Surface-Active Ionic Liquids in Catalytic Water Splitting
Alice Cognigni A , Ádám Márk Palvögyi A , Christian Schröder B , Herwig Peterlik C , Alexander R. M. Müllner C , Ronald Zirbs D , Matthias Weil E and Katharina Bica A FA Institute of Applied Synthetic Chemistry, Vienna University of Technology, Getreidemarkt 9/163, 1060 Vienna, Austria.
B University of Vienna, Faculty of Chemistry, Department of Computational Biological Chemistry, Währingerstrasse 17, 1090 Vienna, Austria.
C Faculty of Physics, University of Vienna, Boltzmanngasse 5, A-1090 Vienna, Austria.
D Institute for Biologically Inspired Materials, Department of Nanobiotechnology (DNBT), University of Natural Resources and Life Sciences, Vienna, Muthgasse 11-II, 1190 Vienna, Austria.
E Institute for Chemical Technologies and Analytics, Vienna University of Technology, Getreidemarkt 9/164, 1060 Vienna, Austria.
F Corresponding author. Email: katharina.schroeder@tuwien.ac.at
Australian Journal of Chemistry 72(2) 34-41 https://doi.org/10.1071/CH18104
Submitted: 10 March 2018 Accepted: 29 April 2018 Published: 18 July 2018
Abstract
We report the application of surface-active ionic liquids as ligands and optional reaction media in iridium-catalyzed water oxidations. Three novel catalysts with N,N-dialkylimidazolidin-2-ylidene ligands based on amphiphilic imidazolium ionic liquids were synthesized and characterized. Excellent turn-over frequencies of up to 0.92 s−1 were obtained in catalytic water splitting, and activity was maintained for five consecutive catalytic cycles, with an overall turn-over number of 8967. The addition of external surface-active ionic liquid showed unexpected behaviour, because strongly enhanced initial reaction rates were observed.
References
[1] M. D. Kärkäs, O. Verho, E. V. Johnston, B. Åkermark, Chem. Rev. 2014, 114, 11863.| Crossref | GoogleScholarGoogle Scholar |
[2] J. D. Blakemore, R. H. Crabtree, G. W. Brudvig, Chem. Rev. 2015, 115, 12974.
| Crossref | GoogleScholarGoogle Scholar |
[3] N. D. McDaniel, F. J. Coughlin, L. L. Tinker, S. Bernhard, J. Am. Chem. Soc. 2008, 130, 210.
| Crossref | GoogleScholarGoogle Scholar |
[4] J. D. Blakemore, N. D. Schley, D. Balcells, J. F. Hull, G. W. Olack, C. D. Incarvito, O. Eisenstein, G. W. Brudvig, R. H. Crabtree, J. Am. Chem. Soc. 2010, 132, 16017.
| Crossref | GoogleScholarGoogle Scholar |
[5] J. F. Hull, D. Balcells, J. D. Blakemore, C. D. Incarvito, O. Eisenstein, G. W. Brudvig, R. H. Crabtree, J. Am. Chem. Soc. 2009, 131, 8730.
| Crossref | GoogleScholarGoogle Scholar |
[6] D. G. H. Hetterscheid, J. N. H. Reek, Chem. Commun. 2011, 2712.
| Crossref | GoogleScholarGoogle Scholar |
[7] A. Petronilho, M. Rahman, J. A. Woods, H. Al-Sayyed, H. Müller-Bunz, J. M. Don MacElroy, S. Bernhard, M. Albrecht, Dalton Trans. 2012, 13074.
| Crossref | GoogleScholarGoogle Scholar |
[8] J. A. Woods, R. Lalrempuia, A. Petronilho, N. D. McDaniel, H. Müller-Bunz, M. Albrecht, S. Bernhard, Energy Environ. Sci. 2014, 7, 2316.
| Crossref | GoogleScholarGoogle Scholar |
[9] T. P. Brewster, J. D. Blakemore, N. D. Schley, C. D. Incarvito, N. Hazari, G. W. Brudvig, R. H. Crabtree, Organometallics 2011, 30, 965.
| Crossref | GoogleScholarGoogle Scholar |
[10] O. Diaz-Morales, T. J. P. Hersbach, D. G. H. Hetterscheid, J. N. H. Reek, M. T. M. Koper, J. Am. Chem. Soc. 2014, 136, 10432.
| Crossref | GoogleScholarGoogle Scholar |
[11] A. Volpe, A. Sartorel, C. Tubaro, L. Meneghini, M. Di Valentin, C. Graiff, M. Bonchio, Eur. J. Inorg. Chem. 2014, 2014, 665.
| Crossref | GoogleScholarGoogle Scholar |
[12] I. Corbucci, A. Petronilho, H. Müller-Bunz, L. Rocchigiani, M. Albrecht, A. Macchioni, ACS Catal. 2015, 5, 2714.
| Crossref | GoogleScholarGoogle Scholar |
[13] S. Chen, S. Zhang, X. Liu, J. Wang, J. Wang, K. Dong, J. Sun, B. Xu, Phys. Chem. Chem. Phys. 2014, 16, 5893.
| Crossref | GoogleScholarGoogle Scholar |
[14] R. Hayes, G. G. Warr, R. Atkin, Chem. Rev. 2015, 115, 6357.
| Crossref | GoogleScholarGoogle Scholar |
[15] J. Bowers, C. P. Butts, P. J. Martin, M. C. Vergara-Gutierrez, R. K. Heenan, Langmuir 2004, 20, 2191.
| Crossref | GoogleScholarGoogle Scholar |
[16] Y. Kohno, H. Ohno, Chem. Commun. 2012, 48, 7119.
| Crossref | GoogleScholarGoogle Scholar |
[17] J. Łuczak, J. Hupka, J. Thòming, C. Jungnickel, Colloids Surf. A 2008, 329, 125.
| Crossref | GoogleScholarGoogle Scholar |
[18] C. Jungnickel, J. Łuczak, J. Ranke, J. F. Fernández, A. Müller, J. Thöming, Colloids Surf. A 2008, 316, 278.
| Crossref | GoogleScholarGoogle Scholar |
[19] M. Blesic, M. H. Marques, N. V. Plechkova, K. R. Seddon, L. P. N. Rebelo, A. Lopes, Green Chem. 2007, 9, 481.
| Crossref | GoogleScholarGoogle Scholar |
[20] S. Friesen, T. Buchecker, A. Cognigni, K. Bica, R. Buchner, Langmuir 2017, 33, 9844.
| Crossref | GoogleScholarGoogle Scholar |
[21] T. Inoue, H. Ebina, B. Dong, L. Zheng, J. Colloid Interface Sci. 2007, 314, 236.
| Crossref | GoogleScholarGoogle Scholar |
[22] B. Šarac, Ž. Medoš, A. Cognigni, K. Bica, L.-J. Chen, M. Bešter-Rogač, Colloids Surf. A 2017, 532, 609.
| Crossref | GoogleScholarGoogle Scholar |
[23] J. P. Hallett, T. Welton, Chem. Rev. 2011, 111, 3508.
| Crossref | GoogleScholarGoogle Scholar |
[24] Ionic Liquid-Based Surfactant Science: Formulation, Characterization, and Applications (Eds B. K. Paul, S. P. Moulik) 2015 (John Wiley: Hoboken, NJ).
[25] M. Vasiloiu, P. Gaertner, R. Zirbs, K. Bica, Eur. J. Org. Chem. 2015, 2015, 2374.
| Crossref | GoogleScholarGoogle Scholar |
[26] A. Cognigni, P. Gaertner, R. Zirbs, H. Peterlik, K. Prochazka, C. Schröder, K. Bica, Phys. Chem. Chem. Phys. 2016, 18, 13375.
| Crossref | GoogleScholarGoogle Scholar |
[27] M. Cokoja, R. M. Reich, M. E. Wilhelm, M. Kaposi, J. Schäffer, D. S. Morris, C. J. Münchmeyer, M. H. Anthofer, I. I. E. Markovits, F. E. Kühn, W. A. Herrmann, A. Jess, J. B. Love, ChemSusChem 2016, 9, 1773.
| Crossref | GoogleScholarGoogle Scholar |
[28] R. Sharma, B. Gupta, T. Yadav, S. Sinha, A. K. Sahu, Y. Karpichev, N. Gathergood, J. Marek, K. Kuca, K. K. Ghosh, ACS Sustain. Chem.& Eng. 2016, 4, 6962.
| Crossref | GoogleScholarGoogle Scholar |
[29] J. Nowicki, J. Łuczak, D. Stańczyk, RSC Adv. 2016, 6, 11591.
| Crossref | GoogleScholarGoogle Scholar |
[30] J. Schäffer, M. Alber, W. Korth, M. Cokoja, A. Jess, ChemistrySelect 2017, 2, 11891.
| Crossref | GoogleScholarGoogle Scholar |
[31] A. Cognigni, S. Kampichler, K. Bica, J. Colloid Interface Sci. 2017, 492, 136.
| Crossref | GoogleScholarGoogle Scholar |
[32] M. Taskin, A. Cognigni, R. Zirbs, E. Reimhult, K. Bica, RSC Adv. 2017, 7, 41144.
| Crossref | GoogleScholarGoogle Scholar |
[33] X.-Q. Xiao, G.-X. Jin, J. Organomet. Chem. 2008, 693, 3363.
| Crossref | GoogleScholarGoogle Scholar |
[34] A. R. Parent, R. H. Crabtree, G. W. Brudvig, Chem. Soc. Rev. 2013, 42, 2247.
| Crossref | GoogleScholarGoogle Scholar |
[35] Z. Codolà, J. M. S. Cardoso, B. Royo, M. Costas, J. Lloret-Fillol, Chem. – Eur. J. 2013, 19, 7203.
| Crossref | GoogleScholarGoogle Scholar |
[36] J. M. Koelewijn, M. Lutz, W. I. Dzik, R. J. Detz, J. N. H. Reek, ACS Catal. 2016, 6, 3418.
| Crossref | GoogleScholarGoogle Scholar |
[37] A. Savini, P. Belanzoni, G. Bellachioma, C. Zuccaccia, D. Zuccaccia, A. Macchioni, Green Chem. 2011, 13, 3360.
| Crossref | GoogleScholarGoogle Scholar |
[38] U. Hintermair, S. W. Sheehan, A. R. Parent, D. H. Ess, D. T. Richens, P. H. Vaccaro, G. W. Brudvig, R. H. Crabtree, J. Am. Chem. Soc. 2013, 135, 10837.
| Crossref | GoogleScholarGoogle Scholar |
[39] R. Lalrempuia, N. D. McDaniel, H. Müller-Bunz, S. Bernhard, M. Albrecht, Angew. Chem. Int. Ed. 2010, 49, 9765.
| Crossref | GoogleScholarGoogle Scholar |
[40] P. Bartlett, R. H. Ottewill, J. Chem. Phys. 1992, 96, 3306.
| Crossref | GoogleScholarGoogle Scholar |
[41] J. Łuczak, M. Markiewicz, J. Thöming, J. Hupka, C. Jungnickel, J. Colloid Interface Sci. 2011, 362, 415.
| Crossref | GoogleScholarGoogle Scholar |
[42] D. J. Wasylenko, C. Ganesamoorthy, M. A. Henderson, C. P. Berlinguette, Inorg. Chem. 2011, 50, 3662.
| Crossref | GoogleScholarGoogle Scholar |
[43] B. S. Souza, E. C. Leopoldino, D. W. Tondo, J. Dupont, F. Nome, Langmuir 2012, 28, 833.
| Crossref | GoogleScholarGoogle Scholar |
[44] X. Wang, F. W. Heinemann, M. Yang, B. U. Melcher, M. Fekete, A.-V. Mudring, P. Wasserscheid, K. Meyer, Chem. Commun. 2009, 7405.
| Crossref | GoogleScholarGoogle Scholar |
[45] L. Krause, R. Herbst-Irmer, G. M. Sheldrick, D. Stalke, J. Appl. Cryst. 2015, 48, 3.
| Crossref | GoogleScholarGoogle Scholar |
[46] G. M. Sheldrick, Acta Crystallogr. Sect. A 2015, 71, 3.
| Crossref | GoogleScholarGoogle Scholar |
[47] G. M. Sheldrick, Acta Crystallogr. Sect. C 2015, 71, 3.
| Crossref | GoogleScholarGoogle Scholar |