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Figure 4. Chemical Structures of Organic Redox-Active Molecules for RFBs (A) Redox-active molecules with low melting points. (B–E) Redox-active molecules functionalized by ether and ester groups: metal complexes (B), DBBB derivatives (C), NQ derivatives (D), and EPT derivatives (E). (F and G) Fc derivatives (F) and DMFc (G). (H) Schematic representation of the operation of a microporous membrane in a RFB using redox-active oligomers. Reprinted with permission from Hendriks et al.34 Copyright 2018 American Chemical Society. (I) Synthesis and chemical structures of cyclopropenium-based oligomers. Adapted with permission from Hendriks et al.34 Copyright 2018 American Chemical Society. molecules, often suffer from low solubility in nonaqueous electrolytes. Ether and ester groups generally maintain intense interactions with many polar solvents and have been widely used to functionalize many organic redox species such as metal complexes,26 2,5-di-tert-butyl-1,4-bis(2-methoxyethoxy)benzene (DBBB),27 1,4-di- methoxybenzene (DMB),28 benzoquinone (BQ),29 naphthoquinone (NQ),29 and N-ethylphenothiazine (EPT)30 (Figures 4B–4E). On the other hand, it is noted that the incorporation of polar esters and ether functional groups can reduce the crystal- linity of these molecules, leading to liquid redox species with greatly decreased melting points at room temperature.26,27,29,30 A cell based on the liquid NQ deriv- ative without additional solvents demonstrated an energy density of 264 Wh L1, which exceeds most of the reported values.29 Ferrocene (Fc), a representative organometallic redox species, has a low solubility in most organic solvents especially in presence of supporting salts.31,32 Functionalized 1970 Chem 5, 1964–1987, August 8, 2019PDF Image | Development of Redox Flow Batteries Based on New Chemistries
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