Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Synthesis and Properties of Pyrrolidinium and Piperidinium Bis(trifluoromethanesulfonyl)imide Ionic Liquids with Allyl Substituents

  • Yim, Tae-Eun (Department of Chemical and Biological Engineering, Research Center for Energy Conversion & Storage, Seoul National University) ;
  • Lee, Hyun-Yeong (Department of Chemical and Biological Engineering, Research Center for Energy Conversion & Storage, Seoul National University) ;
  • Kim, Hyo-Jin (Department of Chemical and Biological Engineering, Research Center for Energy Conversion & Storage, Seoul National University) ;
  • Mun, Jun-Young (Department of Chemical and Biological Engineering, Research Center for Energy Conversion & Storage, Seoul National University) ;
  • Kim, Sang-Mi (Department of Chemical and Biological Engineering, Research Center for Energy Conversion & Storage, Seoul National University) ;
  • Oh, Seung-M. (Department of Chemical and Biological Engineering, Research Center for Energy Conversion & Storage, Seoul National University) ;
  • Kim, Young-Gyu (Department of Chemical and Biological Engineering, Research Center for Energy Conversion & Storage, Seoul National University)
  • Published : 2007.09.20
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Abstract

New pyrrolidinium and piperidinium bis(trifluoromethanesulfonyl)imide (TFSI) ionic liquids (ILs) having allyl substituents were synthesized and characterized. All of them are liquid at room temperature and stable up to 300 oC. The pyrrolidinium-based ILs showed better conductivities and lower viscosities than the corresponding piperidinium-based ILs. Among them, 1-allyl-1-methylpyrrolidinium TFSI showed the lowest viscosity of 52 cP, the highest conductivity of 5.7 mS cm?1, and the most negative cathodic voltage window of ?3.2 V (vs. Fc/Fc+) on a platinum electrode, which are the improved results compared to the corresponding analogue having a saturated substituent, 1-methyl-1-propylpyrrolidinium TFSI.

Keywords

References

  1. Bonhote, P.; Dias, A.-P.; Armand, M.; Papageorgiou, N.; Kalyanasundaram, K.; Gratzel, M. Inorg. Chem. 1996, 35, 1168-1178 https://doi.org/10.1021/ic951325x
  2. Welton, T. Chem. Rev. 1999, 99, 2071-2083 https://doi.org/10.1021/cr980032t
  3. Song, C. E.; Yoon, M. Y.; Choi, D. S. Bull. Korean Chem. Soc. 2005, 26, 1321-1330 https://doi.org/10.5012/bkcs.2005.26.9.1321
  4. Jorapur, Y. R.; Chi, D. Y. Bull. Korean Chem. Soc. 2006, 27, 345-354 https://doi.org/10.5012/bkcs.2006.27.3.345
  5. Kim, S. M.; Kang, Y. K.; Lee, K. S.; Mang, J. Y.; Kim, D. Y. Bull. Korean Chem. Soc. 2006, 27, 423-425 https://doi.org/10.5012/bkcs.2006.27.3.423
  6. Wilkes, J. S.; Zaworotko, M. J. J. Chem. Soc., Chem. Commun. 1992, 965-967
  7. Hagiwara, R.; Ito, Y. J. Fluorine Chem. 2000, 105, 221-227 https://doi.org/10.1016/S0022-1139(99)00267-5
  8. Nishida, T.; Tashiro, Y.; Yamamoto, M. J. Fluorine Chem.2003, 120, 135-141 https://doi.org/10.1016/S0022-1139(02)00322-6
  9. Holbrey, J. D.; Seddon, K. R. J. Chem. Soc., Dalton Trans. 1999, 2133-2139
  10. Webber, A.; Blomgren, G. E. In Advances in Lithium-Ion Batteries; van Schalkwijk, W. A.; Scrosati, B., Eds.; Kluwer Academic/Plenum Publishers: New York, 2002; pp 185-232
  11. In Electrochemical Aspects of Ionic Liquids; Ohno, H., ed.; Wiley-Interscience: Hoboken, 2005; pp 173-223
  12. Garcia, B.; Lavallee, S.; Perron, G.; Michot, C.; Armand, M. Electrochim. Acta 2004, 49, 4583-4588. https://doi.org/10.1016/j.electacta.2004.04.041
  13. Shin, J.; Henderson, W. A.; Scaccia, S.; Prosini, P. P.; Passerini, S. J. Power Sources 2006, 156, 560-566 https://doi.org/10.1016/j.jpowsour.2005.06.026
  14. In Electrochemical Aspects of Ionic Liquids; Ohno, H., ed.; Wiley-Interscience: Hoboken, 2005; pp 173-223
  15. Ue, M.; Takeda, M.; Takahashi, T.; Takehara, M. Electrochem. Solid State Lett. 2002, 5, A119-A121 https://doi.org/10.1149/1.1472255
  16. Balducci, A.; Bardi, U.; Caporali, S.; Mastragostino, M.; Soavi, F. Electrochem. Commun. 2004, 6, 566-570 https://doi.org/10.1016/j.elecom.2004.04.005
  17. Sato, T.; Masuda, G.; Takagi, K. Electrochim. Acta 2004, 49, 3603-3611 https://doi.org/10.1016/j.electacta.2004.03.030
  18. Galinski, M.; Lewandowski, A.; Izabela Stepniak, I. Electrochim. Acta 2006, 51, 5567-5580 https://doi.org/10.1016/j.electacta.2006.03.016
  19. Wang, P.; Zakeeruddin, S. M.; Exnar, I.; Gratzel, M. Chem. Commun. 2002, 2972-2973
  20. Jovanovski, V.; Stathatos, E.; Orel, B.; Lianos, P. Thin Solid Films 2006, 511-512, 634-637
  21. de Souza, R. F.; Padilha, J. C.; Goncalves, R. S.; Dupont, J. Electrochem. Commun. 2003, 5, 728-731 https://doi.org/10.1016/S1388-2481(03)00173-5
  22. Min, G.; Yim, T.; Lee, H. Y.; Huh, D. H.; Lee, E.; Mun, J.; Oh, S. M.; Kim, Y. G. Bull. Korean Chem. Soc. 2006, 27, 847-852 https://doi.org/10.5012/bkcs.2006.27.6.847
  23. MacFarlane, D. R.; Meakin, P.; Sun, J.; Amini, N.; Forsyth, M. J. Phys. Chem. B 1999, 103, 4164-4170 https://doi.org/10.1021/jp984145s
  24. McFarlane, D. R.; Sun, J.; Golding, J.; Meakin, P.; Forsyth, M. Electrochim. Acta 2000, 45, 1271-1278 https://doi.org/10.1016/S0013-4686(99)00331-X
  25. Sakaebe, H.; Matsumoto, H. Electrochem. Commun. 2003, 5, 594-598 https://doi.org/10.1016/S1388-2481(03)00137-1
  26. Barisci, J. N.; Wallace, G. G.; MacFarlane, D. R.; Baughman, R. H. Electrochem. Commun. 2004, 6, 22-27 https://doi.org/10.1016/j.elecom.2003.09.015
  27. Howlett, P. C.; Brack, N.; Hollenkamp, A. F.; Forsyth, M.; MacFarlane, D. R. J. Electrochem. Soc. 2006, 153, A595-A606
  28. Matsumoto, H.; Sakaebe, H.; Tatsumi, K. J. Power Sources 2005, 146, 45-50 https://doi.org/10.1016/j.jpowsour.2005.03.103
  29. Kimbonguila, A. M.; Boucida, S.; Guibe, F.; Loffet, A. Tetrahedron 1997, 53, 12525-12538 https://doi.org/10.1016/S0040-4020(97)00772-2
  30. Sun, J.; MacFarlane, D. R.; Forsyth, M. Electrochim. Acta 2003, 48, 1707-1711 https://doi.org/10.1016/S0013-4686(03)00141-5
  31. Buzzeo, M. C.; Evans, R. G.; Compton, R. G. ChemPhysChem 2004, 5, 1106-1120 https://doi.org/10.1002/cphc.200301017
  32. Lee, J. S.; Bae, J. Y.; Lee, H.; Quan, N. D.; Kim, H. S.; Kim, H. J. Ind. Eng. Chem. 2004, 10, 1086-1089
  33. Anthony, J. L.; Brennecke, J. F.; Holbrey, J. D.; Maginn, E. J.; Mantz, R. A.; Rogers, R. D.; Trulove, P. C.; Visser, A. E.; Welton, T. In Ionic Liquids in Synthesis; Wasserscheid, P.; Welton, T., Eds.; Wiley-VCH Verlag: Weinheim, 2003; pp 41-126
  34. Eliel, E. L.; Wilen, S. H.; Mander, L. N. Stereochemistry of Organic Compounds; Wiley: New York, 1994; pp 686-771
  35. Lee, J.-T.; Lin, Y.-W.; Jan, Y.-S. J. Power Sources 2004, 132, 244-248 https://doi.org/10.1016/j.jpowsour.2004.01.045

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