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Phosphonium-Based Ionic Liquids: An Overview

Fraser, Kevin J., MacFarlane, Douglas R.·2009·Australian Journal of Chemistry

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Abstract

Phosphonium cation-based ionic liquids (ILs) are a readily available family of ILs that in some applications offer superior properties as compared to nitrogen cation-based ILs. Applications recently investigated include their use as extraction solvents, chemical synthesis solvents, electrolytes in batteries and super-capacitors, and in corrosion protection. At the same time the range of cation–anion combinations available commercially has also been increasing in recent years. Here, we provide an overview of the properties of these interesting materials and the applications in which they are appearing.

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A low-cost, high-efficiency solar cell based on dye-sensitized colloidal TiO2 films
O'Regan, B., & Grätzel, M. (1991) · Nature · doi:10.1038/353737a0 · Cited by 28,599
Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds
Miyaura, N., & Suzuki, A. (1995) · Chemical Reviews · doi:10.1021/cr00039a007 · Cited by 12,817
Room-Temperature Ionic Liquids: Solvents for Synthesis and Catalysis. 2
Hallett, J. P., & Welton, T. (2011) · Chemical Reviews · doi:10.1021/cr1003248 · Cited by 12,578
Room-Temperature Ionic Liquids. Solvents for Synthesis and Catalysis
Welton, T. (1999) · Chemical Reviews · doi:10.1021/cr980032t · Cited by 11,852
Ionic Liquids—New “Solutions” for Transition Metal Catalysis
Wasserscheid, P., & Keim, W. (2000) · Angewandte Chemie · doi:10.1002/1521-3773(20001103)39:21<3772::aid-anie3772>3.0.co;2-5 · Cited by 5,720
Electrochemical Supercapacitors : Scientific Fundamentals and Technological Applications
Conway, B. E. (2013) · CERN Document Server (European Organization for Nuclear Research) · Cited by 5,015
Carbon materials for the electrochemical storage of energy in capacitors
Frackowiak, E., & Béguin, F. (2001) · Carbon · doi:10.1016/s0008-6223(00)00183-4 · Cited by 4,523
Ionic Liquids in Synthesis
(2002) · Wiley eBooks · doi:10.1002/3527600701 · Cited by 3,960
Characterization and comparison of hydrophilic and hydrophobic room temperature ionic liquids incorporating the imidazolium cation
Huddleston, J. G., Visser, A. E., Reichert, W. M., Willauer, H. D., Broker, G. A., & Rogers, R. D. (2001) · Green Chemistry · doi:10.1039/b103275p · Cited by 3,712
Catalytic reactions in ionic liquids.
Sheldon, R. A. (2001) · Chemical Communications · doi:10.1039/b107270f · Cited by 2,672
Influence of chloride, water, and organic solvents on the physical properties of ionic liquids
Seddon, K. R., Stark, A., & Torres, M.-J. (2000) · Pure and Applied Chemistry · doi:10.1351/pac200072122275 · Cited by 2,293
Palladium-catalyzed vinylic hydrogen substitution reactions with aryl, benzyl, and styryl halides
Heck, R. F., & Nolley, J. P. (1972) · The Journal of Organic Chemistry · doi:10.1021/jo00979a024 · Cited by 2,202
Ionic Liquids for Clean Technology
Seddon, K. R. (1997) · Journal of Chemical Technology & Biotechnology · doi:10.1002/(sici)1097-4660(199704)68:4<351::aid-jctb613>3.0.co;2-4 · Cited by 2,034
Physicochemical Properties and Structures of Room Temperature Ionic Liquids. 2. Variation of Alkyl Chain Length in Imidazolium Cation
Tokuda, H., Hayamizu, K., Ishii, K., Susan, M. A. B. H., & Watanabe, M. (2005) · The Journal of Physical Chemistry B · doi:10.1021/jp044626d · Cited by 1,707
Physicochemical Properties and Structures of Room Temperature Ionic Liquids. 1. Variation of Anionic Species
Tokuda, H., Hayamizu, K., Ishii, K., Susan, M. A. B. H., & Watanabe, M. (2004) · The Journal of Physical Chemistry B · doi:10.1021/jp047480r · Cited by 1,337
Use of Ionic Liquids for π-Conjugated Polymer Electrochemical Devices
Lu, W., Fadeev, A. G., Qi, B., Smela, E., Mattes, B. R., Ding, J., Spinks, G. M., Mazurkiewicz, J., Zhou, D., Wallace, G. G., et al. (2002) · Science · doi:10.1126/science.1072651 · Cited by 1,185
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Xu, W., Cooper, E. I., & Angell, C. A. (2003) · The Journal of Physical Chemistry B · doi:10.1021/jp0275894 · Cited by 1,062
Ionic liquids: applications in catalysis
Zhao, D., Wu, M., Kou, Y., & Min, E. (2002) · Catalysis Today · doi:10.1016/s0920-5861(01)00541-7 · Cited by 1,049
Pulsed-Gradient Spin−Echo 1H and 19F NMR Ionic Diffusion Coefficient, Viscosity, and Ionic Conductivity of Non-Chloroaluminate Room-Temperature Ionic Liquids
Noda, A., Hayamizu, K., & Watanabe, M. (2001) · The Journal of Physical Chemistry B · doi:10.1021/jp004132q · Cited by 1,022
Ionic Liquids by Proton Transfer: Vapor Pressure, Conductivity, and the Relevance of Δp Ka from Aqueous Solutions
Yoshizawa, M., Xu, W., & Angell, C. A. (2003) · Journal of the American Chemical Society · doi:10.1021/ja035783d · Cited by 946
Physicochemical Properties and Structures of Room-Temperature Ionic Liquids. 3. Variation of Cationic Structures
Tokuda, H., Ishii, K., Susan, M. A. B. H., Tsuzuki, S., Hayamizu, K., & Watanabe, M. (2006) · The Journal of Physical Chemistry B · doi:10.1021/jp053396f · Cited by 849
Electrochemical Properties of Imidazolium Salt Electrolytes for Electrochemical Capacitor Applications
McEwen, A. B., Ngo, H. L., LeCompte, K., & Goldman, J. L. (1999) · Journal of The Electrochemical Society · doi:10.1149/1.1391827 · Cited by 845
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Papageorgiou, N., Athanassov, Y., Armand, M., Bonho⁁te, P., Pettersson, H., Azam, A., & Grätzel, M. (1996) · Journal of The Electrochemical Society · doi:10.1149/1.1837171 · Cited by 739
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Matsumoto, H., Sakaebe, H., Tatsumi, K., Kikuta, M., Ishiko, E., & Kono, M. (2006) · Journal of Power Sources · doi:10.1016/j.jpowsour.2006.02.018 · Cited by 572
Pure ionic liquid electrolytes compatible with a graphitized carbon negative electrode in rechargeable lithium-ion batteries
Ishikawa, M., Sugimoto, T., Kikuta, M., Ishiko, E., & Kono, M. (2006) · Journal of Power Sources · doi:10.1016/j.jpowsour.2006.02.077 · Cited by 549
Industrial preparation of phosphonium ionic liquidsPortions of this work were presented at the following meetings: (a) 224th American Chemical Society Conference, Boston, USA, 2002; (b) Green Solvents for Catalysis Meeting, held in Bruchsal, Germany, 13–16th October 2002.
Bradaric, C. J., Downard, A., Kennedy, C., Robertson, A. J., & Zhou, Y. (2003) · Green Chemistry · doi:10.1039/b209734f · Cited by 546
High efficiency dye-sensitized nanocrystalline solar cells based on ionic liquid polymer gel electrolyte
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See all 536

Authors: Fraser, K. J., & MacFarlane, D. R.
Venue: Australian Journal of Chemistry
Publisher: CSIRO Publishing
Published: 2009-04-24
Volume: 62
Issue: 4
Pages: 309-321
ISSN: 0004-9425 (ISSN-L)
1445-0038
DOI: 10.1071/ch08558
OpenAlex: W1975298007
Cited by: 536
References: 68
FWCI: 8.64
Type: journal article
Language: en
Open access: closed

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Phosphonium-Based Ionic Liquids: An Overview

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