Solvatochromic probe response within ionic liquids and their equimolar mixtures with tetraethylene glycol

Journal of Physical Chemistry B

Volumn 118, Issue 38, 2014, Pages 11259-11270

  Rai, Rewa ^a   Pandey, Siddharth ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY DELHI   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EQUIMOLAR MIXTURES; SOLVATOCHROMIC PROBES; TETRAETHYLENE GLYCOLS;

EID: 84907459072     PISSN: 15206106     EISSN: 15205207     Source Type: Journal    
DOI: 10.1021/jp504165a     Document Type: Article

References (48)

1. Rogers, R. D.; Seddon, K. R., Eds. Ionic Liquids III: Fundamentals, Challenges, and Opportunities; ACS Symposium Series 901; American Chemical Society: Washington, DC, 2005.
2. Rogers, R. D.; Seddon, K. R. Ionic Liquids - Solvents of the Future? Science 2003, 302, 792-793
3. Welton, T. Room-Temperature Ionic Liquids. Solvents for Synthesis and Catalysis Chem. Rev. 1999, 99, 2071-2084
4. Wasserscheid, P.; Keim, W. Ionic Liquids-New ″Solutions″ for Transition Metal Catalysis Angew. Chem., Int. Ed. 2000, 39, 3772-3789
5. Baker, G. A.; Baker, S. N.; Pandey, S.; Bright, F. V. An analytical view of ionic liquids Analyst 2005, 130, 800-808
6. Anderson, J.; Armstrong, D. W. Immobilized Ionic Liquids as High-Selectivity/High-Temperature/High-Stability Gas Chromatography Stationary Phases Anal. Chem. 2005, 77, 6453-6462
7. Armand, M.; Endres, F.; MacFarlane, D. R.; Ohno, H.; Scrosati, B. Ionic-liquid materials for the electrochemical challenges of the future Nat. Mater. 2009, 8, 621-629
8. Lee, J. S.; Wang, X.; Luo, H.; Baker, G. A.; Dai, S. Facile Ionothermal Synthesis of Microporous and Mesoporous Carbons from Task Specific Ionic Liquids J. Am. Chem. Soc. 2009, 131, 4596-4597
9. Malhotra, S. Ionic Liquid Applications: Pharmaceuticals, Therapeutics, and Biotechnology; ACS Symposium Series; American Chemical Society: Washington, DC, 2010.
10. Ho, T. D.; Canestraro, A. J.; Anderson, J. L. Ionic Liquids in Solid-Phase Microextraction: A review Anal. Chim. Acta 2011, 695, 18-43
11. Barber, P. S.; Griggs, C. S.; Gurau, G.; Liu, Z.; Li, S.; Li, Z.; Lu, X.; Zhang, S.; Rogers, R. D. Coagulation of Chitin and Cellulose from 1-Ethyl-3-methylimidazolium Acetate Ionic-Liquid Solutions using Carbon Dioxide Angew. Chem., Int. Ed. 2013, 52, 12350-12353
12. Seddon, K. R.; Stark, A.; Torres, M.-J. Influence of Chloride, Water, and Organic Solvents on the Physical Properties of Ionic Liquids Pure Appl. Chem. 2000, 72, 2275-2287
13. Aki, S. N. V. K.; Brennecke, J. F.; Samanta, A. How polar are room-temperature ionic liquids? Chem. Commun. 2001, 413-414
14. Swatloski, R. P.; Visser, A. E.; Reichert, W. M.; Broker, G. A.; Farina, L. M.; Holbrey, J. D.; Rogers, R. D. On the Solubilization of Water with Ethanol in Hydrophobic Hexafluorophosphate Ionic Liquid Green Chem. 2002, 4, 81-87
15. Swatloski, R. P.; Visser, A. E.; Reichert, W. M.; Broker, G. A.; Farina, L. M.; Holbrey, J. D.; Rogers, R. D. Solvation of 1-Butyl-3-methylimidazolium Hexafluorophosphate in Aqueous Ethanol-A Green Solution for Dissolving 'Hydrophobic' Ionic Liquids Chem. Commun. 2001, 20, 2070-2071
16. Chen, J.; Spear, S. K.; Huddleston, J. G.; Rogers, R. D. Polyethylene Glycol and Solutions of Polyethylene Glycol as Green Reaction Media Green Chem. 2005, 7, 64-82
17. Sarkar, A.; Trivedi, S.; Baker, G. A.; Pandey, S. Multiprobe Spectroscopic Evidence for "Hyperpolarity" within 1-Butyl-3-methylimidazolium Hexafluorophosphate Mixtures with Tetraethylene Glycol J. Phys. Chem. B 2008, 112, 14927-14936
18. Sarkar, A.; Trivedi, S.; Pandey, S. Polymer Molecular Weight-Dependent Unusual Fluorescence Probe Behavior within 1-Butyl-3-methylimidazolium Hexafluorophosphate + Poly(ethylene glycol) J. Phys. Chem. B 2009, 113, 7606-7614
19. Rodríguez, H.; Francisco, M.; Rahman, M.; Sun, N.; Rogers, R. D. Biphasic Liquid Mixtures of Ionic Liquids and Polyethylene Glycols Phys. Chem. Chem. Phys. 2009, 11, 10916-10922
20. Sit, P. S.; Bolikal, D.; Melman, J. H.; Treiser, M. D.; Kohn, J. Surface Modification with a New Silanated Tetraethylene Glycol for Biotechnological Applications. Abstracts of Papers, 227th ACS National Meeting, Anaheim, CA, Mar 28-Apr 1, 2004; American Chemical Society: Washington, DC, 2004.
21. Downard, A. J.; Mohamed, A. B. Suppression of Protein Adsorption at Glassy Carbon Electrodes Covalently Modified with Tetraethylene Glycol Diamine Electroanalysis 1999, 11, 418-423
22. Burrell, A. K.; Del Sesto, R. E.; Baker, S. N.; McCleskey, T. M.; Baker, G. A. The Large Scale Synthesis of Pure Imidazolium and Pyrrolidinium Ionic Liquids Green Chem. 2007, 9, 449-454
23. T(33), A Solvatochromic Polarity and Micellar Probe for Neutral Aqueous Solutions Phys. Chem. Liq. 1989, 50, 51-56
24. Tada, E. B.; Novaki, L. P.; El Seoud, O. A. Solvatochromism in Pure and Binary Solvent Mixtures: Effects of the Molecular Structure of the Zwitterionic Probe J. Phys. Org. Chem. 2000, 13, 679-687
25. Handy, S. T.; Okello, M. The 2 Position of Imidazolium Ionic Liquids: Substitution and Exchange J. Org. Chem. 2005, 70, 1915-1918
26. Huang, M.-M.; Jiang, Y.; Sasisanker, P.; Driver, G. W.; Weingärtner, H. Static Relative Dielectric Permittivities of Ionic Liquids at 25 °C J. Chem. Eng. Data 2011, 56, 1494-1499
27. Krossing, I.; Slattery, J. M.; Daguenet, C.; Dyson, P. J.; Oleinikova, A.; Weingärtner, H. Why Are Ionic Liquids Liquid? A Simple Explanation Based on Lattice and Solvation Energies J. Am. Chem. Soc. 2006, 128, 13427-13434
28. Bright, F. V.; Baker, G. A. Comment on 'How Polar Are Ionic Liquids? Determination of the Static Dielectric Constant of an Imidazolium-based Ionic Liquid by Microwave Dielectric Spectroscopy J. Phys. Chem. B 2006, 110, 5822-5823
29. Lide, D. R.; Frederikse, H. P. R., Eds. CRC Handbook of Chemistry and Physics, 77 th ed.; CRC Press: New York, 1996.
30. Kamlet, M. J.; Abboud, J. L.; Taft, R. W. The Solvatochromic Comparison Method. 6. The π∗ Scale of Solvent Polarities J. Am. Chem. Soc. 1977, 99, 6027-6038
31. Kamlet, M. J.; Taft, R. W. The Solvatochromic Comparison Method. I. The β-Scale of Solvent Hydrogen-Bond Acceptor (HBA) Basicities J. Am. Chem. Soc. 1976, 98, 377-383
32. Taft, R. W.; Kamlet, M. J. The Solvatochromic Comparison Method. 2. The α-Scale of Solvent Hydrogen-Bond Donor (HBD) Acidities J. Am. Chem. Soc. 1976, 98, 2886-2894
33. Jessop, P. G.; Jessop, D. A.; Fu, D.; Phan, L. Solvatochromic Parameters for Solvents of Interest in Green Chemistry Green Chem. 2012, 14, 1245-1259
34. Minisci, F.; Porta, O. Advances in Homolytic Substitution of Heteroaromatic Compounds Adv. Heterocycl. Chem. 1974, 16, 123-180
35. Cláudio, A. F. M.; Swift, L.; Hallett, J. P.; Welton, T.; Coutinhoa, J. A. P.; Freire, M. G. Extended Scale for the Hydrogen-Bond Basicity of Ionic Liquids Phys. Chem. Chem. Phys. 2014, 16, 6593-6601
36. Street, K. W., Jr.; Acree, W. E., Jr.; Shetty, P. H.; Poole, C. F. Benzo(ghi)perylene Versus Pyrene as Solute Probes for Polarity Determination of Liquid Organic Salts Used in Chromatography Analyst 1988, 113, 1869-1871
37. Karpovich, D. S.; Blanchard, G. J. Relating the Polarity Dependent Fluorescence Response of Pyrene to Vibronic Coupling. Achieving a Fundamental Understanding of the Py Polarity Scale J. Phys. Chem. 1995, 99, 3951-3958
38. Kalyanasundaram, K.; Thomas, J. K. Environmental Effects on Vibronic Band Intensities in Pyrene Monomer Fluorescence and Their Application in Studies of Micellar Systems J. Am. Chem. Soc. 1977, 99, 2039-2044
39. Acree, W. E., Jr.; Wilkins, D. C.; Tucker, S. A.; Griffin, J. M.; Powell, J. R. Spectrochemical Investigations of Preferential Solvation. Part 2. Compatibility of Thermodynamic Models Versus Spectrofluorometric Probe Methods for Tautomeric Solutes Dissolved in Binary Mixtures J. Phys. Chem. 1994, 98, 2537-2544
40. 6Green Chem. 2001, 3, 210-215
41. Fletcher, K. A.; Baker, S. N.; Baker, G. A.; Pandey, S. Probing Solute and Solvent Interactions within Binary Ionic Liquid Mixtures New J. Chem. 2003, 27, 1706-1712
42. Kosower, E. M.; Dodiuk, H.; Tanizawa, K.; Ottolenghi, M.; Orbach, N. Intramolecular Donor-Acceptor Systems. Radiative and Nonradiative Processes for the Excited States of 2-N-Arylamino-6-naphthalenesulfonate J. Am. Chem. Soc. 1975, 97, 2167-2178
43. Stryer, L. Fluorescence Spectroscopy of Proteins Science 1968, 162, 526-533
44. Acree., W. E., Jr. Absorption and Luminescence Probes. In Encyclopedia of Analytical Chemistry: Theory and Instrumentation; Meyer, R. A., Ed.; John Wiley & Sons, Ltd.: Chichester, 2000.
45. Weber, G.; Farris, F. J. Synthesis and Spectral Properties of a Hydrophobic Fluorescent Probe: 6-Propionyl-2-(dimethylamino)naphthalene Biochemistry 1979, 18, 3075-3078
46. Everett, R. K.; Nguyen, H. A. A.; Abelt, C. J. Does PRODAN Possess an O-TICT Excited State? Synthesis and Properties of Two Constrained Derivatives J. Phys. Chem. A 2010, 114, 4946-4950
47. Valeur, B.; Berberan-Santos, M. N. Molecular Fluorescence: Principles and Applications, 2 nd ed.; Wiley-VCH: Weinheim, 2012; Chapter 13.
48. Marini, A.; Muñoz-Losa, A.; Biancardi, A.; Mennucci, B. What is Solvatochromism? J. Phys. Chem. B 2010, 114, 17128-17135