Static and transport properties of alkyltrimethylammonium cation-based room-temperature ionic liquids

Journal of Physical Chemistry B

Volumn 118, Issue 17, 2014, Pages 4590-4599

  Seki, Shiro ^a   Tsuzuki, Seiji ^b   Hayamizu, Kikuko ^b   Serizawa, Nobuyuki ^a   Ono, Shimpei ^a   Takei, Katsuhito ^a   Doi, Hiroyuki ^c   Umebayashi, Yasuhiro ^c  

^a CENTRAL RESEARCH INSTITUTE OF ELECTRIC POWER INDUSTRY   (Japan)

^b NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY AIST   (Japan)

^c NIIGATA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMMONIUM COMPOUNDS; COMPUTATIONAL METHODS; DIFFUSION IN LIQUIDS; MOLECULAR DYNAMICS; POSITIVE IONS; REFRACTIVE INDEX; TRANSPORT PROPERTIES;

EXPERIMENTAL METHODS; MOLECULAR DYNAMICS SIMULATIONS; NUCLEAR MAGNETIC RESONANCE TECHNIQUES; PHYSICOCHEMICAL PROPERTY; PULSED GRADIENT SPIN ECHOS; ROOM TEMPERATURE IONIC LIQUIDS; SELF-DIFFUSION COEFFICIENTS; STATIC PROPERTIES;

IONIC LIQUIDS;

EID: 84899784479     PISSN: 15206106     EISSN: 15205207     Source Type: Journal    
DOI: 10.1021/jp500123q     Document Type: Article

References (90)

1. Wilkes, J. S.; Zaworotko, M. J. Air and Water Stable 1-Ethyl-3- Methylimidazolium Based Ionic Liquids J. Chem. Soc., Chem. Commun. 1992, 965-967
2. Welton, T. Room-Temperature Ionic Liquids. Solvents for Synthesis and Catalysis Chem. Rev. 1999, 99, 2071-2084
3. Earle, M. J.; Esperanca, J. M. S. S.; Gilea, M. A.; Lopes, J. N. C.; Rebelo, L. P. N.; Magee, J. W.; Seddon, K. R.; Widegren, J. A. The Distillation and Volatility of Ionic Liquids. Nature 2006, 439, 831-834.
4. 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
5. Sakaebe, H.; Matsumoto, H. N -Methyl- N -Propylpiperidinium Bis(trifluoromethanesulfonyl)imide (PP13-TFSI)-Novel Electrolyte Base for Li Battery Electrochem. Commun. 2003, 5, 594-598
6. Nakagawa, H.; Izuchi, S.; Kuwana, K.; Nukuda, T.; Aihara, Y. Liquid and Polymer Gel Electrolytes for Lithium Batteries Composed of Room-Temperature Molten Salt Doped by Lithium Salt J. Electrochem. Soc. 2003, 150, A695-A700
7. Garcia, B.; Lavallee, S.; Perron, G.; Michot, C.; Armand, M. Room Temperature Molten Salts as Lithium Battery Electrolyte Electrochim. Acta 2004, 49, 4583-4588
8. Tiyapiboonchaiya, C.; Pringle, J. M.; Sun, J.; Byrne, N.; Howlett, P. C.; MacFarlane, D. R.; Forsyth, M. The Zwitterion Effect in High-Conductivity Polyelectrolyte Materials Nat. Mater. 2004, 3, 29-32
9. Shin, J.-H.; Henderson, W. A.; Passerini, S. An Elegant Fix for Polymer Electrolytes Electrochem. Solid-State Lett. 2005, 8, A125-A127
10. Hayashi, K.; Nemoto, Y.; Akuto, K.; Sakurai, Y. Alkylated Imidazolium Salt Electrolyte for Lithium Cells J. Power Sources 2005, 146, 689-692
11. Seki, S.; Kobayashi, Y.; Miyashiro, H.; Ohno, Y.; Usami, A.; Mita, Y.; Kihira, N.; Watanabe, M.; Terada, N. Lithium Secondary Batteries Using Modified-Imidazolium Room-Temperature Ionic Liquid J. Phys. Chem. B 2006, 110, 10228-10230
12. Seki, S.; Kobayashi, Y.; Miyashiro, H.; Ohno, Y.; Mita, Y.; Terada, N.; Charest, P.; Guerfi, A.; Zaghib, K. Compatibility of N -Methyl- N -Propylpyrrolidinium Cation Room-Temperature Ionic Liquid Electrolytes and Graphite Electrodes J. Phys. Chem. C 2008, 112, 16708-16713
13. Kuang, D.; Wang, P.; Ito, S.; Zakeeruddin, S. M.; Gratzel, M. Stable Mesoscopic Dye-Sensitized Solar Cells Based on Tetracyanoborate Ionic Liquid Electrolyte J. Am. Chem. Soc. 2006, 128, 7732-7733
14. Kato, T.; Kado, T.; Tanaka, S.; Okazaki, A.; Hayase, S. Quasi-Solid Dye-Sensitized Solar Cells Containing Nanoparticles Modified with Ionic Liquid-Type Molecules J. Electrochem. Soc. 2006, 153, A626-A630
15. Kawano, R.; Matsui, H.; Matsuyama, C.; Sato, A.; Susan, M. A. B. H.; Tanabe, N.; Watanabe, M. High Performance Dye-sensitized Solar Cells Using Ionic Liquids as Their Electrolytes J. Photochem. Photobiol., A 2004, 164, 87-92
16. Ue, M.; Takeda, M.; Toriumi, A.; Kominato, A.; Hagiwara, R.; Ito, Y. Application of Low-Viscosity Ionic Liquid to the Electrolyte of Double-Layer Capacitors J. Electrochem. Soc. 2003, 150, A499-A502
17. Matsumoto, K.; Hagiwara, R. Electrochemical Properties of the Ionic Liquid 1-Ethyl-3-methylimidazolium Difluorophosphate as an Electrolyte for Electric Double-Layer Capacitors J. Electrochem. Soc. 2010, 157, A578-A581
18. Seki, S.; Serizawa, N.; Hayamizu, K.; Tsuzuki, S.; Umebayashi, Y.; Takei, K.; Miyashiro, H. Physicochemical and Electrochemical Properties of 1-Ethyl-3-Methylimidazolium Tris(pentafluoroethyl)trifluorophosphate and 1-Ethyl-3-Methylimidazolium Tetracyanoborate J. Electrochem. Soc. 2012, 159, A967-A971
19. Doyle, M.; Choi, S. K.; Proulx, G. High-Temperature Proton Conducting Membranes Based on Perfluorinated Ionomer Membrane-Ionic Liquid Composites J. Electrochem. Soc. 2000, 147, 34-37
20. Noda, A.; Susan, M. A. B. H.; Kudo, K.; Mitsushima, S.; Hayamizu, K.; Watanabe, M. Brønsted Acid-Base Ionic Liquids as Proton-Conducting Nonaqueous Electrolytes J. Phys. Chem. B 2003, 107, 4024-4033
21. Hagiwara, R.; Nohira, T.; Matsumoto, K.; Tamba, Y. A Fluorohydrogenate Ionic Liquid Fuel Cell Operating Without Humidification Electrochem. Solid-State Lett. 2005, 8, A231-A233
22. Navarra, M. A.; Panero, S.; Scrosati, B. Novel, Ionic-Liquid-Based, Gel-Type Proton Membranes Electrochem. Solid-State Lett. 2005, 8, A324-A327
23. Ono, S.; Seki, S.; Hirahara, R.; Tominari, Y.; Takeya, J. High-mobility, Low-power, and Fast-switching Organic Field-effect Transistors with Ionic Liquids Appl. Phys. Lett. 2008, 92, 103313-1-3
24. Uemura, T.; Hirahara, R.; Tominari, Y.; Ono, S.; Seki, S.; Takeya, J. Electronic Functionalization of Solid-to-Liquid Interfaces between Organic Semiconductors and Ionic Liquids: Realization of Very High Performance Organic Single-Crystal Transistors Appl. Phys. Lett. 2008, 93, 263305-1-3
25. Ono, S.; Miwa, K.; Seki, S.; Takeya, J. A Comparative Study of Organic Single-Crystal Transistors Gated with Various Ionic-liquid Electrolytes Appl. Phys. Lett. 2009, 94, 063301
26. Seki, S.; Kobayashi, T.; Kobayashi, Y.; Takei, K.; Miyashiro, H.; Hayamizu, K.; Tsuzuki, S.; Mitsugi, T.; Umebayashi, Y. Effects of Cation and Anion on Physical Properties of Room-temperature Ionic Liquids J. Mol. Liq. 2010, 152, 9-13
27. Seki, S.; Tsuzuki, S.; Hayamizu, K.; Umebayashi, Y.; Serizawa, N.; Takei, K.; Miyashiro, H. Comprehensive Refractive Index Property for Room-Temperature Ionic Liquids J. Chem. Eng. Data 2012, 57, 2211-2216
28. Frech, R.; Petrowsky, M. Molecular Model of Self Diffusion in Polar Organic Liquids: Implications for Conductivity and Fluidity in Polar Organic Liquids and Electrolytes J. Phys. Chem. B 2014, 118, 2422-2432
29. Petrowsky, M.; Burba, C. M.; Frech, R. Mass and Charge Transport in 1-Alkyl-3-Methylimidazolium Triflate Ionic Liquids J. Chem. Phys. 2013, 139, 204502-1-5
30. Seki, S.; Umebayashi, Y.; Tsuzuki, S.; Hayamizu, K.; Kobayashi, Y.; Ohno, Y.; Kobayashi, T.; Mita, Y.; Miyashiro, H.; Terada, N. Phase Transition and Conductive Acceleration of Phosphonium-Cation-Based Room-temperature Ionic Liquid Chem. Commun. 2008, 5541-5543
31. 2 J. Phys. Chem. B 1999, 103, 519-524
32. 4 J. Phys. Chem. B 2004, 108, 19527-19532
33. 19F NMR Studies on Diffusion Coefficients and Local Motions J. Phys. Chem. B 2008, 112, 1189-1197
34. 19F NMR J. Phys. Chem. A 2008, 112, 12027-12036
35. http://www.kishida.co.jp/product/catalog/list/category/139.
36. Stejskal, E. O. Use of Spin Echoes in a Pulsed Magnetic-Field Gradient to Study Anisotropic Restricted Diffusion and Flow J. Phys. Chem. 1965, 43, 3597-3603
37. Isshiki, M.; Ohishi, Y.; Goto, S.; Takeshita, K.; Ishikawa, T. High-energy X-ray Diffraction Beamline: BL04B2 at SPring-8 Nucl. Instrum. Methods Phys. Res., Sect. A 2001, 467-468, 663-666
38. Kohara, S.; Suzuya, K.; Kashihara, Y.; Matsumoto, N.; Umesaki, N.; Sakai, I. A Horizontal Two-axis Diffractometer for High-energy X-ray Diffraction Using Synchrotron Radiation on Bending Magnet Beamline BL04B2 at SPring-8 Nucl. Instrum. Methods Phys. Res., Sect. A 2001, 467-468, 1030-1033
39. Sasaki, S. KEK Report 90-16; National Laboratory for High Energy Physics: Japan, 1991.
40. Hubbell, J. H.; Veigele, W. J.; Briggs, E. A.; Brown, R. T.; Cromer, D. T.; Howerton, R. J. Atomic Form Factors, Incoherent Scattering Functions, and Photon Scattering Cross Sections J. Phys. Chem. Ref. Data 1975, 4, 471-538
41. Cromer, D. T. Compton Scattering Factors for Aspherical Free Atoms J. Chem. Phys. 1969, 50, 4857-4859
42. Cromer, D. T.; Mann, J. B. Compton Scattering Factors for Spherically Symmetric Free Atoms J. Chem. Phys. 1967, 47, 1892-1983
43. Maslen, E. N.; Fox, A. G.; O'Keefe, M. A. International Tables For Crystallography Vol. C; Kluwer: Dordrecht, The Netherlands, 1999; pp 572-574.
44. Johansson, G.; Sandström, M. Computer Programs for the Analysis of Data on X-ray Diffraction by Liquids Chem. Scripta 1973, 4, 195-199
45. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, Jr., J. A.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Gaussian 03, Revision E.01; Gaussian, Inc.: Wallingford, CT, 2004.
46. http://staff.aist.go.jp/w.shinoda/index.html.
47. Allen, M. P.; Tildesley, D. J. Computer Simulation of Liquids; Clarendon Press: Oxford, U.K., 1987.
48. Tsuzuki, S.; Shinoda, W.; Saito, H.; Mikami, M.; Tokuda, H.; Watanabe, M. Molecular Dynamics Simulations of Ionic Liquids: Cation and Anion Dependence of Self-Diffusion Coefficients of Ions J. Phys. Chem. B 2009, 113, 10641-10649
49. Tsuzuki, S.; Matsumoto, H.; Shinoda, W.; Mikami, M. Effects of Conformational Flexibility of Alkyl Chains of Cations on Diffusion of Ions in Ionic Liquids Phys. Chem. Chem. Phys. 2011, 13, 5987-5993
50. Lopes, J. N. A. C.; Deschamps, J.; Padua, A. A. H. Modeling Ionic Liquids Using a Systematic All-Atom Force Field J. Phys. Chem. B 2004, 108, 2038-2047
51. Lopes, J. N. A. C.; Padua, A. A. H. Molecular Force Field for Ionic Liquids Composed of Triflate or Bistriflylimide Anions J. Phys. Chem. B 2004, 108, 16893-16898
52. Lopes, J. N. A. C.; Padua, A. A. H. Molecular Force Field for Ionic Liquids III: Imidazolium, Pyridinium, and Phosphonium Cations; Chloride, Bromide, and Dicyanamide Anions J. Phys. Chem. B 2006, 110, 19586-19592
53. Lopes, J. N. A. C.; Padua, A. A. H.; Shimizu, K. Molecular Force Field for Ionic Liquids IV: Trialkylimidazolium and Alkoxycarbonyl-Imidazolium Cations; Alkylsulfonate and Alkylsulfate Anions J. Phys. Chem. B 2008, 112, 5039-5046
54. Singh, U. C.; Kollman, P. A. An Approach to Computing Electrostatic Charges for Molecules J. Comput. Chem. 1984, 5, 129-145
55. Besler, B. H.; Merz, K. M.; Kollman, P. A. Atomic Charges Derived from Semiempirical Methods J. Comput. Chem. 1990, 11, 431-439
56. Tokuda, H.; Hayamizu, K.; Ishii, K.; Susan, M. A. B. H.; Watanabe, M. Physicochemical Properties and Structures of Room Temperature Ionic Liquids. 2. Variation of Alkyl Chain Length in Imidazolium Cation J. Phys. Chem. B 2005, 109, 6103-6110
57. Vogel, H. Temperatur Unabhängigkeitsgesetz der Viskosität von Flüssigkeiten Phys. Z. 1921, 22, 645-646
58. Tamman, G.; Hesse, W. Die Abhängigkeit der Viscosität von der Temperatur bie unterkühlten Flüssigkeiten Z. Anorg. Allg. Chem. 1926, 156, 245-257
59. Fulcher, G. S. Analysis of Recent Measurements of the Viscosity of Glasses J. Am. Ceram. Soc. 1923, 8, 339-355
60. Williams, M. L.; Landel, R. F.; Ferry, J. D. The Temperature Dependence of Relaxation Mechanisms in Amorphous Polymers and Other Glass-Forming Liquids J. Am. Chem. Soc. 1955, 77, 3701-3707
61. Sato, T.; Maruo, T.; Marukane, S.; Takagi, K. Ionic Liquids Containing Carbonate Solvent as Electrolytes for Lithium Ion Cells J. Power Sources 2004, 138, 253-261
62. Sato, T.; Masuda, G.; Takagi, K. Electrochemical Properties of Novel Ionic Liquids for Electric Double Layer Capacitor Applications Electrochim. Acta 2004, 49, 3603-3611
63. Seki, S.; Kobayashi, Y.; Miyashiro, H.; Ohno, Y.; Mita, Y.; Usami, A.; Terada, N.; Watanabe, M. Reversibility of Lithium Secondary Batteries Using a Room-Temperature Ionic Liquid Mixture and Lithium Metal Electrochem. Solid-State Lett. 2005, 8, A577-A578
64. Seki, S.; Ohno, Y.; Miyashiro, H.; Kobayashi, Y.; Usami, A.; Mita, Y.; Terada, N.; Hayamizu, K.; Tsuzuki, S.; Watanabe, M. Quaternary Ammonium Room-Temperature Ionic Liquid/Lithium Salt Binary Electrolytes: Electrochemical Study J. Electrochem. Soc. 2008, 155, A421-A427
65. Tsunashima, K.; Sugiya, M. Physical and Electrochemical Properties of Low-viscosity Phosphonium Ionic Liquids as Potential Electrolytes Electrochem. Commun. 2007, 9, 2353-2358
66. Tsunashima, K.; Sugiya, M. Physical and Electrochemical Properties of Room Temperature Ionic Liquids Based on Quaternary Phosphonium Cations Electrochemistry 2007, 75, 734-736
67. Xu, W.; Cooper, E. I.; Angell, C. A. Ionic Liquids: Ion Mobilities, Glass Temperatures, and Fragilities J. Phys. Chem. B 2003, 107, 6170-6178
68. Ue, M. Mobility and Ionic Association of Lithium and Quaternary Ammonium Salts in Propylene Carbonate and γ-Butyrolactone J. Electrochem. Soc. 1994, 141, 3336-3342
69. - and Applicability of Stokes Law to Its Propylene Carbonate Solution J. Electrochem. Soc. 1996, 143, L270-L272
70. Ue, M.; Murakami, A.; Nakamura, S. A Convenient Method to Estimate Ion Size for Electrolyte Materials Design J. Electrochem. Soc. 2002, 149, A1385-A1388
71. 13) Cation and Bis(trifluoromethanesulfonyl)amide and Bis(fluorosulfonyl)amide Anions and Their Binary Systems Including Lithium Salts J. Chem. Phys. 2010, 133, 194505-1-13
72. Hayamizu, K.; Tsuzuki, S.; Seki, S.; Umebayashi, Y. NMR Studies on the Rotational and Translational Motions of Ionic Liquids Composed of 1-Ethyl-3-Methylimidazolium (EMIm) Cation and Bis(trifluoromethanesulfonyl)amide (TFSA) and Bis(fluorosulfonyl)amide (FSA) Anions and Their Binary Systems Including Lithium Salts J. Chem. Phys. 2011, 135, 084505-1-11
73. 4 Anion J. Phys. Chem. B 2012, 116, 11284-11291
74. Hayamizu, K. Translational and Rotational Motions for TFSA-Based Ionic Liquids Studied by NMR Spectroscopy; Handy, S. T., Ed.; InTech: Shanghai, 2011.
75. 19F NMR Ionic Diffusion Coefficient, Viscosity, and Ionic Conductivity of Non-Chloroaluminate Room-Temperature Ionic Liquids J. Phys. Chem. B 2001, 105, 4603-4610
76. Tokuda, H.; Hayamizu, K.; Ishii, K.; Susan, M. A. B. H.; Watanabe, M. Physicochemical Properties and Structures of Room Temperature Ionic Liquids. 1. Variation of Anionic Species J. Phys. Chem. B 2004, 108, 16593-16600
77. Tokuda, H.; Ishii, K.; Susan, M. A. B. H.; Tsuzuki, S.; Hayamizu, K.; Watanabe, M. Physicochemical Properties and Structures of Room-Temperature Ionic Liquids. 3. Variation of Cationic Structures J. Phys. Chem. B 2006, 110, 2833-2839
78. Tokuda, H.; Tsuzuki, S.; Susan, M. A. B. H.; Hayamizu, K.; Watanabe, M. How Ionic Are Room-Temperature Ionic Liquids? An Indicator of the Physicochemical Properties J. Phys. Chem. B 2006, 110, 19593-19600
79. Tsuzuki, S.; Tokuda, H.; Hayamizu, K.; Watanabe, M. Magnitude and Directionality of Interaction in Ion Pairs of Ionic Liquids: Relationship with Ionic Conductivity J. Phys. Chem. B 2005, 109, 16474-16481
80. Lopes, J. N. C.; Gomes, M. F. C.; Pa'dua, A. A. H. Nonpolar, Polar, and Associating Solutes in Ionic Liquids J. Phys. Chem. B 2006, 110, 16816-16818
81. Rebelo, L. P. N.; Lopes, J. N. C.; Esperanca, J. M. S. S.; Guedes, H. J. R.; Lachwa, J.; Najdanovic-Visak, V.; Visak, Z. P. Accounting for the Unique, Doubly Dual Nature of Ionic Liquids from a Molecular Thermodynamic and Modeling Standpoint Acc. Chem. Res. 2007, 40, 1114-1121
82. Lopes, J. N. C.; Pádua, A. A. H. Nanostructural Organization in Ionic Liquids J. Phys. Chem. B 2006, 110, 3330-3335
83. Triolo, A.; Russina, O.; Bleif, H.-J.; Cola, E. D. Nanoscale Segregation in Room Temperature Ionic Liquids J. Phys. Chem. B 2007, 111, 4641-4644
84. Umebayashi, Y.; Hamano, H.; Tsuzuki, S.; Lopes, J. N. C.; Pádua, A. A. H.; Kameda, Y.; Kohara, S.; Yamaguchi, T.; Fujii, K.; Ishiguro, S. Dependence of the Conformational Isomerism in 1- n -Butyl-3-methylimidazolium Ionic Liquids on the Nature of the Halide Anion J. Phys. Chem. B 2010, 114, 11715-11724
85. + Ion Solvation in Bis(trifluoromethanesulfonyl)amide Based Ionic Liquids Composed of 1-Ethyl-3-Methylimidazolium and N -Methyl- N -Propylpyrrolidinium Cations J. Phys. Chem. B 2011, 115, 12179-12191
86. Fujii, K.; Kanzaki, R.; Takamuku, T.; Kameda, Y.; Kohara, S.; Kanakubo, M.; Shibayama, M.; Ishiguro, S.; Umebayashi, Y. Experimental Evidences for Molecular Origin of Low-Q Peak in Neutron/X-ray Scattering of 1-Alkyl-3-Methylimidazolium Bis(trifluoromethanesulfonyl)amide Ionic Liquids J. Chem. Phys. 2011, 135, 244502-1-11
87. Song, X.; Hamano, H.; Minofar, B.; Kanzaki, R.; Fujii, K.; Kameda, Y.; Kohara, S.; Watanabe, M.; Ishiguro, S.; Umebayashi, Y. Structural Heterogeneity and Unique Distorted Hydrogen Bonding in Primary Ammonium Nitrate Ionic Liquids Studied by High-Energy X-ray Diffraction Experiments and MD Simulations J. Phys. Chem. B 2012, 116, 2801-2813
88. Matsugami, M.; Fujii, K.; Ueki, T.; Kitazawa, Y.; Umebayashi, Y.; Watanabe, M.; Shibayama, M. Specific Solvation of Benzyl Methacrylate in 1-Ethyl-3-methylimidazolium Bis(trifluoromethanesulfonyl)amide Ionic Liquid Anal. Sci. 2013, 29, 311-314
89. Russina, O.; Triolo, A. New Experimental Evidence Supporting the Mesoscopic Segregation Model in Room Temperature Ionic Liquids Faraday Discuss. 2012, 154, 97-109
90. Kashyap, H. K.; Santos, C. S.; Annapureddy, H. V. R.; Sanjeeva, M. N.; Margulis, C. J.; Castner, E. W., Jr. Temperature-dependent Structure of Ionic Liquids: X-ray Scattering and Simulations Faraday Discuss. 2012, 154, 133-143