Room-Temperature Zwitterionic Ionic Liquids
DOI:
https://doi.org/10.17721/fujcV4I1P85-94Keywords:
zwitterionic ionic liquids, urocanic acid, imidazoliumAbstract
A novel series of zwitterionic ionic liquids based on (E) or (Z) isomer of an urocanic moiety containing a carboxylate group have been prepared. All synthesized compounds present melting points below 100°C. This value can be easily tuned by changing the length of alkyl chain grafted on the imidazolium moiety and the nature of isomer. Hence, melting temperature as low as -20°C was obtained for Z isomer with a N1, N3-methyloctyl imidazolium moiety.
References
Austen Angell C, Ansari Y, Zhao Z. Ionic Liquids: Past, present and future. Faraday Discuss. 2012;154:9-27. https://doi.org/10.1039/c1fd00112d
Wilkes, J. S., Wasserscheid, P. and Welton, T. (2007) Introduction, in Ionic Liquids in Synthesis, Second Edition (eds P. Wasserscheid and T. Welton), Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, Germany. https://doi.org/10.1002/9783527621194
Ionic Liquids: Applications and Perspectives Edited by Alexander Kokorin, ISBN 978-953-307-248-7, 686 pages, Publisher: InTech https://doi.org/10.5772/1782
Quartarone E, Mustarelli P. Electrolytes for solid-state lithium rechargeable batteries: recent advances and perspectives. Chemical Society Reviews 2011;40(5):2525. https://doi.org/10.1039/c0cs00081g
Devanathan R. Recent developments in proton exchange membranes for fuel cells. Energy & Environmental Science 2008;1(1):101. https://doi.org/10.1039/b808149m
Yoshizawa M, Hirao M, Ito-Akita K, Ohno H. Ion conduction in zwitterionic-type molten salts and their polymers. Journal of Materials Chemistry 2001;11(4):1057-1062. https://doi.org/10.1039/b101079o
Yoshizawa-Fujita M, Tamura T, Takeoka Y, Rikukawa M. Low-melting zwitterion: effect of oxyethylene units on thermal properties and conductivity. Chem. Commun. 2011;47(8):2345-2347. https://doi.org/10.1039/c0cc03754k
Yoshizawa M, Ohno H. Anhydrous proton transport system based on zwitterionic liquid and HTFSI. Chemical Communications 2004;(16):1828. https://doi.org/10.1039/b404137b
Nguyen D, Hwang J, Lee J, Kim H, Lee H, Cheong M, Lee B, Kim H. Multi-functional zwitterionic compounds as additives for lithium battery electrolytes. Electrochemistry Communications 2007;9(1):109-114. https://doi.org/10.1016/j.elecom.2006.08.045
Fei Z, Zhao D, Geldbach T, Scopelliti R, Dyson P. Brønsted Acidic Ionic Liquids and Their Zwitterions: Synthesis, Characterization and pKa Determination. Chemistry - A European Journal 2004;10(19):4886-4893. https://doi.org/10.1002/chem.200400145
Lissner E, de Souza W, Ferrera B, Dupont J. Oxidative Desulfurization of Fuels with Task-Specific Ionic Liquids. ChemSusChem 2009;2(10):962-964. https://doi.org/10.1002/cssc.200900171
Nockemann P, Thijs B, Pittois S, Thoen J, Glorieux C, Van Hecke K, Van Meervelt L, Kirchner B, Binnemans K. Task-Specific Ionic Liquid for Solubilizing Metal Oxides. The Journal of Physical Chemistry B 2006;110(42):20978-20992. https://doi.org/10.1021/jp0642995
Lin J, Huang C, Lee Y, Lee K, Lin I. Carboxylic acid functionalized imidazolium salts: sequential formation of ionic, zwitterionic, acid-zwitterionic and lithium salt-zwitterionic liquid crystals. Journal of Materials Chemistry 2011;21(22):8110. https://doi.org/10.1039/c1jm10580a
Fei Z, Zhao D, Geldbach T, Scopelliti R, Dyson P. Brønsted Acidic Ionic Liquids and Their Zwitterions: Synthesis, Characterization and pKa Determination. Chemistry - A European Journal 2004;10(19):4886-4893. https://doi.org/10.1002/chem.200400145
Holbrey J, Reichert W, Tkatchenko I, Bouajila E, Walter O, Tommasi I, Rogers R. 1,3-Dimethylimidazolium-2-carboxylate: the unexpected synthesis of an ionic liquid precursor and carbene-CO2 adductElectronic supplementary information (ESI) available: experimental data for 1,3-dimethylimidazolium-2-carboxylate. Supplemental crystal structure data. ORTEP, hydrogen bonding and packing diagrams. See http://www.rsc.org./suppdata/cc/b2/b211519k/. Chemical Communications 2002;(1):28-29. https://doi.org/10.1039/b211519k
Mehler A, Tabor H. Isolation of N-formyl-L-glutamic acid as an intermediate in the enzymatic degradation of L-histidine. J Biol Chem. 1953;201:775-785.
Tabachnick J. Urocanic acid, the major acid-soluble, ultraviolet-absorbing compound in guinea pig epidermis. Archives of Biochemistry and Biophysics 1957;70(1):295-298. https://doi.org/10.1016/0003-9861(57)90107-8
Anglin JH. Urocanic acid, a natural sunscreen. Cosmet and toiletries 1976;91:47-49.
Lattes A, Lauth-de Vinguerie N, Sergueeva N, Damiot M, Mawlawi H, Riviere M. Selective N-Alkylation of (E)-Urocanic Acid. HETEROCYCLES 1994;37(3):1561. https://doi.org/10.3987/com-93-s111
Downloads
Published
Issue
Section
License
Authors who publish with this journal agree to the following terms:
Authors retain copyright and grant the journal right of first publication with the work simultaneously licensed under a Creative Commons Attribution License that allows others to share the work with an acknowledgement of the work's authorship and initial publication in this journal.
Authors are able to enter into separate, additional contractual arrangements for the non-exclusive distribution of the journal's published version of the work (e.g., post it to an institutional repository or publish it in a book), with an acknowledgement of its initial publication in this journal.
Authors are permitted and encouraged to post their work online (e.g., in institutional repositories or on their website) prior to and during the submission process, as it can lead to productive exchanges, as well as earlier and greater citation of published work (See The Effect of Open Access).