Picosecond Solvation Dynamics of Coumarin153 in Bis(1-methyl-1H-imidazol-3-ium-3-yl)dihydroborate Cation Containing Room Temperature Ionic Liquid and Ionic Liquid-DMF Mixtures

Authors

  • Prabhat Kumar Sahu National Institute of Science Education and Research
  • Sudhir Kumar Das National Institute of Science Education and Research
  • Moloy Sarkar National Institute of Science Education and Research, Bhubaneswar

DOI:

https://doi.org/10.6000/1929-5030.2013.02.01.6

Keywords:

Ionic liquid, Time-dependent Stokes shift, Solvation dynamics, polar cosolvent, Anisotropy

Abstract

Abstract: Steady state and time-resolved fluorescence behavior of coumarin153(C153) in bis(1-methyl-1H-imidazol-3-ium-3-yl)dihydroborate cation containing room temperature ionic liquid and its mixture with dimethylformamide (DMF) has been investigated. Density functional calculations on the present ionic liquid have been carried out to have ground state structural information of this system. C-H···N and C-H···O hydrogen bonding interactions between cationic and anionic moiety of the present ionic liquid has been observed. Steady state absorption and emission spectral profiles of C153 are found not to be influenced by the polar cosolvent. Time-resolved fluorescence anisotropy experiments show that the rotational motion of the probe becomes faster in presence of DMF. During time dependent dynamic Stokes shift measurements in ionic liquid-DMF mixtures, the average solvation time is found to decrease with the addition of DMF to the ionic liquid. The decrease in both average solvation and rotational time of probe molecule upon gradual addition of polar organic co-solvent is attributed to the lowering of bulk viscosity of the medium.

Author Biographies

Prabhat Kumar Sahu, National Institute of Science Education and Research

School of Chemical Sciences

Sudhir Kumar Das, National Institute of Science Education and Research

School of Chemical Sciences

References


[1] Wasserscheid P, Keim W. Ionic liquids: New “solutions” for transition metal catalysis. Angew Chem Int Ed 2000; 39: 3772-89. http://dx.doi.org/10.1002/1521- 3773(20001103)39:21<3772::AID-ANIE3772>3.0.CO;2-5
[2] Rogers RD, Seddon KR. Ionic Liquids-Solvents of the future? Science 2003; 302: 792-3. http://dx.doi.org/10.1126/science.1090313
[3] Ko¨ddermann T, Wertz C, Heintz A, Ludwig R. The association of water in ionic liquids: A reliable measure of polarity. Angew Chem Int Ed 2006; 45: 3697-70. http://dx.doi.org/10.1002/anie.200504471
[4] Samanta A. Dynamic Stokes shift and excitation wavelength dependent fluorescence of dipolar molecules in room temperature ionic liquids. J Phys Chem B 2006; 110: 13704- 6. http://dx.doi.org/10.1021/jp060441q
[5] Samanta A. Solvation dynamics in ionic liquids: What we have learned from the dynamic fluorescence Stokes shift studies. J Phys Chem Lett 2010; 1(10): 1557-62. http://dx.doi.org/10.1021/jz100273b
[6] Paul A, Samanta A. Effect of nonpolar solvents on the solute rotation and solvation dynamics in an imidazolium ionic liquid. J Phys Chem B 2008; 112: 947-53. http://dx.doi.org/10.1021/jp077536s
[7] Ito N, Arzhantsev S, Maroncelli M. The probe dependence of solvation dynamics and rotation in the ionic liquid 1-butyl-3- methyl-imidazolium hexafluorophosphate.Chem Phys Lett 2004; 396: 83-91. http://dx.doi.org/10.1016/j.cplett.2004.08.018
[8] Chakrabarty D, Chakraborty D, Seth D, Hazra P, Sarkar N. Dynamics of solvation and rotational relaxation of Coumarin 153 in 1-butyl-3-methylimidazolium hexafluorophosphate
[bmim]
[PF6]–water mixtures. Chem Phys Lett 2004; 397; 469-74. http://dx.doi.org/10.1016/j.cplett.2004.08.141
[9] Chakrabarty D, Chakraborty D, Seth D, Hazra P, Sarkar N. 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 A 2005; 109; 1764-69. http://dx.doi.org/10.1021/jp0460339
[10] Pramanik R, Rao VG, Sarkar S, Ghatak C, Setua P, Sarkar N. 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 2009; 113: 8626-34. http://dx.doi.org/10.1021/jp900627h
[11] Sarkar S, Pramanik R, Ghatak C, Setua P, Sarkar N. 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 2010; 114: 2779-89. http://dx.doi.org/10.1021/jp907936s
[12] Daschakraborty S, Biswas R. Stokes shift dynamics in (ionic liquid + polar solvent) binary mixtures: Composition dependence. J Phys Chem B 2011; 115: 4011-24. http://dx.doi.org/10.1021/jp200407m
[13] Das SK, Sarkar M. Steady-state and time-resolved fluorescence behavior of coumarin-153 in a hydrophobic ionic liquid and ionic liquid–toluene mixture. J Mol Liq 2012; 165: 38-43. http://dx.doi.org/10.1016/j.molliq.2011.10.004
[14] Gutowski KE, Broker GA. Willauer HD, et al. Controlling the aqueous miscibility of ionic liquids: Aqueous biphasic systems of water-miscible ionic liquids and water-structuring salts for recycle, metathesis, and separations. J Am Chem Soc 2003; 125: 6632-3. http://dx.doi.org/10.1021/ja0351802
[15] Dupont J, de Suza RF, Suarez PAZ. Ionic liquid (molten salt) phase organometallic catalysis. Chem Rev 2002; 102: 3667- 92. http://dx.doi.org/10.1021/cr010338r
[16] GZ Wu, Liu YD, Long DW. Effect of ionic liquid
[Me3NC2H4OH]+
[ZnCl3] - on - radiation polymerization of methylmethacrylate in ethanol and N,N-Dimethylformamde. Macromol Rapid Commun 2005; 26: 57-9. http://dx.doi.org/10.1002/marc.200400375
[17] Dai S, Ju YH, Barnes CE. Solvent extraction of strontium nitrate by a crown ether using room-temperature ionic liquids. Dalton Trans 1999; 1201-2.
[18] Visser AE, Swatloski RP, Reichert WM, Griffin ST, Rogers RD. Traditional extractants in nontraditional solvents: Groups 1 and 2 extraction by crown ethers in room-temperature ionic liquids. Ind Eng Chem Res 2000; 29: 3596-604. http://dx.doi.org/10.1021/ie000426m
[19] Widegen JA, Laesecke A, Magee JW. The effect of dissolved water on the viscosities of hydrophobic room temperature ionic liquids. Chem Commun 2005; 1610-2. http://dx.doi.org/10.1039/b417348a
[20] Fletcher KA, Pandey S. Solvatochromic probe behavior within ternary room-temperature ionic liquid 1-Butyl-3- methylimidazolium Hexafluorophosphate + ethanol + water solutions. J Phys Chem B 2003; 107: 13532-9. http://dx.doi.org/10.1021/jp0276754
[21] Baker SN, Baker GA, Bright FV. Temperature-dependent microscopic solvent properties of ‘dry’and ‘wet’ 1-butyl-3- methylimidazolium hexafluorophosphate: correlation with ET(30) and Kamlet–Taft polarity scales. Green Chem 2002; 4: 165-9. http://dx.doi.org/10.1039/b111285f
[22] Fletcher KA, Pandey S. Solvatochromic probe behavior within binary room-temperature ionic liquid 1-Butyl-3-methyl imidazolium Hexafluorophosphate plus ethanol solutions. Appl Spectrosc 2002; 56: 1498-504. http://dx.doi.org/10.1366/00037020260377823
[23] Harifi-Mood AR, Habibi-Yangjeh A, Gholami MR. Solvatochromic parameters for binary mixtures of 1-(1-Butyl)- 3-methylimidazolium Tetrafluoroborate with some protic molecular solvents. J Phys Chem B 2006; 110: 7073-8. http://dx.doi.org/10.1021/jp0602373
[24] Mellein BR, Aki SNVK, Ladewski RL, Brennecke JF. Effect of water and organic solvents on the ionic dissociation of ionic liquids. J Phys Chem B 2007; 111: 6452-6. http://dx.doi.org/10.1021/jp071051m
[25] Jarosik A, Krajewski SR, Lewandowski A, Radzimski P. Conductivity of ionic liquids in mixtures. J Mol Liq 2006; 123: 43-50. http://dx.doi.org/10.1016/j.molliq.2005.06.001
[26] Tokuda H, Baek SJ, Watanable M. Room-temperature ionic liquid-organic solvent mixture: Conductivity and ion association. Electrochemistry 2005; 73: 620-2.
[27] Z? agar E, Z? igon M. Solution properties of carboxylated polyurethanes and related ionomers in polar solvents (DMF and LiBr/DMF). Polymer 2000; 41: 3513-21. http://dx.doi.org/10.1016/S0032-3861(99)00604-7
[28] Kang YK, Park HS. Internal rotation about the C–N bond of amides. J Mol Struct (Theochem) 2004; 676: 171-6. http://dx.doi.org/10.1016/j.theochem.2004.01.024
[29] Borrmann H, Persson I, Sandstro¨m M, Stålhandske CMV. The crystal and liquid structures of N,Ndimethylthioformamide and N,N-dimethylformamide showing a stronger hydrogen bonding effect for C–H…S than for C– H…O. J Chem Soc Perkin Trans 2 2000; 393-402. http://dx.doi.org/10.1039/a904531g
[30] Umebayashi Y, Matsumoto K, Watanabe M, Ishiguro S. Individual solvation number of first-row transition metal(II) ions in solvent mixtures of N,N-dimethylformamide and N,Ndimethylacetamide-Solvation steric effect. Phys Chem Chem Phys 2001; 3: 5475-81. http://dx.doi.org/10.1039/b107342g
[31] Garc?´a B, Alcalde R, Leal JM, Matos JS. Shear viscosities of the N-methylformamide– and N,N-dimethylformamide–(C1 – C10) alkan-1-ol solvent systems. J Chem Soc Faraday Trans 1997; 93: 1115-8. http://dx.doi.org/10.1039/a607876a
[32] Venkatesu P, Lee MJ, Lin HM. Volumetric properties of (N,Ndimethylformamide + aliphatic diethers) at temperatures ranging from (298.15 to 358.15) K. J Chem Thermodyn 2005; 53: 996-1002. http://dx.doi.org/10.1016/j.jct.2005.01.002
[33] Attri P, Reddy PM, Venkatesu P, Kumar A, Hofman T. Measurements and molecular interactions for N,NDimethylformamide with ionic liquid mixed solvents. J Phys Chem B 2010; 114: 6126-33. http://dx.doi.org/10.1021/jp101209j
[34] Sturlaugson AL, Fruchey KS, Fayer MD. Orientational dynamics of room temperature ionic liquid/water mixtures: Water-induced structure. J Phys Chem B 2012; 116: 1777- 87. http://dx.doi.org/10.1021/jp209942r
[35] Jiang W, Wang Y, Voth GA. Molecular dynamics simulation of nanostructural organization in ionic liquid/water mixtures. J Phys Chem B 2007; 111: 4812-8. http://dx.doi.org/10.1021/jp067142l
[36] Roth C, Appelhagen A, Jobst N, Ludwig R. Microheterogeneities in ionic-liquid–methanol solutions studied by FTIR Spectroscopy, DFT Calculations and molecular dynamics simulations. Chem Phys Chem 2012; 13: 1708-17. http://dx.doi.org/10.1002/cphc.201101022
[37] Raabe G, Köhler J. Thermodynamical and structural properties of binary mixtures of imidazolium chloride ionic liquids and alcohols from molecular simulation. J Chem Phys 2012; 129: 144503-8. http://dx.doi.org/10.1063/1.2990653
[38] Maroncelli M, Fleming GR. Picosecond solvation dynamics of coumarin 153: The importance of molecular aspects of solvation. J Chem Phys 1987; 86: 6221-39. http://dx.doi.org/10.1063/1.452460
[39] Becke DA, Density-functional thermochemistry. III. The role of exact exchange. J Chem Phys 1993; 98: 5648-52. http://dx.doi.org/10.1063/1.464913
[40] Lee C, Yang W, Parr RG. Development of the Colic-Salvetti correlation-energy formula into a functional of the electron density. Phys Rev B 1988; 37: 785-9. http://dx.doi.org/10.1103/PhysRevB.37.785
[41] Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Zakrzewski VG, Montgomery JA, Stratmann RE Jr, 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 Y, Nanayakkara CA, Gonzalez C, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Andres JL, Gonzalez C, Head- Gordon M, Replogle ES, Pople JA, Gaussian 03; RevisionC.02: Gaussian, Inc.: Wallingford, CT 2004.
[42] Rahim Z, Barman BN, Acta Crystallographica A 1978; 34: 761-4. http://dx.doi.org/10.1107/S0567739478001576
[43] Horng ML, Gardecki J, Papazyan A, Maroncelli M. Subpicosecond measurements of polar solvation dynamics: Coumarin 153 revisited. J Phys Chem 1995; 99: 17311-37. http://dx.doi.org/10.1021/j100048a004
[44] Horng ML, Gardecki J, Maroncelli M. Rotational dynamics of Coumarin 153: Time-dependent friction, dielectric friction, and other nonhydrodynamic effects. J Phys Chem A 1997; 101: 1030-47. http://dx.doi.org/10.1021/jp962921v

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2013-03-01

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