New Class of Single-Ion-Conducting Solid Polymer Electrolytes Derived from Polyphenols
Source abstract
Abstract
New polyphenols containing ether substituents have been prepared by enzymatic polymerization of the corresponding phenol monomers. The polyphenols were reacted with lithium hydroxide to obtain lithium polyphenolates (LPF-1 and LPF-2) which have been characterized as a new class of lithium ion sources for rechargeable lithium batteries. A number of solid polymer electrolytes were prepared by mixing these salts with a high molecular weight poly(ethylene oxide). High ionic conductivities were observed for the electrolytes derived from lithiated polyphenol containing pendant triethylene glycol monomethyl ether groups.
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OpenAlex topics: Advanced Battery Materials and Technologies · Advancements in Battery Materials · Advanced Battery Technologies Research
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References (35)
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24. Synthesis of Monomer1.In a 500-mL single-neck round-bottomed flask fitted with a mechanical stirrer, were placed hydroquinone (30.88 g, 279.71 mmol), OEG-OTs13(88.96 g, 279.75 mmol), KOH (46.97 g, 837.11 mmol) and 200 mL of DMSO. The mixture was stirred overnight at room temperature (water bath), and then transferred to a separatory funnel using 50 mL of water. The solution was extracted 3× with diethyl ether (100, 50, and 50 mL) to remove both unreacted tosylate and disubstituted byproduct. The solution was then acidified with 50 mL of concentrated HCl and extracted 3× with chloroform (100, 50, and 50 mL); the combined organic layers were washed twice with 100 mL of water, dried over MgSO4, and concentrated in vacuo. The product, which contained traces of sludge, was further purified by filtering through a column (alumina) with ethyl acetate: methanol (95:5) as eluent. Yield: 38.5 g (54%, straw colored liquid). FT-IR (neat): 3333, 2877, 1663, 1511, 1453, 1354, 1234, 1103, 945, 830, 756 cm-1.1H NMR (CDCl3, 300 MHz) δ: 6.72−6.83 (m, 4H), 4.02 (t, 2H), 3.81 (t, 2H), 3.73−3.66 (m, 6H), 3.58 (t, 2H), 3.38 (s, 3H), 2.65 (s, 1H) ppm.13C NMR (CDCl3, 300 MHz) δ: 151.8, 150.4, 115.7, 115.3, 71.5, 70.2, 70.1, 69.5, 67.6, 58.6, 39.9 ppm. Anal. Calcd for C13H20O5: C, 60.94; H, 7.81. Found: C, 60.83; H, 7.90.
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33. Synthesis of PF-1. In a 250-mL single-neck round-bottomed flask fitted with a mechanical stirrer, 8.31 g (34.46 mmol) of monomer1, dissolved in 25 mL of dioxane, was added to an ice cold (5 °C) solution of 24 mg of HRP-II in 55 mL of HEPES buffer. To the mixture was added 5 mL of 30% hydrogen peroxide solution in five portions (1 mL, 10-min interval). With stirring, the solution was allowed to come to room temperature and then stirred overnight. Dioxane was removed under reduced pressure on a rotovap, and the highly viscous polymer was separated from the aqueous phase. The aqueous phase was decanted off, and the contents of the flask were washed with water (3×) and isopentane (2×), and the residue dried at 50 °C under high vacuum to give 7.1 g (86%) of1as a deep red waxy solid. FT-IR (neat): 3318, 2876, 1674, 1510, 1454, 1387, 1353, 1285, 1234, 1108, 1067, 948, 830, 756 cm-1.1H NMR (CDCl3, 300 MHz) δ: 6.82 (s, 1H), 6.75 (s, 1H), 4.05 (m, 2H), 3.79 (m, 2H), 3.75−3.57 (m, 6H), 3.53 (t, 2H), 3.36 (s, 3H), 2.40 (s, 1H) ppm.13C NMR (CDCl3, 300 MHz) δ: 152.7, 151.8, 150.7, 115.7, 115.3, 71.6, 70.2, 69.5, 67.8, 58.7 ppm. Anal. Calcd for C13H18O5: C, 61.42; H, 7.07. Found: C, 61.27; H, 6.85. Synthesis ofPF-2. ThePF-2was prepared fromp-methoxyphenol by following the aforementioned procedure, to give a light brown solid in 90% yield.
34. Lithiation of Polyphenols.Lithiation of polyphenols (PF-1orPF-2) was performed by dissolving the polymer (4 g) in 20 mL of dioxane, followed by addition of a solution of LiOH (1 equiv with respect to the repeat unit) in 10 mL of water. The solution was stirred for 30 min and evaporated to dryness on a rotovap. Final drying was performed at high vacuum at 60 °C. The lithiated polymer salts (LPF-1andLPF-2) were obtained as dry dark red powders. The salts were hygroscopic and stored in a glovebox. FT-IR ofLPF-1(KBr): 2878, 1673, 1510, 1456, 1388, 1353, 1284, 1232, 1109, 1067, 946, 831, 755 cm-1.
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