Evaluating the solvation properties of functionalized ionic liquids with varied cation/anion composition using the solvation parameter model

Twu, Pamela; Zhao, Qichao; Pitner, William R.; Acree, William E.; Baker, Gary A.; Anderson, Jared L.

doi:10.1016/j.chroma.2011.05.083

Cited by 38 publications

(26 citation statements)

References 21 publications

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“…This model, as described by Eq. (1), also allows separation scientists to establish quantitative structure-retention relationships to understand the role that IL structural features play on the selectivity in 1D-GC and GC × GC separations [30,31,35].…”

Section: Solvation Parameter Modelmentioning

confidence: 99%

Identifying important structural features of ionic liquid stationary phases for the selective separation of nonpolar analytes by comprehensive two-dimensional gas chromatography

Zhang

Ingram

Hantao

et al. 2015

Journal of Chromatography A

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Section: Solvation Parameter Modelmentioning

confidence: 99%

Identifying important structural features of ionic liquid stationary phases for the selective separation of nonpolar analytes by comprehensive two-dimensional gas chromatography

Zhang

Ingram

Hantao

et al. 2015

Journal of Chromatography A

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“…146 Kempter and Kirchner 147 provided an in-depth discussion about H-bonding in functionalized and non-functionalized ILs from both experimental and theoretical aspects. The Anderson group 148, 149 derived the solvation properties of functionalized ILs using a solvation parameter model and suggest that appending a hydroxyl moiety to the IL cation greatly increases its H-bond acidity with a small increase in H-bond basicity and no change in dipolarity. They also confirmed a slight increase in the H-bond basicity in the presence of ether functionality on the cations.…”

Section: Physicochemical Properties Of Ether- and Hydroxyl-functiomentioning

confidence: 99%

“…Breitbach and Armstrong 82 investigated a number of high thermal stability phosphonium ILs, including an ether-functionalized dicationic IL as stationary phase for gas–liquid chromatography (GLC), and indicated that different solvent properties of phosphonium ILs from alkylammonium ILs enable favorable separation selectivities. Twu et al 148 studied various ether/hydroxyl-functionalized and nonfunctionalized ILs as GC stationary phases, and reported that the retention behaviors of probe molecules in these IL-coated stationary phases serves as an excellent tool for examining the solvation characteristics and polarity of the ILs (see section 3.5. Polarity, hydrophilicity, and H-bonding capability ).…”

Section: Applications Of Ether- and Hydroxyl-functionalized Ilsmentioning

confidence: 99%

Ether- and alcohol-functionalized task-specific ionic liquids: attractive properties and applications

2012

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In recent years, the designer nature of ionic liquids (ILs) has driven their exploration and exploitation in countless fields among the physical and chemical sciences. A fair measure of the tremendous attention placed on these fluids has been attributed to their inherent designer nature. And yet, there are relatively few examples of reviews which emphasize this vital aspect in an exhaustive or meaningful way. In this critical review, we systematically survey the physicochemical properties of the collective library of ether- and alcohol-functionalized ILs, highlighting the impact of ionic structure on features such as viscosity, phase behavior/transitions, density, thermostability, electrochemical properties, and polarity (e.g., hydrophilicity, hydrogen bonding capability). In the latter portions of this review, we emphasize the attractive applications of these functionalized ILs across a range of disciplines, including their use as electrolytes or functional fluids for electrochemistry, extractions, biphasic systems, gas separations, carbon capture, carbohydrate dissolution (particularly, the (ligno)celluloses), polymer chemistry, antimicrobial and antielectrostatic agents, organic synthesis, biomolecular stabilization and activation, and nanoscience. Finally, this review discusses anion-functionalized ILs, including sulfur- and oxygen-functionalized analogs, as well as choline-based deep eutectic solvents (DESs), an emerging class of fluids which can be sensibly categorized as semi-molecular cousins to the IL. Finally, the toxicity and biodegradability of ether- and alcohol-functionalized ILs are discussed and cautiously evaluated in light of recent reports. By carefully summarizing literature examples on the properties and applications of oxy-functional designer ILs up till now, it is our intent that this review offer a barometer for gauging future advances in the field as well as a trigger to spur further contemplation of these seemingly inexhaustible and—relative to their potential—virtually untouched fluids. It is abundantly clear that these remarkable fluidic materials are here to stay, just as certain design rules are slowly beginning to emerge. However, in fairness, serendipity also still plays an undeniable role, highlighting the need for both expanded in silico studies and a beacon to attract bright, young researchers to the field.

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“…2 Besides ionic interactions, whether supramolecular interactions also govern the organization of imidazoliumbased ILs is still hotly debated with a vast number of important contributions. [24][25][26][27][28][29] Despite their importance, the number of significant contributions specifically discussing the supramolecular organization and interactions of TSILs is much scarcer [30][31][32][33][34][35][36][37][38][39][40][41][42][43][44][45] when compared to nonfunctionalized ILs. TSILs have become one of the most important strategies for furthering IL chemistry, 1 as noted for the large and increasing number of innovative applications described for these ionic compounds.…”

Section: Introductionmentioning

confidence: 99%

Solid, Solution and Gas Phase Interactions of an Imidazolium-Based Task-Specific Ionic Liquid Derived from Natural Kojic Acid

Neto¹,

Mota²,

Gatto³

et al. 2014

Journal of the Brazilian Chemical Society

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Um líquido iônico imidazólio de função específica derivado do ácido kójico natural teve suas interações supramoleculares investigadas no estado sólido, em solução e em fase gasosa. Diferentes técnicas como difração de raios X de monocristal, espectroscopia de ressonância magnética nuclear (NMR), espectrofotometria UV-Vis, medidas de condutividade, espalhamento de raios X em baixo ângulo (SAXS), espectrometria de massas (tandem) com ionização por electrospray (ESI-MS(/MS)) e cálculos teóricos permitiram uma investigação estrutural aprofundada desse líquido iônico de função específica e suas interações supramoleculares. An imidazolium-based task-specific ionic liquid derived from the natural kojic acid had its supramolecular interactions investigated in solid, solution and gas phase. The use of a set of techniques formed by single-crystal X-ray diffraction, nuclear magnetic resonance (NMR) spectroscopy, UV-Vis spectrophotometry, conductivity measurements, small angle X-ray scattering (SAXS), electrospray (tandem) mass spectrometry (ESI-MS(/MS)), and theoretical calculations allowed a deep investigation of the structural organization of the task-specific ionic liquid and its supramolecular interactions.Keywords: ionic liquids, imidazolium, task-specific ionic liquids, supramolecular interactions, organization, X-ray, SAXS, UV-Vis, NMR, ESI-MS IntroductionIonic liquids (ILs) and task-specific ionic liquids (TSILs), especially those based on the imidazolium cation, are part of a class of attractive compounds of widespread use in many scientific and technological areas.1-3 These organic salts have already been successfully used in the chemical industry for many years. 4 Their prominence is exemplified by many review articles recently published regarding several features of these unique chemical species. 5-21The possibility of tuning the physical and chemical properties of ILs and TSILs associated with their attractive physicochemical properties, such as very low vapor pressure, large electrochemical window, good thermal and chemical stabilities, have also opened a wealth of other applications for these ionic materials. Despite all progress already reached by ILs, fine details about their supramolecular organization, the importance of H-bonds and a deep understanding on the directionality of imidazolium-based derivatives are only now emerging. Each IL/TSIL has unique physicochemical properties and it has been estimated that ca. 10 6 combinations of known Neto et al. 2281 Vol. 25, No. 12, 2014 cations and anions may afford a new type of such ionic compounds. 22 The effort towards a better comprehension on the physicochemical properties of such materials is therefore very challenging; and each new structure demands specific efforts and a set of characterizations to depict its unique structural features and properties. Despite the diversity, some general trends have been established, and it is, for instance, known that the physicochemical properties of ILs/TSILs are intimately associated with their ionic structures, 23...

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Evaluating the solvation properties of functionalized ionic liquids with varied cation/anion composition using the solvation parameter model

Cited by 38 publications

References 21 publications

Identifying important structural features of ionic liquid stationary phases for the selective separation of nonpolar analytes by comprehensive two-dimensional gas chromatography

Identifying important structural features of ionic liquid stationary phases for the selective separation of nonpolar analytes by comprehensive two-dimensional gas chromatography

Ether- and alcohol-functionalized task-specific ionic liquids: attractive properties and applications

Solid, Solution and Gas Phase Interactions of an Imidazolium-Based Task-Specific Ionic Liquid Derived from Natural Kojic Acid

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