Probing the microscopic aspects of 1-butyl-3-methylimidazolium trifluoroacetate ionic liquid and its mixture with water and methanol: A photophysical and theoretical (DFT) study

Journal of Fluorescence

Volumn 23, Issue 6, 2013, Pages 1217-1227

  Das, Sudhir Kumar ^a   Sahu, Prabhat Kumar ^a   Sarkar, Moloy ^a  

^a NATIONAL INSTITUTE OF SCIENCE EDUCATION AND RESEARCH   (India)

Author keywords

Binary mixtures; Excitation wavelength dependence; Fluorescence; Ionic liquids; Structural organization

Indexed keywords

COUPLING CONSTANTS; EXCITATION WAVELENGTH; INTERMOLECULAR INTERACTIONS; MIXED-SOLVENT SYSTEMS; STEADY-STATE ABSORPTION; STRUCTURAL ORGANIZATION; THEORETICAL CALCULATIONS; TIME RESOLVED FLUORESCENCE ANISOTROPY;

BINARY MIXTURES; FLUORESCENCE; ISOMERS; METHANOL; ORGANIC SOLVENTS;

IONIC LIQUIDS;

INSECTIVORA;

EID: 84886802960     PISSN: 10530509     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10895-013-1252-4     Document Type: Article

References (53)

1. Rogers RD, Seddon KR (2002) Ionic liquids industrial applications for green chemistry. Eds.; ACS Symposium Series 818; American Chemical Society: Washington, DC
2. Rogers RD, Seddon KR (2003) Ionic liquids as green solvent. Eds.; ACS Symposium Series 856; American Chemical Society: Washington, DC, Chapter 12
3. Rogers RD, Seddon KR (2005) Ionic Liquids IIIA: Fundamentals, progress, challenges, and opportunities: Properties and structure. Eds.; American Chemical Society: Washington, DC, Vol. 901
4. Judge RA, Takahashi S, Longenecker KL, Fry EH, Zapatero CA, Chiu ML (2009) The effect of ionic liquids on protein crystallization and X-ray diffraction resolution. Cryst Growth Des 9:3463-3469
5. Yao H, Zhang S, Wang J, Zhou Q, Dong H, Zhang X (2012) Densities and viscosities of the binary mixtures of 1-ethyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide with N-methyl-2-pyrrolidone or ethanol at T = (293.15 to 323.15) K. J Chem Eng Data 57:875-881
6. Fletcher KA, Pandey S (2003) Solvatochromic probe behavior within ternary Room-temperature ionic liquid 1-butyl-3-methylimidazolium hexafluorophosphate + ethanol + water solutions. J Phys Chem B 107:13532-13539
7. Widegen JA, Laesecke A, Magee JW (2005) The effect of dissolved water on the viscosities of hydrophobic room-temperature ionic liquids. Chem Commun 1610-1612. doi: 10.1039/b417348a
8. T(30) and Kamlet-Taft polarity scales. Green Chem 4:165-169
9. Harifi-Mood AR, Habibi-Yangjeh A, Gholami MR (2006) Solvatochromic parameters for binary mixtures of 1-(1-butyl)-3-methylimidazolium tetrafluoroborate with some protic molecular solvents. J Phys Chem B 110:7073-7078
10. Ficke LE, Brennecke JF (2010) Interactions of ionic liquids and water. J Phys Chem B 114:10496-10501
11. Jarosik A, Krajewski SR, Lewandowski A (2006) Conductivity of ionic liquids in mixture. J Mol Liq 123:43-50
12. Tokuda H, Baek SJ, Watanable M (2005) Room-temperature ionic liquids-organic solvent association: conductivity and ionic association. Electrochemistry 73:620-622
13. 2O systems: alkyl-group dependence of 1-alkyl-3- methylimidazolium cation. J Phys Chem B 114:6323-6331
14. 2O mixtures. J Phys Chem B 116:13765-13773
15. 6]-water mixtures. Chem Phys Lett 397:469-474
16. Chakrabarty D, Chakraborty A, Seth D, Sarkar N (2005) Effect of water, methanol, and acetonitrile on solvent relaxation and rotational relaxation of coumarin 153 in neat 1-hexyl-3-methylimidazolium hexafluorophosphate. J Phys Chem A109:1764-1769
17. Paul A, Samanta A (2008) Effect of nonpolar solvents on the solute rotation and solvation dynamics in an imidazolium ionic liquid. J Phys Chem B 112:947-953
18. Pramanik R, Rao VG, Sarkar S, Ghatak C, Setua P, Sarkar N (2009) To probe the interaction of methanol and acetonitrile with the ionic liquid N, N, N-trimethyl-N-propyl ammonium bis(trifluoromethanesulfonyl)imide at different temperatures by solvation dynamics study. J Phys Chem B 113:8626-8634
19. Sarkar S, Pramanik R, Ghatak C, Setua P, Sarkar N (2010) Probing the interaction of 1-ethyl-3-methylimidazolium ethyl sulfate ([Emim][EtSO4]) with alcohols and water by solvent and rotational relaxation. J Phys Chem B 114:2779-2789
20. Daschakraborty S, Biswas R (2011) Stokes shift dynamics in (ionic liquid+polar solvent) binary mixtures: composition dependence. J Phys Chem B 115:4011-4024
21. Das SK, Sarkar M (2012) Steady-state and time-resolved fluorescence behavior of coumarin-153 in a hydrophobic ionic liquid and ionic liquid-toluene mixture. J Mol Liq 165:38-43
22. 2 on acetate and trifluoroacetate imidazolium based ionic liquids at high pressures. J Phys Chem B113:6803-6812
23. Shiflett MB, Yokozeki A (2009) Phase behavior of carbon dioxide in ionic liquids: [emim][Acetate],[emim][Trifluoroacetate], and[emim][Acetate]+[emim] [Trifluoroacetate] mixtures. J Chem Eng Data 54:108-114
24. Cammarata L, Kazarian SG, Salterb PA, Welton T (2001) Molecular states of water in room temperature ionic liquids. Phys Chem Chem Phys 3:5192-5200
25. Ito N, Arzhantsev S, Maroncelli M (2004) The probe dependence of solvation dynamics and rotation in the ionic liquid 1-butyl-3-methyl-imidazolium hexafluorophosphate. Chem Phys Lett 396:83-91
26. Jin H, Baker GA, Arzhantsev S, Dong J, Maroncelli M (2007) Solvation and rotational dynamics of coumarin 153 in ionic liquids: comparisons to conventional solvents. J Phys Chem B 111:7291-7302
27. Li B, Wang Y, Wang X, Vdovic S, Guo Q, Xia A (2012) Spectroscopic evidence for unusual microviscosity in imidazolium ionic liquid and tetraethylene glycol dimethyl ether cosolvent mixtures. J Phys Chem B 116:13272-13281
28. Maroncelli M, Fleming GR (1987) Picosecond solvation dynamics of coumarin 153: the importance of molecular aspects of solvation. J Chem Phys 86:6221
29. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Zakrzewski VG, Montgomery JA Jr, Stratmann RE, Burant JC, Dapprich S, Millam JM, Daniels AD, Kudin KN, Strain MC, Farkas O, Tomasi J, Barone V, Cossi M, Cammi R, Mennucci B, Pomelli C, Adamo C, Clifford S, Ochterski J, Petersson GA, Ayala PY, Cui Q, Morokuma K, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Cioslowski J, Ortiz JV, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Gomperts R, Martin RL, Fox DJ, Keith T, Al Laham MA, Peng CY, Nanayakkara A, Gonzalez C, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Andres JL, Gonzalez C, Head-Gordon M, Replogle ES, Pople JA (2004) Gaussian 03, Revision C.02. Gaussian, Inc, Wallingford
30. Zhang QG, Wang NN, Yu ZW (2010) The hydrogen bonding Interactions between the ionic liquid 1-ethyl-3-methylimidazolium ethyl sulfate and water. J Phys Chem B 114:4747-4754
31. Wang NN, Zhang QG, Wu FG, Li QZ, Yu ZW (2010) Hydrogen bonding interactions between a representative pyridinium-based ionic liquid [BuPy][BF4] and water/dimethyl sulfoxide. J Phys Chem B 114:8689-8700
32. Zhang Q-G, Wang N-N, Wang S-L, Yu Z-W (2011) Hydrogen bonding behaviors of binary systems containing the ionic liquid 1-butyl-3-methylimidazolium trifluoroacetate and water/methanol. J Phys Chem B 115:11127-11136
33. Urahata SM, Ribeiro MCC (2004) J Chem Phys 120(4):1855-1863
34. Wang Y, Voth GA (2005) Unique spatial heterogeneity in ionic liquids. J Am Chem Soc 127:12192-12193
35. Lopes JNAC, Padua AAH (2006) Nanostructural organization in ionic liquids. J Phys Chem B 110:3330-3335
36. Lopes JNC, Gomes MFC, Padua AAH (2006) Nonpolar, polar, and associating solutes in ionic liquids. J Phys Chem B 110:16816-16818
37. Wang YT, Voth GA (2006) Tail aggregation and domain diffusion in ionic liquids. J Phys Chem B 110:18601-18608
38. Mandal PK, Sarkar M, Samanta A (2004) Excitation-wavelength-dependent fluorescence behavior of some dipolar molecules in room-temperature ionic liquids. J Phys Chem A 108:9048-9053
39. Jin H, Li X, Maroncelli M (2007) Heterogeneous solute dynamics in room temperature ionic liquids. J Phys Chem B 111:13473-13478
40. Adhikari A, Sahu K, Dey S, Ghosh S, Mandal U, Bhattacharyya K (2007) Femtosecond solvation dynamics in a neat ionic liquid and ionic liquid microemulsion: excitation wavelength dependence. J Phys Chem B 111:12809-12816
41. Das SK, Sarkar M (2012) Solvation and rotational relaxation of coumarin 153 in a new hydrophobic ionic liquid: an excitation wavelength dependence study. J Lumin 132:368-374
42. Das SK, Sarkar M (2012) Studies on the solvation dynamics of coumarin 153 in 1-ethyl-3-methylimidazolium alkylsulfate ionic liquids: dependence on alkyl chain length. ChemPhysChem 13:2761-2768
43. Das SK, Sahu PK, Sarkar M (2013) Diffusion-viscosity decoupling in solute rotation and solvent relaxation of coumarin153 in ionic liquids containing Fluoroalkylphosphate (FAP) anion: a thermophysical and photophysical study. J Phys Chem B 117:636-647
44. Patra S, Samanta A (2012) Microheterogeneity of some imidazolium ionic liquids as revealed by fluorescence correlation spectroscopy and lifetime studies. J Phys Chem B 116:12275-12283
45. Pal T, Biswas R (2011) Heterogeneity and viscosity decoupling in (acetamide + electrolyte) molten mixtures: a model simulation study. Chem Phys Lett 517:180-185
46. Guchhait B, Daschakraborty S, Biswas R (2012) Medium decoupling of dynamics at temperatures ∼100 K above glass-transition temperature: a case study with (acetamide + lithium bromide/nitrate) melts. J Chem Phys 136:11847
47. Valeur B, Weber G (1977) Anisotropic rotations in 1-naphthylamine. Existence of a red-edge transition moment normal to the ring plane. Chem Phys Lett 45:140-144
48. Weber G, Shinitzky M (1970) Failure of energy transfer between identical aromatic molecules on excitation at the long wave edge of the absorption spectrum. Proc Natl Acad Sci U S A 65:823-830
49. Hu CM, Zwanzig R (1974) Rotational friction coefficients for spheroids with the slipping boundary condition. J Chem Phys 60:4354
50. Das SK, Sarkar M (2012) Rotational dynamics of coumarin-153 and 4-aminophthalimide in1-ethyl-3-methylimidazolium alkylsulfate ionic liquids: effect of alkyl chain length on the rotational dynamics. J Phys Chem B 116:194-202
51. Horng M-L, Gardecki J, Maroncelli M (1997) Rotational dynamics of coumarin 153: time-dependent friction, dielectric friction, and other nonhydrodynamic effects. J Phys Chem A 101:1030-1047
52. Bondi A (1964) van der Waals Volumes and Radii. J Phys Chem 68:441-451
53. Rahim Z, Barman BN (1978) The van der Waals Criterion for hydrogen bonding. Acta Crystallogr A 34:761-764