Opportunities and Challenges for Organic Electrodes in Electrochemical Energy Storage.
TL;DR: This review provides a comprehensive overview of all reported cell configurations that involve electroactive organic compounds working either in the solid state or in solution for aqueous or nonaqueous electrolytes and highlights the most promising systems based on such various chemistries.
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Abstract: As the world moves toward electromobility and a concomitant decarbonization of its electrical supply, modern society is also entering a so-called fourth industrial revolution marked by a boom of electronic devices and digital technologies. Consequently, battery demand has exploded along with the need for ores and metals to fabricate them. Starting from such a critical analysis and integrating robust structural data, this review aims at pointing out there is room to promote organic-based electrochemical energy storage. Combined with recycling solutions, redox-active organic species could decrease the pressure on inorganic compounds and offer valid options in terms of environmental footprint and possible disruptive chemistries to meet the energy storage needs of both today and tomorrow. We review state-of-the-art developments in organic batteries, current challenges, and prospects, and we discuss the fundamental principles that govern the reversible chemistry of organic structures. We provide a comprehensive overview of all reported cell configurations that involve electroactive organic compounds working either in the solid state or in solution for aqueous or nonaqueous electrolytes. These configurations include alkali (Li/Na/K) and multivalent (Mg, Zn)-based electrolytes for conventional "sealed" batteries and redox-flow systems. We also highlight the most promising systems based on such various chemistries relying on appropriate metrics such as operation voltage, specific capacity, specific energy, or cycle life to assess the performances of electrodes.
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Figures
Figure 1. Forecast of the world’s energy needs up to 2050. With the changing lifestyles of an increasing number of inhabitants, our energy rate demand will double from 14 TW (2010) to 28 TW (2050). TOE = ton of oil equivalent. Reproduced with permission from ref 112. Copyright 2015 Nature Publishing Group. 
Table 7. continued 
Figure 11. Voltage profiles of selected high-capacity OEMs measured vs Li including (A) poly(S-r-DIB) (reproduced with permission from ref 266. Copyright 2013 Nature Publishing group), (B) S-PAN (reproduced with permission from ref 268. Copyright 2015 American Chemical Society), (C) Li2C6O6 (reproduced with permission from ref 82. Copyright 2008 John Wiley & Sons, Inc.), (D) C6O6 (reproduced with permission from ref 269. Copyright 2019 John Wiley & Sons, Inc.), (E) DMBQ (reproduced with permission from ref 270. Copyright 2010 Elsevier Ltd.), (F) P5Q (reproduced with permission from ref 273. Copyright 2014 American Chemical Society), (G) poly-LiDHAQS (reproduced with permission from ref 276. Copyright 2017 John Wiley & Sons, Inc.), (H) PTO (reproduced from ref 257. Copyright 2013 The Royal Society of Chemistry), and (I) 3Q (reproduced with permission from ref 277. Copyright 2013 Nature Publishing group). 
Figure 16. Voltage profiles of selected OEMs studied measured vs Mg (A−E) and Al (F). (A) Carbyne polysulfide (reproduced from ref 373), (B) PHBQS (reproduced with permission from ref 371. Copyright 2016 Elsevier Ltd.), (C) DMBQ (reproduced with permission from ref 370. Copyright 2016 The Electrochemical Society), (D) P14AQ (reproduced with permission from ref 366. Copyright 2018 Elsevier Ltd.), (E) P(NDI2OD-T2) P14AQ (reproduced with permission from ref 366. Copyright 2018 Elsevier Ltd.), and (F) PQ-Δ (reproduced with permission from ref 380. Copyright 2016 Nature Publishing Group). 
Figure 23. (a) Cycling performance and rate capability reported by Wang and co-workers of the cell with 0.25 M 15D3GAQ as posolyte and lithium foil as anode (reproduced with permission from ref 447. Copyright 2012 The Royal Society of Chemistry). (b) Cycling performance of the Li/MPT flow cell reported by Lu and co-workers (reproduced with permission from ref 450. Copyright 2018 American Chemical Society). (c) Cycling performances of ORFBs based on MePh/DBMMB 0.3 M in DME− M LiTFSI (left) or BzNSN/DBMMB 0.5 M in ACN 1 M LiTFSI (right) reported by Wei and co-workers (reproduced with permission from refs 452 and 453. Copyright 2016 and 2017 American Chemical Society). (d) Symmetric flow cell characterization of MEEPT 0.5 M in ACN 0.5 M TEABF4 reported by Milshtein and co-workers (reproduced with permission from ref 454. Copyright 2016 The Royal Society of Chemistry). Constant current cycling at 100 mA cm−2 (left), capacity vs cycle number at different current densities (right). (e) Molecule used by Sisto and co-workers to develop dialysis membrane-based ORFBs (left) together with the cycling performance (right), reproduced from ref 455. 
Figure 8. General architecture of an electrochemical cell for energy storage whatever the considered technology is. Note that additional electrolyte can be stored externally and then pumped through the cell in the particular case of a flow battery (see Section 9). (a) Cell under discharge (namely galvanic cell) at 100% depth-of-discharge (DOD). (b) Cell under charge (namely electrolysis cell) at 100% state-of-charge (SOC); the electromotive force value (emf = EI=0) is, in principle, at the maximum value. The measured capacity, Q (in mAh), is experimentally obtained by integrating the operating time with current: ∫= · = ·ΔQ I t dt I t( )t
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A systematic study of the co-solvent effect for an all-organic redox flow battery
TL;DR: In this paper, the authors used 1,4-di-tert-butyl-2,5-dimethoxybenzene as the anode and cathode active species in an all-organic redox-flow battery.
Improved electro-grafting of nitropyrene onto onion-like carbon via in situ electrochemical reduction and polymerization: Tailoring redox energy density of the supercapacitor positive electrode
Bihag Anothumakkool,Yuman Sayed-Ahmad-Baraza,Christopher P. Ewels,Pierre-Louis Taberna,Barbara Daffos,Patruce Simon,Thierry Brousse,Joël Gaubicher +7 more
TL;DR: In this article, an improved method for the physical grafting of 1-nitropyrene (Pyr-NO2) onto highly graphitized carbon onion is reported, which is achieved through a lowering of the onset potential of the pyrene polymerization via in situ reduction of the NO2 group.
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The Graphite Intercalation Compounds and their Applications
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TL;DR: In this paper, the strength of the in-plane bonds allows the planes to remain coherent and the lamellar structure of graphite is characterized by a heterodesmic behavior, which leads the plane to be easily separable under mechanical or chemical interactions.
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A classification of organic redox reactions and writing balanced equations for them, with special attention to heteroatoms and heterocyclic compounds
TL;DR: In this article, the authors classified organic redox reactions as atom transfers (balanced by inspection) or as more complex transformations, which are balanced by change in oxidation number, ON, or change in DOX value.
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