Abstract
The modern revolution of organic material sciences cannot be justly described if one does not account for the contributions of polymeric materials [1]. Even at this fast pace of development, no other class of materials can match the versatility of macromolecules with regard to their fine-tuneable physical or chemical properties and ease of processing. It is not an exaggeration to claim that any specific functional property of any given polymer would eventually find (if it has not already found) its own importance in the upcoming avenues of science and engineering. In most cases, demand drives discovery of such materials. However, in many cases, mere curiosity drives discovery, broadening the scopes of the applications of various materials. In the case of radical polymers, the story is quite unique, as are the materials [2]. As noted in an earlier chapter, even though the successful synthesis of PTMA was known since 1972 [3], it required three decades for the community to appreciate the vast opportunity of such materials in any viable application. This spark encouraged an entire generation of researchers towards the broader opportunities of radical polymers, and the most significant impact of radical polymers has been in the development of modern approaches towards fully organic energy storage devices [4]. This opportunity is feasible due to the inherent redox-active electronic properties of this class of compounds.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
References
(a) Klawk H (eds) (2006) Organic electronics: materials, manufacturing and applications. Wiley-VCH, Weinheim; (b) Klawk H (eds) (2010) Organic electronics: more materials and applications. Wiley-VCH, Weinheim
Tomlinson EP, Hay ME, Boudouris BW (2014) Radical polymers and their application to organic electronic devices. Macromolecules 47:6145–6158
Kurosaki T, Lee KW, Okawara M (1972) Polymers having stable radicals. I. Synthesis of nitroxyl polymers from 4-methacryloyl derivatives of 2,2,6,6-tetramethylpiperidine. J Polym Sci A 10:3295–3310
Muench S, Wild A, Friebe C, Hȁupler B, Janoschka T, Schubert US (2016) Polymer-based organic batteries. Chem Rev 116:9438–9484
Gracia R, Mecerreyes D (2013) Polymers with redox properties: materials for batteries, biosensors and more. Polym Chem 4:2206–2214
(a) Song Z, Zhou H (2013) Towards sustainable and versatile energy storage devices: an overview of organic electrode materials. Energy Environ Sci 6:2280–2301; (b) Schon TB, McAllister BT, Li P-F, Seferos DS (2016) The rise of organic electrode materials for energy storage. Chem Soc Rev 45:6345–6404
Oyaizu K, Nishide H (2009) Radical polymers for organic electronic devices: a radical departure from conjugated polymers? Adv Mater 21:2339–2344
(a) Nishide H, Oyaizu K (2008) Towards flexible batteries. Science 319:737–738; (b) Janoschka T, Hager M D, Schubert U S (2012) Powering up the future: radical polymers for battery applications. Adv Mater 24:6397–6409
Bobela DC, Hughes BK, Braunecker WA, Kemper TW, Larsen RE, Gennett T (2015) Close packing of nitroxide radicals in stable organic radical polymeric materials. J Phys Chem Lett 6:1414–1419
Nakahara K, Iwasa S, Satoh M, Morioka Y, Iriyama J, Suguro M, Hasegawa E (2002) Rechargeable batteries with organic radical cathodes. Chem Phys Lett 359:351–354
(a) Suga T, Konishi H, Nishide H (2007) Photocrosslinked nitroxide polymer cathode-active materials for application in an organic-based paper battery. Chem Commun 17:1730–1732; (b) Oyaizu K, Ando Y, Konishi H, Nishide H (2008) Nernstian adsorbate-like bulk layer of organic radical polymers for high-density charge storage purposes. J Am Chem Soc 130:14459–14461
(a) Wang Y-H, Hung M-K, Lin C-H, Lin H-C, Lee J-T (2011) Patterned nitroxide polymer brushes for thin-film cathodes in organic radical batteries. Chem Commun 47:1249–1251; (b) Hung M-K, Wang Y-H, Lin C-H, Lin H-C, Lee J-T (2012) Synthesis and electrochemical behaviour of nitroxide polymer brush thin-film electrodes for organic radical batteries. J Mater Chem 22:1570–1577
Beck F, Ruetschi P (2000) Rechargeable batteries with aqueous electrolytes. Electrochem Acta 45:2467–2482
Koshika K, Sano N, Oyaizu K, Nishide H (2009) An ultrafast chargeable organic electrode based on combination of nitroxide radical and aqueous electrolyte. Chem Commun 7:836–838
(a) Chae I S, Koyano M, Oyaizu K, Nishide H (2013) Self-doping inspired zwitterionic pendant design of radical polymers toward a rocking-chair-type organic cathode active material. J Mater Chem A 1:1326–1333; (b) Chae I S, Koyano M, Sukegawa T, Oyaizu K, Nishide H (2013) 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 1:9608–9611
(a) Koshika K, Chikushi N, Sano N, Oyaizu K, Nishide H (2010) A TEMPO-substituted polyacrylamide as a new cathode material: an organic rechargeable device composed of polymer electrodes and aqueous electrolyte. Green Chem 12:1573–1575; (b) Koshika K, Sano N, Oyaizu K, Nishide H (2009) An aqueous, electrolyte-type, rechargeable device utilizing a hydrophilic radical polymer-cathode. Macromol Chem Phys 210:1989–1995; (c) Nakahara K, Oyaizu K, Nishide H (2012) Electrolyte anion-assisted charge transport in a poly(oxoammonium cation/nitroxide radical) redox gels. J Mater Chem 22:13669–13673; (d) Sano N, Tomita W, Hara S, Min C -M, Lee J -S, Oyaizu K, Nishide H (2013) Polyviologen hydrogel with high-rate capability for anodes towards an aqueous electrolyte-type and organic based rechargeable device. ACS Appl Mater Interfaces 5:1355–1361
Alotto P, Guarnieri M, Moro F (2014) Redox flow batteries for the storage of renewable energy: a review. Renew Sust Energ Rev 29:325–335
(a) Soloveichik GL (2015) Flow batteries: current status and trends. Chem Rev 115:11533–11558; (b) Perry ML, Weber AZ (2016) Advanced redox-flow batteries: a perspective. J Electrochem Soc 163:A5064–A5067
Janoschka T, Matin N, Martin U, Friebe C, Morgenstern S, Hiller H, Hager MD, Schubert US (2015) An aqueous, polymer-based redox-flow battery using non-corrosive, safe, and low-cost materials. Nature 527:78–81
(a) Janoschka T, Morgenstern S, Hiller H, Friebe C, Wolkersdorfer K, Haupler B, Hager MD, Schubert US (2015) Synthesis and characterization of TEMPO- and viologen- polymers for water-based redox-flow batteries. Polym Chem 6:7801–7811; (b) Sukegawa T, Masuko I, Oyaizu K, Nishide H (2014) Expanding the dimensionality of polymers populated with organic robust radicals towards flow cell application: Synthesis of TEMPO-crowded bottlebrush polymers using anionic polymerization and ROMP. Macromolecules 47:8611–8617
Winsberg J, Janoschka T, Morgenstern S, Hagemann T, Muench S, Hauffman G, Gohy J-F, Hager MD, Schubert US (2016) Poly(TEMPO)/zinc hybrid-flow battery: a novel, “green,” high voltage and safe energy storage system. Adv Mater 28:2238–2243
Choi W, Ohtani S, Oyaizu K, Nishide H, Geckeler KE (2011) Radical polymer-wrapped SWNTs at a molecular level: high-rate redox mediation through a percolation network for a transparent charge-storage material. Adv Mater 23:4440–4443
Choi W, Endo S, Oyaizu K, Nishide H, Geckeler KE (2013) Robust and efficient charge storage by uniform grafting of TEMPO radical polymer around multi-walled carbon nanotubes. J Mater Chem A 1:2999–3003
Ernould B, Devos M, Bourgeois J-P, Rolland J, Vlad A, Gohy J-F (2015) Grafting of a redox polymer onto carbon nanotubes for high capacity battery materials. J Mater Chem A 3:8832–8839
Aqil A, Vlad A, Piedboeuf M-L, Aqil M, Job N, Melinte S, Detrembleur C, Jerome C (2015) A new design of organic radical batteries (ORBs): carbon nanotube buckypaper electrode functionalized by electrografting. Chem Commun 51:9301–9304
Vlad A, Singh N, Melinte S, Gohy J-F, Ajayan PM (2016) Carbon redox-polymer-gel hybrid supercapacitors. Sci Rep 6:22194. doi:10.1038/srep22194
Kim J-K, Kim Y, Park S, Ko H, Kim Y (2016) Encapsulation of organic active materials in carbon nanotubes for application to high-electrochemical-performance sodium batteries. Energy Environ Sci 9:1264–1269
Guo W, Yin Y-X, Xin S, Guo Y-G, Wan L-J (2012) Superior radical polymer cathode material with a two-electron process redox reaction promoted by graphene. Energy Environ Sci 5:5221–5225
Huang Q, Choi D, Cosimbescu L, Lemmon JP (2013) Multi-electron redox reaction of an organic radical cathode induced by a mesopore carbon network with a nitroxide polymer. Phys Chem Chem Phys 15:20921–20928
Li Y, Jian Z, Lang M, Zhang C, Huang X (2016) Covalently functionalized graphene by radical polymers for graphene-based high-performance cathode materials. ACS Appl Mater Interfaces 8:17352–17359
Suga T, Ohshiro H, Sugita S, Oyaizu K, Nishide H (2009) Emerging n-type redox-active radical polymer for a totally organic polymer-based rechargeable battery. Adv Mater 21:1627–1630
Suga T, Sugita S, Ohshiro H, Oyaizu K, Nishide H (2011) p- and n- type bipolar redox-active radical polymer: toward totally organic polymer-based rechargeable devices with variable configuration. Adv Mater 23:751–754
(a) Hauffman G, Rolland J, Bourgeois J-P, Vlad A, Gohy J -F (2013) Synthesis of nitroxide-containing block copolymers for the formation of organic cathodes. J Polym Sci A 51:101–108; (b) Liedel C, Ober CK (2016) Nanopatterning of stable radical containing block copolymers for highly ordered functional nanomeshes. Macromolecules 49:5884–5892; (c) Hyakutake T, Park JY, Yonekuta Y, Oyaizu K, Nishide H, Advincula R (2010) Nanolithographic patterning via electrochemical oxidation of stable poly(nitroxide radical)s to poly(oxoammonium salt)s. J Mater Chem 20:9616–9618.
Janoschka T, Teichler A, Hȁupler B, Jahnert T, Hager MD, Schubert MD (2013) Reactive inkjet printing of cathodes for organic radical batteries. Adv Mater 3:1025–1028
Author information
Authors and Affiliations
Rights and permissions
Copyright information
© 2017 The Author(s)
About this chapter
Cite this chapter
Mukherjee, S., Boudouris, B.W. (2017). Applications of Radical Polymers in Electrolyte-Supported Devices. In: Organic Radical Polymers. SpringerBriefs in Materials. Springer, Cham. https://doi.org/10.1007/978-3-319-58574-1_3
Download citation
DOI: https://doi.org/10.1007/978-3-319-58574-1_3
Published:
Publisher Name: Springer, Cham
Print ISBN: 978-3-319-58573-4
Online ISBN: 978-3-319-58574-1
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)