyl-functionalized moieties is currently very popular as this adds a further group that can potentially form hydrogen bonds. These hydroxyl-functionalized ILs were developed fo...

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Effect of the alkyl chain length in 1-alkyl-3-methylimidazolium ionic liquids on inter-molecular interactions and rotational dynamics

Cited by 80 publications

References 59 publications

Surface adsorption and thermodynamic properties of mixed system of ionic liquid surfactants with cetyltrimethyl ammonium bromide

Surface adsorption and thermodynamic properties of mixed system of ionic liquid surfactants with cetyltrimethyl ammonium bromide

Transport Properties, Local Coordination, and Thermal Stability of the Water/Diethylmethylammonium Methanesulfonate Binary System

Cluster Formation through Hydrogen Bond Bridges across Chloride Anions in a Hydroxyl‐Functionalized Ionic Liquid

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