High-Power-Density Organic Radical Batteries

Springer Science and Business Media LLC - Tập 375 - Trang 1-35 - 2017
Christian Friebe1,2, Ulrich S. Schubert1,2
1Laboratory of Organic and Macromolecular Chemistry (IOMC), Friedrich Schiller University Jena, Jena, Germany
2Center for Energy and Environmental Chemistry Jena (CEEC Jena), Friedrich Schiller University Jena, Jena, Germany

Tóm tắt

Batteries that are based on organic radical compounds possess superior charging times and discharging power capability in comparison to established electrochemical energy-storage technologies. They do not rely on metals and, hence, feature a favorable environmental impact. They furthermore offer the possibility of roll-to-roll processing through the use of different printing techniques, which enables the cost-efficient fabrication of mechanically flexible devices. In this review, organic radical batteries are presented with the focus on the hitherto developed materials and the key properties thereof, e.g., voltage, capacity, and cycle life. Furthermore, basic information, such as significant characteristics, housing approaches, and applied additives, are presented and discussed in the context of organic radical batteries.

Tài liệu tham khảo

Andersson BA, Råde I (2001) Metal resource constraints for electric-vehicle batteries. Transp Res Part D Transp Environ 6:297 Gandini A, Lacerda TM (2015) From monomers to polymers from renewable resources: recent advances. Prog Polym Sci 48:1 Nishide H, Oyaizu K (2008) Toward flexible batteries. Science 319:737 Nishide H, Suga T (2005) Organic radical battery. Electrochem Soc Interface 14:32 Satoh M (2005) Organic radical battery and its technology. NEC J Adv Technol 2:262 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 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 Song Z, Zhou H (2013) Towards sustainable and versatile energy storage devices: an overview of organic electrode materials. Energy Environ Sci 6:2280 Muench S, Wild A, Friebe C, Häupler B, Janoschka T, Schubert US (2016) Polymer-based organic batteries. Chem Rev 116:9438 Kumaresan K, Guo Q, Ramadass P, White RE (2006) Cycle life performance of lithium-ion pouch cells. J Power Sources 158:679 Friebe C, Schubert US (2015) Development of active organic and polymeric materials for batteries and solar cells: introduction to essential characterization techniques. Adv Energy Mater 5:1500858 Linden D, Reddy TB (2002) Handbook of Batteries. McGraw-Hill, New York Nakahara K, Iwasa S, Iriyama J, Morioka Y, Suguro M, Satoh M, Cairns EJ (2006) Electrochemical and spectroscopic measurements for stable nitroxyl radicals. Electrochim Acta 52:921 Janoschka T, Teichler A, Häupler B, Jähnert T, Hager MD, Schubert US (2013) Reactive inkjet printing of cathodes for organic radical batteries. Adv Energy Mater 3:1025 Nakahara K, Oyaizu K, Nishide H (2011) Organic radical battery approaching practical use. Chem Lett 40:222 Kemper TW, Larsen RE, Gennett T (2014) Relationship between molecular structure and electron transfer in a polymeric nitroxyl-radical energy storage material. J Phys Chem C 118:17213 Oyaizu K, Nishide H (2009) Radical polymers for organic electronic devices: a radical departure from conjugated polymers? Adv Mater 21:2339 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 Satoh M, Nakahara K, Iriyama J, Iwasa S, Suguro M (2004) High power organic radical battery for information systems. IEICE Trans Electron 87:2076 Suga T, Pu Y-J, Oyaizu K, Nishide H (2004) Electron-transfer kinetics of nitroxide radicals as an electrode-active material. Bull Chem Soc Jpn 77:2203 Rostro L, Wong SH, Boudouris BW (2014) Solid state electrical conductivity of radical polymers as a function of pendant group oxidation state. Macromolecules 47:3713 Nakahara K, Iriyama J, Iwasa S, Suguro M, Satoh M, Cairns EJ (2007) Cell properties for modified PTMA cathodes of organic radical batteries. J Power Sources 165:398 Nakahara K, Iriyama J, Iwasa S, Suguro M, Satoh M, Cairns EJ (2007) High-rate capable organic radical cathodes for lithium rechargeable batteries. J Power Sources 165:870 Katsumata T, Satoh M, Wada J, Shiotsuki M, Sanda F, Masuda T (2006) Polyacetylene and polynorbornene derivatives carrying TEMPO. Synthesis and properties as organic radical battery materials. Macromol Rapid Commun 27:1206 Sukegawa T, Sato K, Oyaizu K, Nishide H (2015) Efficient charge transport of a radical polyether/SWCNT composite electrode for an organic radical battery with high charge-storage density. RSC Adv 5:15448 Hauffman G, Maguin Q, Bourgeois J-P, Vlad A, Gohy J-F (2014) Micellar cathodes from self-assembled nitroxide-containing block copolymers in battery electrolytes. Macromol Rapid Commun 35:228 Chae IS, 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 Yoshihara S, Isozumi H, Kasai M, Yonehara H, Ando Y, Oyaizu K, Nishide H (2010) Improving charge/discharge properties of radical polymer electrodes influenced strongly by current collector/carbon fiber interface. J Phys Chem B 114:8335 Lin C-H, Lee J-T, Yang D-R, Chen H-W, Wu S-T (2015) Nitroxide radical polymer/carbon-nanotube-array electrodes with improved C-rate performance in organic radical batteries. RSC Adv 5:33044 Vlad A, Rolland J, Hauffman G, Ernould B, Gohy J-F (2015) Melt-polymerization of TEMPO methacrylates with nano carbons enables superior battery materials. Chem Sus Chem 8:1692 Vlad A, Singh N, Melinte S, Gohy J-F, Ajayan PM (2016) Carbon redox-polymer-gel hybrid super capacitors. Sci Rep 6:22194 Vlad A, Singh N, Rolland J, Melinte S, Ajayan PM, Gohy J-F (2014) Hybrid supercapacitor-battery materials for fast electrochemical charge storage. Sci Rep 4:4315 Du ZZ, Ai W, Xie LH, Huang W (2014) Organic radical functionalized graphene as a superior anode material for lithium-ion batteries. J Mater Chem A 2:9164 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 nitroxide polymers. Phys Chem Chem Phys 15:20921 Guo W, Su J, Li Y-H, Wan L-J, Guo Y-G (2012) Nitroxide radical polymer/graphene nanocomposite as an improved cathode material for rechargeable lithium batteries. Electrochim Acta 72:81 Nakahara K, Iriyama J, Iwasa S, Suguro M, Satoh M, Cairns EJ (2007) Al-laminated film packaged organic radical battery for high-power applications. J Power Sources 163:1110 Chae IS, 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 Kim J-K, Scheers J, Ahn J-H, Johansson P, Matic A, Jacobsson P (2013) Nano-fibrous polymer films for organic rechargeable batteries. J Mater Chem A 1:2426 Kim J-K (2013) Micro-fibrous organic radical electrode to improve the electrochemical properties of organic rechargeable batteries. J Power Sources 242:683 Liu CM, Chen J, Wang FQ, Yi BL (2012) Improvement of electrochemical properties of PTMA cathode by using carbon blacks with high specific surface area. Russ J Electrochem 48:1052 Bugnon L, Morton CJH, Novak P, Vetter J, Nesvadba P (2007) Synthesis of poly(4-methacryloyloxy-TEMPO) via group-transfer polymerization and its evaluation in organic radical battery. Chem Mater 19:2910 Nishide H, Iwasa S, Pu Y-J, Suga T, Nakahara K, Satoh M (2004) Organic radical battery: nitroxide polymers as a cathode-active material. Electrochim Acta 50:827 Kim J-K, Cheruvally G, Choi J-W, Ahn J-H, Choi DS, Song CE (2007) Rechargeable organic radical battery with electrospun, fibrous membrane-based polymer electrolyte. J Electrochem Soc 154:A839 Deng L-F, Li X-H, Xiao L-X, Zhang Y-H (2003) Synthesis and electrochemical properties of polyradical cathode material for lithium second batteries. J Cent South Univ Tech 10:190 Kim J-K, Cheruvally G, Choi J-W, Ahn J-H, Lee SH, Choi DS, Song CE (2007) Effect of radical polymer cathode thickness on the electrochemical performance of organic radical battery. Solid State Ion 178:1546 Kim J-K, Cheruvally G, Ahn J-H, Seo Y-G, Choi DS, Lee S-H, Song CE (2008) Organic radical battery with PTMA cathode: effect of PTMA content on electrochemical properties. J Ind Eng Chem 14:371 Kim J-K, Ahn J-H, Cheruvally G, Chauhan GS, Choi J-W, Kim D-S, Ahn H-J, Lee SH, Song CE (2009) Electrochemical properties of rechargeable organic radical battery with PTMA cathode. Metal Mater Int 15:77 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 Kim Y, Jo C, Lee J, Lee CW, Yoon S (2012) An ordered nanocomposite of organic radical polymer and mesocellular carbon foam as cathode material in lithium ion batteries. J Mater Chem 22:1453 Lin H-C, Li C-C, Lee J-T (2011) Nitroxide polymer brushes grafted onto silica nanoparticles as cathodes for organic radical batteries. J Power Sources 196:8098 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 Lin C-H, Chou W-J, Lee J-T (2012) Three-dimensionally ordered macroporous nitroxide polymer brush electrodes prepared by surface-initiated atom transfer polymerization for organic radical batteries. Macromol Rapid Commun 33:107 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 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 Takahashi K, Korolev K, Tsuji K, Oyaizu K, Nishide H, Bryuzgin E, Navrotskiy A, Novakov I (2015) Facile grafting-onto-preparation of block copolymers of TEMPO and glycidyl methacrylates on an oxide substrate as an electrode-active layer. Polymer 68:310 Suga T, Konishi H, Nishide H (2007) Photocrosslinked nitroxide polymer cathode-active materials for application in an organic-based paper battery. Chem Commun 1370 Katsumata T, Qu J, Shiotsuki M, Satoh M, Wada J, Igarashi J, Mizoguchi K, Masuda T (2008) Synthesis, characterization, and charge/discharge properties of polynorbornenes carrying 2,2,6,6-tetramethylpiperidine-1-oxy radicals at high density. Macromolecules 41:1175 Dai Y, Zhang Y, Gao L, Xu G, Xie J (2011) Electrochemical performance of organic radical cathode with ionic liquid based electrolyte. J Electrochem Soc 158:A291 Qu JQ, Katsumata T, Satoh M, Wada J, Masuda T (2009) Poly (7-oxanorbornenes) carrying 2,2,6,6-tetramethylpiperidine-1-oxy(TEMPO) radicals: synthesis and charge/discharge properties. Polymer 50:391 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 Suguro M, Iwasa S, Kusachi Y, Morioka Y, Nakahara K (2007) Cationic polymerization of poly(vinyl ether) bearing a TEMPO radical: a new cathode-active material for organic radical batteries. Macromol Rapid Commun 28:1929 Suguro M, Iwasa S, Nakahara K (2008) Fabrication of a practical and polymer-rich organic radical polymer electrode and its rate dependence. Macromol Rapid Commun 29:1635 Koshika K, Sano N, Oyaizu K, Nishide H (2009) An ultrafast chargeable polymer electrode based on the combination of nitroxide radical and aqueous electrolyte. Chem Commun 836 Sertkol SB, Sinirlioglu D, Esat B, Muftuoglu AE (2015) A novel cathode material based on polystyrene with pendant TEMPO moieties obtained via click reaction and its use in rechargeable batteries. J Polym Res 22:136 Suga T, Yoshimura K, Nishide H (2006) Nitroxide-substituted polyether as a new material for batteries. Macromol Symp 245–246:416 Qu J, Katsumata T, Satoh M, Wada J, Igarashi J, Mizoguchi K, Masuda T (2007) Synthesis and charge/discharge properties of polyacetylenes carrying 2,2,6,6-tetramethyl-1-piperidinoxy radicals. Chem Eur J 13:7965 Qu JQ, Fujii T, Katsumata T, Suzuki Y, Shiotsuki M, Sanda F, Satoh M, Wada J, Masuda T (2007) Helical polyacetylenes carrying 2,2,6,6-tetramethyl-1-piperidinyloxy and 2,2,5,5-tetramethyl-1-pyrrolidinyloxy moieties: their synthesis, properties, and function. J Polym Sci A Polym Chem 45:5431 Qu JQ, Khan FZ, Satoh M, Wada J, Hayashi H, Mizoguchi K, Masuda T (2008) Synthesis and charge/discharge properties of cellulose derivatives carrying free radicals. Polymer 49:1490 Qu J, Morita R, Satoh M, Wada J, Terakura F, Mizoguchi K, Ogata N, Masuda T (2008) Synthesis and properties of DNA complexes containing 2,2,6,6-tetramethyl-1-piperidinoxy(TEMPO) moieties as organic radical battery materials. Chem Eur J 14:3250 Zhang XH, Li HQ, Li LT, Lu GL, Zhang S, Gu LN, Xia YY, Huang XY (2008) Polyallene with pendant nitroxyl radicals. Polymer 49:3393 Ibe T, Frings RB, Lachowicz A, Kyo S, Nishide H (2010) Nitroxide polymer networks formed by Michael addition: on site-cured electrode-active organic coating. Chem Commun 46:3475 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 Aydın M, Esat B, Kılıç Ç, Köse ME, Ata A, Yılmaz F (2011) A polythiophene derivative bearing TEMPO as a cathode material for rechargeable batteries. Eur Polym J 47:2283 Aydin M, Esat B (2015) A polythiophene derivative bearing two electroactive groups per monomer as a cathode material for rechargeable batteries. J Solid State Electrochem 19:2275 Xu LH, Yang F, Su C, Ji LL, Zhang C (2014) Synthesis and properties of novel TEMPO-contained polypyrrole derivatives as the cathode material of organic radical battery. Electrochim Acta 130:148 Lee SH, Kim J-K, Cheruvally G, Choi J-W, Ahn J-H, Chauhan GS, Song CE (2008) Electrochemical properties of new organic radical materials for lithium secondary batteries. J Power Sources 184:503 Xu LH, Ji LL, Wang GS, Zhang C, Su C (2016) A novel nitroxide radical polymer-containing conductive polyaniline as molecular skeleton: its synthesis and electrochemical properties as organic cathode. Ionics 22:1377 Suguro M, Mori A, Iwasa S, Nakahara K, Nakano K (2009) Syntheses and electrochemical properties of TEMPO radical substituted silicones: active material for organic radical batteries. Macromol Chem Phys 210:1402 Lebègue E, Brousse T, Gaubicher J, Retoux R, Cougnon C (2014) Toward fully organic rechargeable charge storage devices based on carbon electrodes grafted with redox molecules. J Mater Chem A 2:8599 Jähnert T, Janoschka T, Hager MD, Schubert US (2014) Polymers with n-type nitroxide side groups: synthesis and electrochemical characterization. Eur Polym J 61:105 Aricò AS, Bruce P, Scrosati B, Tarascon J-M, van Schalkwijk W (2005) Nanostructured materials for advanced energy conversion and storage devices. Nat Mater 4:366 Tarascon J-M, Armand M (2001) Issues and challenges facing rechargeable lithium batteries. Nature 414:359 Oyaizu K, Kawamoto T, Suga T, Nishide H (2010) Synthesis and charge transport properties of redox-active nitroxide polyethers with large site density. Macromolecules 43:10382 Nesvadba P, Bugnon L, Maire P, Novák P (2010) Synthesis of a novel spirobisnitroxide polymer and its evaluation in an organic radical battery. Chem Mater 22:783 Suga T, Pu Y-J, Kasatori S, Nishide H (2007) Cathode- and anode-active poly (nitroxylstyrene)s for rechargeable batteries: p- and n-type redox switching via substituent effects. Macromolecules 40:3167 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 Jähnert T, Hager MD, Schubert US (2014) Application of phenolic radicals for antioxidants, as active materials in batteries, magnetic materials and ligands for metal-complexes. J Mater Chem A 2:15234 Jähnert T, Häupler B, Janoschka T, Hager MD, Schubert US (2014) Polymers based on stable phenoxyl radicals for the use in organic radical batteries. Macromol Rapid Commun 35:882 Morita Y, Nishida S, Murata T, Moriguchi M, Ueda A, Satoh M, Arifuku K, Sato K, Takui T (2011) Organic tailored batteries materials using stable open-shell molecules with degenerate frontier orbitals. Nat Mater 10:947 Lipunova GN, Fedorchenko TG, Chupakhin ON (2013) Verdazyls: synthesis, properties, application. Russ Chem Rev 82:701 Gilroy JB, McKinnon SDJ, Koivisto BD, Hicks RG (2007) Electrochemical studies of verdazyl radicals. Org Lett 9:4837 Morgan IS, Peuronen A, Hänninen MM, Reed RW, Clérac R, Tuononen HM (2014) 1-Phenyl-3-(pyrid-2-yl)benzo[e][1, 2, 4]triazinyl: the first “Blatter Radical” for coordination chemistry. Inorg Chem 53:33 Berezin AA, Zissimou G, Constantinides CP, Beldjoudi Y, Rawson JM, Koutentis PA (2014) Route to benzo- and pyrido-fused 1,2,4-triazinyl radicals via N′-(het)aryl-N′-[2-nitro(het)aryl]hydrazides. J Org Chem 79:314 Constantinides CP, Koutentis PA, Krassos H, Rawson JM, Tasiopoulos AJ (2011) Characterization and magnetic properties of a “super stable” radical 1,3-diphenyl-7-trifluoromethyl-1,4-dihydro-1,2,4-benzotriazin-4-yl. J Org Chem 76:2798 Blatter HM, Lukaszewski H (1968) A new stable free radical. Tetrahedron Lett 9:2701 Miura Y, Muranaka Y (2006) Electrochemical study of stable N-alkoxyarylaminyl radicals. Electrochim Acta 52:1053 Miura Y, Momoki M, Fuchikami T, Teki Y, Itoh K, Mizutani H (1996) Exceptionally persistent nitrogen-centered free radicals. Syntheses, ESR spectra, isolation, and X-ray crystallographic structures of N-(arylthio)-2-tert-butyl-4,6-diarylphenylaminyl and N-(arylthio)-4-tert-butyl-2,6-diarylphenylaminyl radicals. J Org Chem 61:4300 Miura Y, Tanaka A (1992) Cyclic voltammetric behaviour of exceptionally persistent nitrogen-centred free radicals. N-(arylthio)-2,4,6-triphenylanilino radicals. Electrochim Acta 37:2095 Oyaizu K, Suga T, Yoshimura K, Nishide H (2008) Synthesis and characterization of radical-bearing polyethers as an electrode-active material for organic secondary batteries. Macromolecules 41:6646 Qu J, Katsumata T, Satoh M, Wada J, Masuda T (2007) Synthesis and properties of polyacetylene and polynorbornene derivatives carrying 2,2,5,5-tetramethyl-1-pyrrolidinyloxy moieties. Macromolecules 40:3136 Sukegawa T, Kai A, Oyaizu K, Nishide H (2013) Synthesis of pendant nitronyl nitroxide radical-containing poly (norbornene)s as ambipolar electrode-active materials. Macromolecules 46:1361 Koizumi T, Ohfuji H, Tanaka S, Shigematsu S, Akutagawa N, Satoh M, Miura Y (2014) Charge-discharge behavior of secondary organic radical battery using 2-aryl nitronyl nitroxides as the cathode active material. Chem Lett 43:1092 Li F, Zhang YP, Kwon SR, Lutkenhaus JL (2016) Electropolymerized polythiophenes bearing pendant nitroxide radicals. ACS Macro Lett 5:337 Kunz TK, Wolf MO (2011) Electrodeposition and properties of TEMPO functionalized polythiophene thin films. Polym Chem 2:640 Takahashi Y, Hayashi N, Oyaizu K, Honda K, Nishide H (2008) Totally organic polymer-based electrochromic cell using TEMPO-substituted polynorbornene as a counter electrode-active material. Polym J 40:763 Ruff I, Friedrich VJ (1971) Transfer diffusion. I. Theoretical. J Phys Chem 75:3297 Dahms H (1968) Electronic conduction in aqueous solution. J Phys Chem 72:362 Donnet J-B (1994) Fifty years of research and progress on carbon black. Carbon 32:1305 Bourrat X (1993) Electrically conductive grades of carbon black: structure and properties. Carbon 31:287 Liang C, Li Z, Dai S (2008) Mesoporous carbon materials: synthesis and modification. Angew Chem Int Ed 47:3696 Choi Y-K, K-i Sugimoto, Song S-M, Gotoh Y, Ohkoshi Y, Endo M (2005) Mechanical and physical properties of epoxy composites reinforced by vapor grown carbon nanofibers. Carbon 43:2199 Endo M, Kim YA, Hayashi T, Nishimura K, Matusita T, Miyashita K, Dresselhaus MS (2001) Vapor-grown carbon fibers (VGCFs): basic properties and their battery applications. Carbon 39:1287 Balandin AA, Ghosh S, Bao W, Calizo I, Teweldebrhan D, Miao F, Lau CN (2008) Superior thermal conductivity of single-layer graphene. Nano Lett 8:902 Stoller MD, Park S, Zhu Y, An J, Ruoff RS (2008) Graphene-based ultracapacitors. Nano Lett 8:3498 Geim AK, Novoselov KS (2007) The rise of graphene. Nat Mater 6:183 Cao L, Sadaf S, Beladi-Mousavi SM, Walder L (2013) PolyTEMPO and polyviologen on carbon nanotubes: syntheses, structures and organic battery applications. Eur Polym J 49:1923 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 Hecht DS, Hu L, Irvin G (2011) Emerging transparent electrodes based on thin films of carbon nanotubes, graphene, and metallic nanostructures. Adv Mater 23:1482 Chou S-L, Pan Y, Wang J-Z, Liu H-K, Dou S-X (2014) Small things make a big difference: binder effects on the performance of Li and Na batteries. Phys Chem Chem Phys 16:20347 Xu W, Read A, Koech PK, Hu D, Wang C, Xiao J, Padmaperuma AB, Graff GL, Liu J, Zhang J-G (2012) Factors affecting the battery performance of anthraquinone-based organic cathode materials. J Mater Chem 22:4032 Komaba S, Tanaka T, Ozeki T, Taki T, Watanabe H, Tachikawa H (2010) Fast redox of composite electrode of nitroxide radical polymer and carbon with polyacrylate binder. J Power Sources 195:6212 Xu K (2004) Nonaqueous liquid electrolytes for lithium-based rechargeable batteries. Chem Rev 104:4303 Aurbach D, Daroux ML, Faguy PW, Yeager E (1987) Identification of surface films formed on lithium in propylene carbonate solutions. J Electrochem Soc 134:1611 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 toward an aqueous electrolyte-type and organic-based rechargeable device. ACS Appl Mater Interfaces 5:1355 Jähnert T, Häupler B, Janoschka T, Hager MD, Schubert US (2013) Synthesis and charge-discharge studies of poly (ethynylphenyl) galvinoxyles and their use in organic radical batteries with aqueous electrolytes. Macromol Chem Phys 214:2616 Janoschka T, Hager MD, Schubert US (2012) Powering up the future: radical polymers for battery applications. Adv Mater 24:6397 Wild A, Strumpf M, Häupler B, Hager MD, Schubert US (2016) All-organic battery composed of thianthrene- and TCAQ-based polymers. Adv Energy Mater 1601415