Solvatochromic probes behaviour within ternary room temperature 1-butyl-3-methyl imidazolium tetrafluoroborate + methanol + water solutions

Journal of Molecular Liquids - Tập 344 - Trang 117767 - 2021
Md Rabiul Islam1, Maroof Ali1
1Department of Chemistry, Aligarh Muslim University, Aligarh, U.P., 202002, India

Tài liệu tham khảo

Rafiee, 2017, The study of solute-solvent interactions in the ternary Amino acid (Glycine or L-serine) + ionic liquid (1-butyl-3-methylimidazolium tetra fluoroborate [Bmim][BF4]) + H2O system at different temperatures and ambient pressure: Volumetric Study, J Mol. Liq., 230, 6, 10.1016/j.molliq.2016.12.116 Chhotaray, 2014, Physicochemical properties of low viscous lactam based ionic liquids, J. Chem. Thermodyn., 74, 255, 10.1016/j.jct.2014.02.009 Rodríguez, 2010, Liquid mixtures of ionic liquids and polymers as solvent systems, Fluid Phase Equilib., 294, 7, 10.1016/j.fluid.2009.12.036 Singh, 2015, Effect of protic ionic liquid on the volumetric properties and taste behaviour of sucrose, Food Chem., 169, 478, 10.1016/j.foodchem.2014.08.023 Shao, 2013, On the influence of hydrated imidazolium-based ionic liquid on protein structure stability: A molecular dynamics simulation study, J. Chem. Phys., 139, 115102, 10.1063/1.4821588 Rafiee, 2017, J. Mol. Liq., 248, 406, 10.1016/j.molliq.2017.10.084 Hayes, 2013, The Nature of Hydrogen Bonding in Protic Ionic Liquids, Angew. Chem., 125, 4721, 10.1002/ange.201209273 Freemantle, 2000, EYES ON IONIC LIQUIDS NATO workshop examines the industrial potential of green chemistry using room-temperature 'designer solvents', Chem. Eng. News, 78, 37, 10.1021/cen-v078n020.p037 Marcinkowska, 2019, Application of ionic liquids in microextraction techniques: Current trends and future perspectives, Trends Anal. Chem., 119, 115614, 10.1016/j.trac.2019.07.025 Aghaie, 2019, Assessment of carbon dioxide solubility in ionic liquid/toluene/water systems by extended PR and PC-SAFT EOSs: Carbon capture implication, J. Mol. Liq., 275, 323, 10.1016/j.molliq.2018.11.038 Yang, 2018, Effect of ionic liquid based imidazoliumas an additive on the formation of polymer/salt aqueous biphasic systems, J. Mol. Liq., 256, 1, 10.1016/j.molliq.2018.01.182 Camelo, 2021, Pre-purification of genipin from genipap using aqueous-two-phase systems composed of protic ionic liquids + polymers + water at 298 K and atmospheric pressure, Sep. Purif. Technol., 256, 117843, 10.1016/j.seppur.2020.117843 Livi, 2010, A comparative study on different ionic liquids used as surfactants: Effect on thermal and mechanical properties of high-density polyethylene nanocomposites, J. Colloid Interface Sci., 349, 424, 10.1016/j.jcis.2009.09.036 Vázquez-Fernández, 2021, Protic Ionic liquids/poly(vinylidene fluoride) composite membranes for fuel cell application, J. Energy Chem., 53, 197, 10.1016/j.jechem.2020.04.022 Durski, 2020, Separation of thiophene from octane/hexadecane with ionic liquids in ternary liquid-liquid phase equilibrium, Fluid Phase Equilib., 509, 112467, 10.1016/j.fluid.2020.112467 Mohammadi, 2019, Ionic-Liquid-Modified Carbon Quantum Dots as a Support for the Immobilization of Tungstate Ions (WO42–): Heterogeneous Nanocatalysts for the Oxidation of Alcohols in Water, ACS Sustainable Chem. Eng., 7, 5283, 10.1021/acssuschemeng.8b06279 Wang, 2021, Ionic liquid reducing energy loss and stabilizing CsPbI2Br solar cells, Nano Energy, 81, 105631, 10.1016/j.nanoen.2020.105631 Shet, 2020, Engineering Quantum Dots with Ionic Liquid: A Multifunctional White Light Emitting Hydrogel for Enzyme Packaging, Adv. Optical Mater., 8, 1902022, 10.1002/adom.201902022 Tripathi, 2021, Ionic liquid–based solid electrolytes (ionogels) for application in rechargeable lithium battery, Mater. Today Energy, 20, 100643, 10.1016/j.mtener.2021.100643 Adawiyah, 2016, Ionic liquids as a potential tool for drug delivery systems, Chem. Commun., 7, 1881, 10.1039/C6MD00358C Roses, 1995, Solute-solvent and solvent-solvent interactions in binary solvent mixtures. Part 1. A comparison of several preferential solvation models for describing ET (30) polarity of dipolar hydrogen bond acceptor-cosolvent mixtures, J. Chem. Soc., Perkin Trans, 2, 1607, 10.1039/P29950001607 Islam, 2019, Solvatochromic Absorbance and Fluorescence Probe Behavior within Ionic Liquid + γ-Butyrolactone Mixture, J. Chem. Eng. Data, 64, 4169, 10.1021/acs.jced.9b00576 Fletcher, 2003, Solvatochromic Probe Behavior within Ternary Room-Temperature Ionic Liquid 1-Butyl-3-methylimidazolium Hexafluorophosphate + Ethanol +Water Solutions, J. Phys. Chem. B, 107, 13532, 10.1021/jp0276754 Wu, 2009, Insight into the Intermolecular Interactions in [Bmim]BF4/[Amim]Cl-Ethanol-Water Mixtures by Near-Infrared Spectroscopy, J. Phys. Chem. B, 113, 12332, 10.1021/jp905252j Rilo, 2010, Densities and derived thermodynamic properties of ternary mixtures 1-butyl-3-methyl imidazolium tetrafluoroborate + ethanol + water at seven pressures and two temperatures, Fluid Phase Equilib., 296, 53, 10.1016/j.fluid.2010.03.039 Deenadayalu, 2006, Liquid-Liquid Equilibria for Ternary Mixtures (an Ionic Liquid + Benzene + Heptane or Hexadecane) at Temp (298.2 K) and Atmospheric Pressure, J. Chem. Eng. Data, 51, 988, 10.1021/je050494l Rodríguez, 2001, Physical Properties and Liquid-Liquid Equilibrium of the Ternary Mixture (Dimethyl Carbonate + Methanol + Hexane) at 298.15 K, J. Chem. Eng. Data, 46, 184, 10.1021/je000180s Waris, 1988, Py and BPe solvent polarity scales: effect of temperature on pyrene and benzo[ghi]perylene fluorescence spectra, Analyst, 113, 1465, 10.1039/an9881301465 Dong, 1984, The Py scale of solvent polarities, Can. J. Chem., 62, 2560, 10.1139/v84-437 Karpovich, 1995, Relating the Polarity Dependent Fluorescence Response of Pyrene to Vibronic Coupling. Achieving a Fundamental Understanding of the Py Polarity Scale, J. Phys. Chem., 99, 3951, 10.1021/j100012a014 Sarkar, 2009, Multiprobe Spectroscopic Investigation of Molecular-level Behavior within Aqueous 1-Butyl-3-methylimidazolium Tetrafluoroborate, J. Phys. Chem. B, 113, 3088, 10.1021/jp8098297 Silva, 2002, Preferential Solvation of a Hydrophobic Probe in Binary Mixtures Comprised of a Nonprotic and a Hydroxylic Solvent: A View of Solute-Solvent and Solvent-Solvent Interactions, J. Phys. Chem. A, 106, 8820, 10.1021/jp0145964 Marcus, 1994, Use of chemical probes for the characterization of solvent mixtures. Part 1. Completely non-aqueous mixtures, J. Chem. Soc., Perkin Trans., 25, 1015, 10.1039/p29940001015 Chatterjee, 1991, Preferential solvation in mixed binary solvents by ultraviolet–visible spectroscopy: N-ethyl-4-cyanopyridinium iodide in alcohol–acetone mixtures, J. Chem. Soc., Faraday Trans., 87, 587, 10.1039/FT9918700587 Bosch, 1992, Relationship between ET polarity and composition in binary solvent mixtures, J. Chem. Soc., Faraday Trans., 88, 3541, 10.1039/FT9928803541 Phillips, 1993, Spectroscopic measurement of local compositions in binary liquid solvents and comparison to the NRTL equation, Ind. Eng. Chem. Res., 32, 943, 10.1021/ie00017a024 Acree, 1994, Spectrochemical Investigations of Preferential Solvation. 2. Compatibility of Thermodynamic Models versus Spectrofluorometric Probe Methods for Tautomeric Solutes Dissolved in Binary Mixtures, J. Phys. Chem., 98, 2537, 10.1021/j100061a007 Kalyanasundaram, 1977, Solvent-dependent fluorescence of pyrene-3-carboxaldehyde and its applications in the estimation of polarity at micelle-water interfaces, J. Phys. Chem., 81, 2176, 10.1021/j100538a008 Bredereck, 1960 Pandey, 2012, Fluorescent Probe Studies of Polarity and Solvation within Room Temperature Ionic Liquids: A Review, J. Fluoresc., 22, 1313, 10.1007/s10895-012-1073-x Reichardt, 1994, Solvatochromic Dyes as Solvent Polarity Indicators, Chem. Rev., 94, 2319, 10.1021/cr00032a005 Reichardt, 1988 Harifi-Mood, 2006, Solvatochromic Parameters for Binary Mixtures of 1-(1-Butyl)-3-methylimidazolium Tetrafluoroborate with Some Protic Molecular Solvents, J. Phys. Chem. B, 110, 7073, 10.1021/jp0602373 Kamlet, 1977, The solvatochromic comparison method. 6. The.pi.* scale of solvent polarities, J. Am. Chem. Soc., 99, 6027, 10.1021/ja00460a031 Taft, 1976, The solvatochromic comparison method. 2. The.alpha.-scale of solvent hydrogen-bond donor (HBD) acidities, J. Am. Chem. Soc., 98, 2886, 10.1021/ja00426a036 Kamlet, 1976, The solvatochromic comparison method. I. The.beta.-scale of solvent hydrogen-bond acceptor (HBA) basicities, J. Am. Chem. Soc., 98, 377, 10.1021/ja00418a009 Kamlet, 1983, Linear solvation energy relationships. 23. A comprehensive collection of the solvatochromic parameters,pi.*,alpha., and.beta., and some methods for simplifying the generalized solvatochromic equation, J. Org. Chem., 48, 2877, 10.1021/jo00165a018 Tait, 1984, Infrared study of ambient-temperature chloroaluminates as a function of melt acidity, Inorg. Chem., 23, 4352, 10.1021/ic00193a049 Avent, 1994, Evidence for hydrogen bonding in solutions of 1-ethyl-3-methylimidazolium halides, and its implications for room-temperature halogenoaluminate(III) ionic liquids, J. Chem. Soc., Dalton Trans, 3405, 10.1039/dt9940003405 Fletcher, 2001, Behavior of the solvatochromic probes Reichardt’s dye, pyrene, dansylamide, Nile red and 1-pyrenecarbaldehyde within room-temperature ionic liquid [bmim][PF6], Green Chem., 3, 210, 10.1039/b103592b Dutta, 1996, Spectroscopic studies of nile red in organic solvents and polymers, J. Photochem. Photobiol. A, 93, 57, 10.1016/1010-6030(95)04140-0 Carmichael, 2000, Polarity study of some 1-alkyl 3-methylimidazolium ambient-temperature ionic liquids with the solvatochromic dye, Nile red, J. Phys. Org. Chem., 13, 591, 10.1002/1099-1395(200010)13:10<591::AID-POC305>3.0.CO;2-2 Fletcher, 2002, Solvatochromic Probe Behavior Within Binary Room-Temperature Ionic Liquid 1-Butyl-3-Methyl Imidazolium Hexafluorophosphate Plus Ethanol Solutions, Appl. Spectrosc., 56, 1498, 10.1366/00037020260377823 Berger, 1990, Composition and density effects using methanol/carbon dioxide in packed column supercritical fluid chromatography, Anal. Chem., 62, 1181, 10.1021/ac00210a017 Stuart, 2005, The use of Nile Red to monitor the aggregation behavior in ternary surfactants-water-organic solvent systems, J. Phys. Org. Chem., 18, 929, 10.1002/poc.919 Gautam, 2020, Photophysics and Rotational Dynamics of Nile Red in Room Temperature Ionic Liquid (RTIL) and RTIL-Cosolvents Binary Mixtures, J. Photochem. Photobiol. A, 399, 112550, 10.1016/j.jphotochem.2020.112550 Jessop, 2012, Solvatochromic parameters for solvents of interest in green chemistry, Green Chem., 14, 1245, 10.1039/c2gc16670d Heimer, 2006, Vibrational spectra of imidazolium tetrafluoroborate ionic liquids, J. Mol. Liq., 124, 84, 10.1016/j.molliq.2005.08.004 Holomb, 2008, J. Raman Spectrosc., 39, 793, 10.1002/jrs.1912 Jeon, 2008, J. Phys. Chem. B, 112, 4735, 10.1021/jp7120752 Cha, 2014, Structures of ionic liquid–water mixtures investigated by IR and NMR spectroscopy, Phys. Chem. Chem. Phys., 16, 9591, 10.1039/C4CP00589A Cammarata, 2001, Molecular states of water in room temperature ionic liquids, Phys. Chem. Chem. Phys., 3, 5192, 10.1039/b106900d Arunan, 2011, Definition of the hydrogen bond (IUPAC Recommendations 2011), Pure Appl. Chem., 83, 1637, 10.1351/PAC-REC-10-01-02 Grinvald, 2017, Water Complexes of Ionic Liquids: 1-Butyl-3-methyl Imidazolium Chloride and Tetrafluoroborate Systems in KBr Matrix, ChemistrySelect, 2, 5202, 10.1002/slct.201700613 Grinvald, 2017, Formation of Water Complexes with Organic Compounds in Solid Matter. IR Manifestation and DFT Study, Russ. J. Phys. Chem. A, 91, 2585, 10.1134/S0036024417130106 Grinvald, 2015, IR Manifestation of Water Intermediates Formation with Sodium Hydroxide and Sodium Salts in KBr Matrix, Russ. J. Phys. Chem. A, 89, 2416, 10.1134/S0036024415130166 López-Pastor, 2006, Association of Methanol and Water in Ionic Liquids Elucidated by Infrared Spectroscopy Using Two-Dimensional Correlation and Multivariate Curve Resolution, J. Phys. Chem. B, 110, 10896, 10.1021/jp057398b Redlich, 1948, Thermodynamics of non-electrolyte solutions, x–y–t relations in a binary system, Ind. Eng. Chem., 40, 341, 10.1021/ie50458a035