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High Pressure Study of Rotational Dynamics of Perylene and Sodium 8-methoxypyrene-1,3,6-trisulfonate in Imidazolium-Based Ionic Liquids

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Abstract

Rotation times of perylene and 8-methoxypyrene-1,3,6-trisulfonate (MPTS) in 1-alkyl-3-methylimidazolium tetrafluoroborate and 1-alkyl-3-methylimidazolium hexafluorophosphate under high pressure have been examined by means of time-resolved fluorescence anisotropy measurements. The isothermal compression of sample solutions by the application of high pressure can change the solvent viscosity alone over a wide range, allowing for an observation of the pure viscosity dependence of rotation times at a constant temperature (45 °C). Rotation times of both perylene and MPTS show a considerably nonlinear dependence on the solvent viscosity and a substantial deviation from the predictions of hydrodynamic and quasihydrodynamic theories, particularly at high pressures.

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References

  1. Welton, T.: Room-temperature ionic liquids. Solvents for synthesis and catalysis. Chem. Rev. 99, 2071–2084 (1999)

    Article  CAS  Google Scholar 

  2. Bonhôte, P., Dias, A., Papageorgiou, N., Kalyanasundaram, K., Grätzel, M.: Hydrophobic, highly conductive ambient-temperature molten salts. Inorg. Chem. 35, 1168–1178 (1996)

    Article  Google Scholar 

  3. Plechkova, N., Seddon, K.: Applications of ionic liquids in the chemical industry. Chem. Soc. Rev. 37, 123–150 (2008)

    Article  CAS  Google Scholar 

  4. Fukaya, Y., Hayashi, K., Wada, M., Ohno, H.: Cellulose dissolution with polar ionic liquids under mild conditions: required factors for anions. Green Chem. 10, 44–46 (2008)

    Article  CAS  Google Scholar 

  5. Borra, E.F., Seddiki, O., Angel, R., Eisensein, D., Hickson, P., Seddon, K.R., Worden, S.P.: Metal films deposited on liquids and implications for the lunar liquid mirror telescope. Nature 447, 979–981 (2007)

    Article  CAS  Google Scholar 

  6. Canongia Lopes, J.N.A., Pádua, A.A.H.: Nanostructural organization in ionic liquids. J. Phys. Chem. B 110, 3330–3335 (2006)

    Article  CAS  Google Scholar 

  7. Triolo, A., Russina, O., Bleif, H.-J., Cola, E.D.: Nanoscale segregation in room temperature ionic liquids. J. Phys. Chem. B 111, 4641–4644 (2007)

    Article  CAS  Google Scholar 

  8. Iwata, K., Okajima, H., Saha, S., Hamaguchi, H.: Local structure formation in alkyl-imidazolium-based ionic liquids as revealed by linear and nonlinear Raman spectroscopy. Acc. Chem. Res. 40, 1174–1181 (2007)

    Article  CAS  Google Scholar 

  9. Xiao, D., Rajian, J.R., Hines Jr., L.G., Li, S., Bartsch, R.A., Quitevis, E.L.: Nanostructural organization and anion effects in the optical Kerr effect spectra of binary ionic liquid mixtures. J. Phys. Chem. B 112, 13316–13325 (2008)

    Article  CAS  Google Scholar 

  10. Greaves, T.L., Kennedy, D.F., Mudi, S.T., Drummond, C.J.: Diversity observed in the nanostructure of protic ionic liquids. J. Phys. Chem. B 114, 10022–10031 (2010)

    Article  CAS  Google Scholar 

  11. Russina, O., Triolo, A., Gontrani, L., Caminiti, R.: Mesoscopic structural heterogeneities in room-temperature ionic liquids. J. Phys. Chem. Lett. 3, 27–33 (2012)

    Article  CAS  Google Scholar 

  12. Jin, H., Li, X., Maroncelli, M.: Heterogeneous solute dynamics in room temperature ionic liquids. J. Phys. Chem. B 111, 13473–13478 (2007)

    Article  CAS  Google Scholar 

  13. Liang, M., Kaintz, A., Baker, G.A., Maroncelli, M.: Bimolecular electron transfer in ionic liquids: are reaction rates anomalously high? J. Phys. Chem. B 116, 1370–1384 (2012)

    Article  CAS  Google Scholar 

  14. Karmakar, R., Samanta, A.: Solvation dynamics of coumarin-153 in a room-temperature ionic liquid. J. Phys. Chem. A 106, 4447–4452 (2002)

    Article  CAS  Google Scholar 

  15. Samanta, A.: Dynamic stokes shift and excitation wavelength dependent fluorescence of dipolar molecules in room temperature ionic liquids. J. Phys. Chem. B 110, 13704–13716 (2006)

    Article  CAS  Google Scholar 

  16. Arzhantsev, S., Ito, N., Heitz, M., Maroncelli, M.: Solvation dynamics of coumarin 153 in several classes of ionic liquids: cation dependence of the ultrafast component. Chem. Phys. Lett. 381, 278–286 (2003)

    Article  CAS  Google Scholar 

  17. Ingram, J.A., Moog, R.S., Ito, N., Biswas, R., Maroncelli, M.: Solute rotation and solvation dynamics in a room-temperature ionic liquid. J. Phys. Chem. B 107, 5926–5932 (2003)

    Article  CAS  Google Scholar 

  18. Ito, N., Arzhantsev, S., Heitz, M., Maroncelli, M.: Solvation dynamics and rotation of coumarin 153 in alkylphosphonium ionic liquids. J. Phys. Chem. B 108, 5771–5777 (2004)

    Article  CAS  Google Scholar 

  19. 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. 396, 83–91 (2004)

    Article  CAS  Google Scholar 

  20. Kaintz, A., Baker, G., Benesi, A., Maroncelli, M.: Solute diffusion in ionic liquids, NMR measurements and comparisons to conventional solvents. J. Phys. Chem. B 117, 11697–11708 (2013)

    Article  CAS  Google Scholar 

  21. Mali, K.S., Dutt, G.B., Mukherjee, T.: Do organic solutes experience specific interactions with ionic liquids? J. Chem. Phys. 123, 174504 (2005)

    Article  CAS  Google Scholar 

  22. Mali, K.S., Dutt, G.B., Mukherjee, T.: Rotational diffusion of a nonpolar and a dipolar solute in 1-butyl-3-methylimidazolium hexafluorophosphate and glycerol: interplay of size effects and specific interactions. J. Chem. Phys. 128, 054504 (2008)

    Article  CAS  Google Scholar 

  23. Fruchey, K., Fayer, M.D.: Dynamics in organic ionic liquids in distinct regions using charged and uncharged orientational relaxation probes. J. Phys. Chem. B 114, 2840–2845 (2010)

    Article  CAS  Google Scholar 

  24. Flemming, G.R.: Chemical Application of Ultrafast Spectroscopy. Oxford University Press, New York (1986)

    Google Scholar 

  25. Perrin, F.J.: Mouvement brownien d’un ellipsoide – I. Dispersion diélectrique pour des molécules ellipsoidales. Phys. Radium 5, 497–511 (1934)

    Article  CAS  Google Scholar 

  26. Kivelson, D., Kivelson, M.G., Oppenheim, I.: Rotational relaxation in fluids. J. Chem. Phys. 52, 1810–1821 (1970)

    Article  CAS  Google Scholar 

  27. Minamikawa, Y., Kometani, N.: High-pressure study of solvation properties of room temperature ionic liquids. J. Phys. Conf. Ser. 215, 012067 (2010)

    Article  Google Scholar 

  28. Chryssomallis, G.S., Drickamer, H.G., Weber, G.: The measurement of fluorescence polarization at high pressure. J. Appl. Phys. 49, 3084–3087 (1978)

    Article  CAS  Google Scholar 

  29. Xu, J., Shen, X., Knutson, J.R.: Femtosecond fluorescence upconversion study of the rotations of perylene and tetracene in hexadecane. J. Phys. Chem. A 107, 8383–8387 (2003)

    Article  CAS  Google Scholar 

  30. de Azevedo, R.G., Esperança, J.M.S.S., Najdanovic-Visak, V., Visak, Z.P., Guedes, H.J.R., da Ponte, M.N., Rebelo, L.P.N.: Thermophysical and thermodynamic properties of 1-butyl-3-methylimidazolium tetrafluoroborate and 1-butyl-3-methylimidazolium hexafluorophosphate over an extended pressure range. J. Chem. Eng. Data 50, 997–1008 (2005)

    Article  Google Scholar 

  31. Harris, K.R., Woolf, L.A., Kanakubo, M.: Temperature and pressure dependence of the viscosity of the ionic liquid 1-butyl-3-methylimidazolium hexafluorophosphate. J. Chem. Eng. Data 50, 1777–1782 (2005)

    Article  CAS  Google Scholar 

  32. Harris, K.R., Kanakubo, M., Woolf, L.A.: Temperature and pressure dependence of the viscosity of the ionic liquid 1-butyl-3-methylimidazolium tetrafluoroborate: viscosity and density relationships in ionic liquids. J. Chem. Eng. Data 52, 2425–2430 (2007)

    Article  CAS  Google Scholar 

  33. Ito, N., Kajimoto, O., Hara, K.: High-pressure studies of rotational dynamics for coumarin 153 in alcohols and alkanes. J. Phys. Chem. A 106, 6024–6029 (2002)

    Article  CAS  Google Scholar 

  34. Bauer, D.R., Brauman, I.I., Pecora, R.: Molecular reorientation in liquids. Experimental test of hydrodynamic models. J. Am. Chem. Soc. 96, 6840–6843 (1974)

    Article  CAS  Google Scholar 

  35. Anician, B., Tiffon, B., Dubois, J.E.: 2H nuclear magnetic relaxation study of the rotation of adamantane in n-alkanes. J. Chem. Phys. 74, 5857–5862 (1981)

    Article  Google Scholar 

  36. Stanton, S.G., Pecora, R., Hudson, B.S.: Reorientation of small molecules and anions in solution studied by resonance enhanced dynamic Rayleigh scattering. J. Chem. Phys. 78, 3365–3371 (1983)

    Article  CAS  Google Scholar 

  37. Philips, L.A., Webb, S.P., Clark, J.H.: High-pressure studies of rotational reorientation dynamics: the role of dielectric friction. J. Chem. Phys. 83, 5810–5821 (1985)

    Article  CAS  Google Scholar 

  38. Canonica, S., Schmid, A., Wild, U.P.: The rotational diffusion of p-terphenyl and p-quaterphenyl in non-polar solvents. Chem. Phys. Lett. 122, 529–534 (1985)

    Article  CAS  Google Scholar 

  39. Courtney, S.H., Kim, S.K., Canonica, S., Fleming, G.R.: Rotational diffusion of stilbene in alkane and alcohol solutions. J. Chem. Soc. Faraday Trans. I 82, 2065–2072 (1986)

    Article  CAS  Google Scholar 

  40. Roy, M., Doraiswamy, S.: Rotational dynamics of nonpolar solutes in different solvents: comparative evaluation of the hydrodynamic and quasihydrodynamic models. J. Chem. Phys. 98, 3213–3223 (1993)

    Article  CAS  Google Scholar 

  41. Gierer, A., Wirtz, K.: Molekulare theorie der mikroreibung. Naturforsch. Teil A 8, 532–538 (1953)

    Google Scholar 

  42. Dote, J.L., Kivelson, D., Schwartz, R.N.: The equation of state of hard spheres and the approach to random closest packing. J. Chem. Phys. 88, 1126–1133 (1988)

    Article  Google Scholar 

  43. Anderton, R.M., Kauffman, J.F.: Temperature-dependent rotational relaxation of diphenylbutadiene in n-alcohols: a test of the quasihydrodynamic free space model. J. Phys. Chem. 98, 12117–12124 (1994)

    Article  CAS  Google Scholar 

  44. Antony, J.H., Mertens, D., Dölle, A., Wasserscheid, P., Carper, W.R.: Molecular reorientational dynamics of the neat ionic liquid 1-butyl-3-methylimidazolium hexafluorophosphate by measurement of 13C nuclear magnetic relaxation data. Chem. Phys. Chem. 4, 588–594 (2003)

    CAS  Google Scholar 

  45. Hanke, C.G., Price, S.L., Lynden-Bell, R.M.: Intermolecular potentials for simulations of liquid imidazolium salts. Mol. Phys. 99, 801–809 (2001)

    Article  CAS  Google Scholar 

  46. Madden, P.A., Wilson, M.: Covalent effects in ionic liquids. J. Phys. Condens. Matter 12, A95 (2000)

    Article  CAS  Google Scholar 

  47. Kanakubo, M., Harris, K.R., Tsuchihashi, N., Ibuki, K., Ueno, M.: Effect of pressure on transport properties of the ionic liquid 1-butyl-3-methylimidazolium hexafluorophosphate. J. Phys. Chem. B 111, 2062–2069 (2007)

    Article  CAS  Google Scholar 

  48. Harris, K.R., Kanakubo, M., Tsuchihashi, N., Ibuki, K., Ueno, M.: Effect of pressure on the transport properties of ionic liquids: 1-Alkyl-3-methylimidazolium salts. J. Phys. Chem. B 112, 9830–9840 (2008)

    Article  CAS  Google Scholar 

  49. Harris, K.R.: Relations between the fractional Stokes–Einstein and Nernst–Einstein equations and velocity correlation coefficients in ionic liquids and molten salts. J. Phys. Chem. B 114, 9572–9577 (2010)

    Article  CAS  Google Scholar 

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Kometani, N., Tai, A. High Pressure Study of Rotational Dynamics of Perylene and Sodium 8-methoxypyrene-1,3,6-trisulfonate in Imidazolium-Based Ionic Liquids. J Solution Chem 43, 1529–1538 (2014). https://doi.org/10.1007/s10953-014-0166-3

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