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Scheme 1. Proposed demonstration mechanisms for 2,6-DBEAQ. Functionalization of the quinone framework with -SO3H increased the solubility of quinones in sulfuric acid (62). Aziz and Gordon et al. utilized sulfonic acid-substituted AQs in acidic AORFBs (47, 63). Under acidic conditions, the RFB using -SO3H substituted AQs and bromine afforded working potentials ranging from 0.8 V to 1.1 V. The AORFBs with 1 M AQs (corresponding to 2 M electrons) delivered an energy density comparable to commercial VRBs. Both alkaline and acidic electrolytes are highly corrosive. It is essential to develop advanced AORFBs under pH-neutral conditions. Liu et al. and Aziz et al. designed and synthesized two different types of AQs with enhanced solubility in pH-neutral aqueous media (64, 65). The ammonium sulfonate-substituted AQs (AQDS(NH4)2, Entry 19 in Table 2) showed substantially improved solubility compared to the sodium sulfonate-substituted AQs due to the hydrophilic property of NH4+ and hydrogen bonds formed among NH4+ cation and carbonyl on AQ backbone (Figure 4) (64). Aziz et al. synthesized PEG-modified AQs (PEGAQ) (65) with a maximum concentration of 2.24 M for neat PEGAQ (Entry 20 in Table 2), giving a maximal volumetric capacity of 120.1 Ah/L. Figure 4. Schematic hydrogen bonding interactions proposed for AQDS(NH4)2. Reproduced with permission from reference (64). Copyright 2019 Wiley. Quinones can also be applied in non-aqueous RFBs (29, 66). Different from the redox processes in aqueous electrolytes, quinones in non-aqueous electrolytes displayed two one-electron redox reactions. Compound 1,4-bismethoxyethoxy anthraquinone (BMEAQ, Entry 24 in Table 2) exhibited a high solubility in acetonitrile (MeCN) (0.47 M) and presented two redox potential at −1.33 and −1.89 V vs. Ag/Ag+, respectively. Unfortunately, the reduced AQ radical anions (AQ– and AQ2–) were reactive toward electron-deficient groups, such as MeCN or tetrafluoroborate 13 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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