[en] We report on the synthesis of a new polymer ionic liquid (PIL) based on polyvinylimidazolium bearing a pendent nitroxide radical on each monomer unit. Firstly, the quaternization of 1 vinylimidazole by a brominated alkoxyamine, i.e. a protected tetramethylpiperidinyloxy (TEMPO) nitroxide, was achieved. Then, the bromide anion was substituted by anion exchange reaction for the bis(trifluoro-methanesulfonyl)imide (TFSI) anion. The as-obtained monomer was successfully polymerized by free radical polymerization at low temperature (40 °C) by using 2,2′-azobis(4 methoxy-2.4-dimethyl valeronitrile) as initiator. Finally, the CO bond of the alkoxyamine pendant groups was thermally cleaved releasing the redox-active TEMPO nitroxide radicals. The PIL bearing TEMPO groups was coated onto a carbon nanotubes buckypaper and tested as cathode in a lithium ion battery. Such battery remarkably exhibits a high charge/discharge rate capability, e.g. at 60C the full charge is reached in 1 min and a high cycling stability; 100% of the initial capacity 60 mA h/g is kept after 1300 cycles.
Research center :
CESAM - Complex and Entangled Systems from Atoms to Materials - ULiège Center for Education and Research on Macromolecules (CERM)
Disciplines :
Materials science & engineering Chemistry
Author, co-author :
Aqil, Mohamed ; University of Liège (ULiège), Complex and Entangled Systems from Atoms to Materials (CESAM), Center for Education and Research on Macromolecules (CERM) > University of Mohammed Premier, Oujda, Morocco
Ouhib, Farid ; University of Liège (ULiège), Complex and Entangled Systems from Atoms to Materials (CESAM), Center for Education and Research on Macromolecules (CERM)
Aqil, Abdelhafid ; University of Liège (ULiège), Complex and Entangled Systems from Atoms to Materials (CESAM), Center for Education and Research on Macromolecules (CERM)
El Idrissi, Abdelrahman; University of Mohammed Premier, Oujda, Morocco
Detrembleur, Christophe ; University of Liège (ULiège), Complex and Entangled Systems from Atoms to Materials (CESAM), Center for Education and Research on Macromolecules (CERM)
Jérôme, Christine ; University of Liège (ULiège), Complex and Entangled Systems from Atoms to Materials (CESAM), Center for Education and Research on Macromolecules (CERM)
Language :
English
Title :
Polymer ionic liquid bearing radicals as an active material for organic batteries with ultrafast charge-discharge rate
Publication date :
September 2018
Journal title :
European Polymer Journal
ISSN :
0014-3057
eISSN :
1873-1945
Publisher :
Elsevier Ltd
Volume :
106
Pages :
242-248
Peer reviewed :
Peer Reviewed verified by ORBi
Name of the research project :
The Walloon Region in the frame of the "Batflex" project
Funders :
BELSPO - Service Public Fédéral de Programmation Politique scientifique [BE] F.R.S.-FNRS - Fonds de la Recherche Scientifique [BE] Walloon region [BE]
Nakahara, K., Iriyama, J., Iwasa, S., Suguro, M., Satoh, M., Cairns, E.J., Al-laminated film packaged organic radical battery for high-power applications. J. Power Sources 163 (2007), 1110–1113, 10.1016/j.jpowsour.2006.10.003.
Suga, T., Ohshiro, H., Ugita, S., Oyaizu, K., Nishide, H., Emerging n-type redox-active radical polymer for a totally organic polymer-based rechargeable battery. Adv. Mater. 21 (2009), 1627–1630, 10.1002/adma.200803073.
Janoschka, T., Hager, M.D., Schubert, U.S., Powering up the future: radical polymers for battery applications. Adv. Mater. 24 (2012), 6397–6409, 10.1002/adma.201203119.
Chae, I.S., Koyano, M., Sukegawa, T., Oyaizu, K., Nishide, H., Redox equilibrium of a zwitterionic radical polymer in a non-aqueous electrolyte as a novel Li+ host material in a Li-ion battery. J. Mater. Chem. A, 1, 2013, 9608, 10.1039/c3ta12076g.
Sukegawa, T., Kai, A., Oyaizu, K., Nishide, H., Synthesis of pendant nitronyl nitroxide radical-containing poly(norbornene)s as ambipolar electrode-active materials. Macromolecules 46 (2013), 1361–1367, 10.1021/ma302278h.
Bugnon, L., Morton, C.J.H., Novak, P., Vetter, J., Nesvadba, P., Synthesis of poly(4-methyacryloyloxy-TEMPO) via group-transfer polymerization and its evaluation in organic radical battery. Chem. Mater. 19 (2007), 2910–2914, 10.1021/cm063052h.
Hyakutake, T., Park, J.Y., Yonekuta, Y., Oyaizu, K., Nishide, H., Advincula, R., Nanolithographic patterning via electrochemical oxidation of stable poly(nitroxide radical)s to poly(oxoammonium salt)s. J. Mater. Chem., 20, 2010, 9616, 10.1039/c0jm02241a.
Lebègue, E., Brousse, T., Gaubicher, J., Retoux, R., Cougnon, C., Toward fully organic rechargeable charge storage devices based on carbon electrodes grafted with redox molecules. J. Mater. Chem. A, 2, 2014, 8599, 10.1039/c4ta00853g.
Huang, Q., Choi, D., Cosimbescu, L., Lemmon, J.P., Multi-electron redox reaction of an organic radical cathode induced by a mesopore carbon network with nitroxide polymers. Phys. Chem. Chem. Phys., 15, 2013, 20921, 10.1039/c3cp54358g.
Kim, J.K., Cheruvally, G., Ahn, J.H., Seo, Y.G., Choi, D.S., Lee, S.H., Song, C.E., Organic radical battery with PTMA cathode: effect of PTMA content on electrochemical properties. J. Ind. Eng. Chem. 14 (2008), 371–376, 10.1016/j.jiec.2007.12.002.
Nakahara, K., Iriyama, J., Iwasa, S., Suguro, M., Satoh, M., Cairns, E.J., Cell properties for modified PTMA cathodes of organic radical batteries. J. Power Sources 165 (2007), 398–402, 10.1016/j.jpowsour.2006.11.044.
Guo, W., Yin, Y.-X., Xin, S., Guo, Y.-G., Wan, L.-J., Superior radical polymer cathode material with a two-electron process redox reaction promoted by graphene. Energy Environ. Sci. 5 (2012), 5221–5225, 10.1039/C1EE02148F.
Zhang, K., Hu, Y., Wang, L., Monteiro, M.J., Jia, Z., Pyrene-functionalized PTMA by NRC for greater π–π stacking with rGO and enhanced electrochemical properties. ACS Appl. Mater. Interf. 9 (2017), 34900–34908, 10.1021/acsami.7b09604.
Li, Y., Jian, Z., Lang, M., Zhang, C., Huang, X., Covalently functionalized graphene by radical polymers for graphene-based high-performance cathode materials. ACS Appl. Mater. Interf. 8 (2016), 17352–17359, 10.1021/acsami.6b05271.
Choi, W., Ohtani, S., Oyaizu, K., Nishide, H., Geckeler, K.E., Radical polymer-wrapped SWNTs at a molecular level: High-rate redox mediation through a percolation network for a transparent charge-storage material. Adv. Mater. 23 (2011), 4440–4443, 10.1002/adma.201102372.
Kim, J.-K., Scheers, J., Ahn, J.-H., Johansson, P., Matic, A., Jacobsson, P., Nano-fibrous polymer films for organic rechargeable batteries. J. Mater. Chem. A. 1 (2013), 2426–2430, 10.1039/C2TA00743F.
Oyaizu, K., Tatsuhira, H., Nishide, H., Facile charge transport and storage by a TEMPO-populated redox mediating polymer integrated with polyaniline as electrical conducting path. Polym. J. 47 (2015), 212–219, 10.1038/pj.2014.124.
Aqil, A., Vlad, A., Piedboeuf, M.-L., Aqil, M., Job, N., Melinte, S., Detrembleur, C., Jérôme, C., A new design of organic radical batteries (ORBs): carbon nanotube buckypaper electrode functionalized by electrografting. Chem. Commun. 51 (2015), 9301–9304, 10.1039/C5CC02420J.
Komaba, S., Tanaka, T., Ozeki, T., Taki, T., Watanabe, H., Tachikawa, H., Fast redox of composite electrode of nitroxide radical polymer and carbon with polyacrylate binder. J. Power Sources 195 (2010), 6212–6217, 10.1016/j.jpowsour.2009.10.078.
Lee, S.H., Kim, J.-K., Cheruvally, G., Choi, J.-W., Ahn, J.-H., Chauhan, G.S., Song, C.E., Electrochemical properties of new organic radical materials for lithium secondary batteries. J. Power Sources 184 (2008), 503–507, 10.1016/j.jpowsour.2008.04.003.
Kim, J.-K., Matic, A., Ahn, J.-H., Jacobsson, P., Song, C.-E., Preparation and application of TEMPO-based di-radical organic electrode with ionic liquid-based polymer electrolyte. RSC Adv., 2, 2012, 10394, 10.1039/c2ra20795h.
Dai, Y., Zhang, Y., Gao, L., Xu, G., Xie, J., Electrochemical performance of organic radical cathode with ionic liquid based electrolyte. J. Electrochem. Soc. 158 (2011), A291–A295, 10.1149/1.3533360.
MacFarlane, D.R., Tachikawa, N., Forsyth, M., Pringle, J.M., Howlett, P.C., Elliott, G.D., Davis, J.H., Watanabe, M., Simon, P., Angell, C.A., Energy applications of ionic liquids. Energy Environ. Sci. 7 (2014), 232–250, 10.1039/C3EE42099J.
Chen, X.J., Xu, D., Qiu, L.H., Li, S.C., Zhang, W., Yan, F., Imidazolium functionalized TEMPO/iodide hybrid redox couple for highly efficient dye-sensitized solar cells. J. Mater. Chem. A 1 (2013), 8759–8765, 10.1039/C3ta11521f.
Li, C.T., Lee, C.P., Lee, C.T., Li, S.R., Sun, S.S., Ho, K.C., Iodide-free ionic liquid with dual redox couples for dye-sensitized solar cells with high open-circuit voltage. ChemSusChem 8 (2015), 1244–1253, 10.1002/cssc.201403204.
Hernández, G., Işik, M., Mantione, D., Pendashteh, A., Navalpotro, P., Shanmukaraj, D., Marcilla, R., Mecerreyes, D., Redox-active poly(ionic liquid)s as active materials for energy storage applications. J. Mater. Chem. A 5 (2017), 16231–16240, 10.1039/C6TA10056B.
Aqil, M., Aqil, A., Ouhib, F., El Idrissi, A., Detrembleur, C., Jérôme, C., RAFT polymerization of an alkoxyamine bearing acrylate, towards a well-defined redox active polyacrylate. RSC Adv. 5 (2015), 85035–85038, 10.1039/C5RA16839B.
M. Aqil, A. Aqil, F. Ouahib, C. Detrembleur, C. Jerome, A. El Idrissi, A novel synthetic route toward a PTA as active materials for organic radical batteries, in: 2016 Int. Renew. Sustain. Energy Conf., IEEE, 2016, pp. 961–965. 10.1109/IRSEC.2016.7984033.
Mecerreyes, D., Polymeric ionic liquids: broadening the properties and applications of polyelectrolytes. Prog. Polym. Sci. 36 (2011), 1629–1648, 10.1016/J.PROGPOLYMSCI.2011.05.007.
Yuan, J., Mecerreyes, D., Antonietti, M., Poly(ionic liquid)s: an update. Prog. Polym. Sci. 38 (2013), 1009–1036, 10.1016/J.PROGPOLYMSCI.2013.04.002.
Tebben, L., Studer, A., Nitroxides: applications in synthesis and in polymer chemistry. Angew. Chem. – Int. Ed. 50 (2011), 5034–5068, 10.1002/anie.201002547.
Wang, F., Rong, M.Z., Zhang, M.Q., Reversibility of solid state radical reactions in thermally remendable polymers with C-ON bonds. J. Mater. Chem., 22, 2012, 13076, 10.1039/c2jm30578j.
Wang, J., Chu, H., Li, Y., Why single-walled carbon nanotubes can be dispersed in imidazolium-based ionic liquids. ACS Nano 2 (2008), 2540–2546, 10.1021/nn800510g.
Tunckol, M., Durand, J., Serp, P., Carbon nanomaterial-ionic liquid hybrids. Carbon N. Y. 50 (2012), 4303–4334, 10.1016/j.carbon.2012.05.017.
