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Table 10. The structures and properties of TEMPOs. Introduction of hydrophilic -OH on 4 position improves the solubility of TEMPO in water (2.1 M) due to an increase in polarity. Compound 4-hydroxy-2,2,6,6-tetramethylpiperidin-1-oxyl (4- HO-TEMPO, Entry 2 in Table 10) was explored by Wang et al. as the catholyte material in AORFBs (68). The MV/4-HO-TEMPO battery presented an impressive cycling performance with a capacity retention of 99% over 100 cycles. However, 4-OH-TEMPO displayed relatively high permeability through anion exchange membrane due to the small size of this compound. To suppress the crossover of TEMPO, Liu and Xu et al. explored 4-trimethylammoinium-TEMPO (NMe-TEMPO, Entry 5 in Table 10) (26) and 4-[3-(trimethylammonio)propoxy]-TEMPO (TMAP-TEMPO, Entry 6 in Table 10) (69) in aqueous RFBs. The change of -OH to a bulkier, charged ammonium unit decreased the permeability of TEMPO from 1.34 × 10-9 to 6.40 × 10-10 cm2/s, significantly improved the cycling performance of AORFBs (69). 35 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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