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Aza-aromatic compounds show good performance in AORFBs; however, they are only soluble in strong alkaline electrolyte. Molecular engineering to incorporate polar units would increase the solubility in pH-neutral aqueous electrolytes. Imide Phthalimide is an imide derivative of phthalic anhydride. The hydrogen on the N position can be readily replaced with functional groups. Phthalimides can undergo one-electron reduction to form radical anions (Scheme 6). The commercially available N-methylphthalimide (MePh, Entry 1 in Table 6) delivered a redox potential of –1.79 V vs. Ag/Ag+ in LiTFSI- dimethoxyethane (DME) (84). However, the phthalimide radical anions were susceptible to carbonate, MeCN, and BF4–. Molecular modification of MePh with -NR3+ groups increases the solubility and stability at the same time. Sanford et al. explored N-(trimethylammonio)butylphthalimide (Entry 2 in Table 6) in an all- organic non-aqueous RFB (51). Paired with cyclopropenium salts, the obtained battery displayed an excellent cycling performance with a potential of 3.2 V. Scheme 6. Structure and redox reaction of phthalimides. In addition, N-butylphthalimide (Entry 3 in Table 6) delivered an enhanced reversibility and high concentration in eutectic-based anolytes (85). Yu et al. proposed that a 6-fold increase in solubility can be achieved in a mix of electrolytes of N-butylphthalimide, urea, and LiTFSI. The introduction of urea decreased the viscosity of electrolytes and improved the reversibility of phthalimide radical anions. In addition to the phthalimide, Jin et al. developed two copolymers, namely naphthalene- 1,4,5,8-tetracarboxylic acid dianhydride-ethylene diamine copolymer (PI1, Entry 4 in Table 6) and naphthalene-1,4,5,8-tetracarboxylic acid dianhydride-p-phenylenediamine copolymer (PI2, Entry 5 in Table 6), and applied them particulate slurry in aqueous RFBs (Scheme 7) (86). Uniformly dispersed polymer particulate suspensions overcome the solubility limitation. In addition, the micro- sized polymer particulate suspensions can be coupled with cheap commercial dialysis membranes. This work provided new insights and inspirations for exploiting novel insoluble anolyte materials in advanced energy storage systems. Moreover, Wang and coworkers introduced ammonium to naphthalene diimide to improve its solubility in aqueous electrolytes (Entry 6 in Table 6) (87). The ammonium-functionalized naphthalene diimide displayed a solubility of 0.68 M in water and two redox peaks in aqueous electrolytes, making naphthalene diimide a promising candidate for AORFBs. Imide derivatives display low solubility in non-aqueous electrolytes and is almost insoluble in aqueous electrolytes. Although they can be used in slurry batteries, the utilization of polymers in slurry batteries are at the expense of energy capacity. It is necessary to develop high-soluble imide derivatives by molecular engineering. 24 Qin and Fan; Clean Energy Materials ACS Symposium Series; American Chemical Society: Washington, DC, 2020.PDF Image | Electroactive Materials Next-Generation Redox Flow Batteries
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