Solid-State Polymer Electrolytes Based on AB3-type Miktoarm Star. Copolymers

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1 Supporting Information Solid-State Polymer Electrolytes Based on AB3-type Miktoarm Star Copolymers Daeyeon Lee, Ha Young Jung, and Moon Jeong Park * Department of Chemistry, Pohang University of Science and Technology (POSTECH), Pohang, Korea These authors contributed equally. * Corresponding author (moonpark@postech.ac.kr) 1

2 Experimental Materials: Poly(ethylene glycol) monomethyl ether (PEO, Mn = 2 kg mol -1 ), styrene ( 99%), sodium hydride (NaH, 95%), allyl bromide (99%), potassium tert-butoxide (KOtBu, 99.8%), copper(i) bromide (CuBr, 98%), pentamethyldiethylenetriamine (PMDETA, 99%), trimethylamine (TEA, 99%), α-bromoisobutyryl bromide (BIBB, 98%), tetrahydrofuran (THF, HPLC grade, 99.9%, inhibitor-free), dimethyl sulfoxide (DMSO, 99%), N,Ndimethylformamide (DMF, anhydrous, 99.8%), diethyl ether ( 98.0%), chloroform-d (CDCl3, 99.8 atom% D), dichloromethane (anhydrous, 99.8%), heptane (95%), ethyl acetate ( 99.5%), acetone ( 99.5%), toluene (anhydrous, 99.8%), sodium sulfate (Na2SO4, 99.0%), dithranol ( 90%), lithium bis(trifluoromethane)sulfonimide (LiTFSI, > 99%), and lithium hexafluorophosphate (LiPF6, 98%) were purchased from Sigma-Aldrich. Pentaerythritol tribromide (98%) was purchased from TCI. Molecular Weight Characterization: Matrix-assisted laser desorption/ionization time-offlight (MALDI-TOF, Bruker Autoflex Speed LRF) mass spectrometer in linear mode was employed to determine absolute molecular weights of PEO and allyl (PEO)3. Dithranol in THF was used as matrix solutions. Number average molecular weights of the synthesized block copolymers and miktoarm star copolymers were obtained from 1 H Nuclear Magnetic Resonance ( 1 H NMR, Bruker 300 and 500) spectroscopy by integrating the NMR spectra of PEO and PS in CDCl3, combined with end-group analysis. Molecular weight distributions of the synthesized polymers were characterized by size exclusion chromatography (SEC, Waters Breeze 2 HPLC) using PS standards in THF eluent at a flow rate of 1 ml min -1 (Waters 1515 isocratic HPLC pump), equipped with three PS/DVB columns (Shodex KF-801, KF-802, and KF-803, mm), UV/vis detector (Waters 2489), and refractive index detector (Waters 2414). 2

3 Synthesis of Allyl Pentaerythritol Tribromide: Under argon atmosphere, NaH (1.01 g, 42 mmol) was added to the solution of pentaerythritol tribromide (9.75 g, 25 mmol) and allyl bromide (12.96 ml, 150 mmol) in anhydrous DMF (40 ml) at 0 C. Under stirring, the reactor temperature was slowly returned to room temperature. After 3 h of reaction, the mixtures were dropwise added to saturated NH4Cl (50 ml). The aqueous phases were then extracted twice with diethyl ether and the organic phases were washed five times with distilled water and brine. The obtained mixtures were dried with Na2SO4, followed by filtration and gentle removal of residual solvents by rotary evaporation. The resultant paleyellow oil was further purified by column chromatography (heptane:ethyl acetate = 9:1) to yield 9.70 g of allyl pentaerythritol tribromide in form of a clear oil. 1 H-NMR (300 MHz, CDCl3) δ ppm: 5.93 (m, 1H, -CH=CH2), 5.28 (m, 2H, -CH=CH2), 4.05 (d, 2H, - OCH2CH=CH2), 3.53 (s, 6H, -CCH2Br), 3.46 (s, 2H, -OCH2C-). Synthesis of Allyl (PEO)3: PEO (2 kg mol -1, 15 g, 7.5 mmol) dissolved in anhydrous DMF (60 ml) and NaH (180 mg, 7.5 mmol) was carefully added into the solution under argon atmosphere at 0 C. The reaction mixtures were returned to room temperature and stirred for 2 h. Allyl pentaerythritol tribromide (182.5 mg, 0.5 mmol) was then added into the mixtures, followed by heating to 100 C. After 48 h of reaction under stirring, the reaction mixtures were cooled down to room temperature and distilled water (150 ml) was dropwise added. The aqueous phases were extracted four times with dichloromethane and organic phases were washed twice with brine. Drying with Na2SO4, filtration, rotary evaporation, repeated precipitations in ether, and vacuum drying yielded allyl (PEO)3 mixed with excess unreacted PEO. The undesired PEO was removed by fractionation, as confirmed by MALDI-TOF mass spectrometry. 1 H NMR (300 MHz, CDCl3) δ ppm: 5.93 (m, 1H, -CH=CH2), 5.28 (m, 2H, - CH=CH2), 3.92 (d, 2H, -OCH2CH=CH2), (m, n 4H, -OCH2CH2O-), 3.43 (s, 6H, -CCH2O-), 3.40 (s, 2H, -OCH2C-), 3.38 (s, 9H, -OCH3). 3

4 Synthesis and of Hydroxyl (PEO)3: KOtBu (280.5 mg, 2.5 mmol) was added to allyl (PEO)3 (1.54 g, 0.25 mmol) in DMSO (9 ml) and heated to 100 C under stirring. After 1h of reaction, the mixtures were returned to room temperature and brine (20 ml) was added, followed by extraction of aqueous phases three times with dichloromethane. Organic phases were washed three times with brine and dried with Na2SO4. The resultant products were filtered, dried at reduced pressure, precipitated in ether, and hydrolyzed using HCl (0.1 M) in acetone (10 ml) at 55 C. The final form of hydroxyl (PEO)3 was obtained by repeated extractions using water/dichloromethane, precipitations in ether, and vacuum drying at room temperature. 1 H-NMR (500 MHz, CDCl3) δ ppm: (m, n 4H, -OCH2CH2O- and s, 2H, -OCH2C-), 3.46 (s, 6H, -CCH2O-), 3.38 (s, 9H, -OCH3). Synthesis of (PEO)3-Br Macro-initiator: Mixtures of anhydrous dichloromethane (4.5 ml), TEA (0.1 ml, 0.69 mmol), and hydroxyl (PEO)3 (825 mg, 0.14 mmol) were prepared at room temperature. After cooling the mixtures to 0 C, BIBB (0.14 ml, 1.1 mmol) in dichloromethane (1 ml) was added. The reactor was returned to room temperature and stirred for 24 h. Dichloromethane (40 ml) was added into the reaction mixtures and organic phases were washed three times with distilled water. After drying the organic phases with Na2SO4, the products were recovered by filtration, precipitations in ether, and drying in vacuum. 1 H- NMR (500 MHz, CDCl3) δ ppm: 4.19 (s, 2H, -COOCH2C-), (m, n 4H, - OCH2CH2O-), 3.46 (s, 6H, -CCH2O-), 3.38 (s, 9H, -OCH3), 1.92 (s, 6H, -COOCCH3). Synthesis of PS-(PEO)3 Miktoarm Star Copolymers (S(EO)3): S(EO)3 miktoarm star copolymers were synthesized by atom transfer radical polymerization (ATRP). (PEO)3-Br macro-initiator (0.17 g, mmol), styrene (0.21 g, 2.04 mmol), toluene (0.4 ml) and CuBr (3.87 mg, mmol) were weighed into round-bottom flask and bubbled with argon under stirring. After the addition of PMDETA (9.18 mg, mmol), the mixtures were heated to 80 C and stirred for 12 h. The reaction mixtures were then quickly cooled down to 4

5 room temperature and diluted with toluene. The copper salts were removed by using neutral aluminum oxide and repeated extractions using methylene chloride/water. The complete removal of copper salts was confirmed by elemental analysis. The S(EO)3 miktoarm star copolymers were recovered by repeated precipitations in cold ether, filtration, and vacuum drying. 1 H-NMR (500 MHz, CDCl3) δ ppm: (br, n 5H, -CH2CH(C6H5)), (m, n 4H, -OCH2CH2O- and s, 6H, -CCH2O-), 3.38 (s, 9H, -OCH3), 3.29 (s, 2H, - COOCH2C-), (br, n 3H, -CH2CH(C6H5)), 0.92 (br, 6H, -COOCCH3). Synthesis of PS-PEO Linear Diblock Copolymer (SEO): PEO-Br macro-initiator was synthesized according to the same procedures described for (PEO)3-Br synthesis. SEO block copolymers were synthesized by ATRP. PEO-Br (0.5 g, mmol), styrene (0.88 g, 8.47 mmol), toluene (1.5 ml) and CuBr (11.62 mg, mmol) were weighted into roundbottom flask. The reaction mixtures were bubbled with argon under stirring. After adding PMDETA (27.73 mg, mmol) into the mixtures, the reaction was proceeded at 80 C for 12 h under stirring. The reaction mixtures were then quickly cooled down to room temperature and the reaction was terminated by diluting the mixtures with toluene. After removing copper salts, the products were precipitated in cold ether, filtered, and vacuumdried to yield SEO block copolymers. PEO-Br: 1 H-NMR (500 MHz, CDCl3) δ ppm: 4.35 (t, 2H, -COOCH2C-), (m, n 4H, -OCH2CH2O-), 3.40 (s, 3H, -OCH3), 1.97 (s, 6H, - COOCCH3). SEO: 1 H-NMR (500 MHz, CDCl3) δ ppm: (br, n 5H, - CH2CH(C6H5)), (m, n 4H, -OCH2CH2O-), 3.38 (s, 3H, -OCH3), (br, n 3H, -CH2CH(C6H5)), 0.92 (br, 6H, -COOCCH3). Doping of Polymers with Lithium Salts: Predetermined quantities of LiTFSI (or LiPF6) and synthesized polymers were dissolved in methanol/benzene (20/80 vol%) mixtures to prepare ca. 5 wt% solutions. Polymer membranes were prepared by solvent casting inside argon-filled 5

6 glove box with moisture and oxygen levels less than 0.1 ppm, followed by vacuum drying at 60 C for a week. The dimension of solvent-cast membrane was 1 cm 1 cm 200 μm. Small-Angle X-ray Scattering (SAXS) Experiments: Self-assembled morphologies of SEO diblock copolymers and S(EO)3 miktoarm star copolymers with and without lithium saltdoping were investigated by synchrotron SAXS experiments using the PLS-II 4C beamline at the Pohang Accelerator Laboratory. The 4C beamline provided temperature-controlled sample stage and two-dimensional detector to users. The wavelength (λ) of the incident X-ray beam was Å (Δλ/λ = 10-4 ). Samples were loaded in an airtight sample cell inside an argon-filled glove box to avoid water contamination of hygroscopic samples. Differential Scanning Calorimetry (DSC) Experiments: DSC thermograms of SEO and S(EO)3 copolymers with and without lithium salt-doping were acquired using a TA Instruments (model Q20) mg of samples were loaded into aluminum pan inside an argon-filled glovebox and an empty pan was used as a reference. The heat of melting and melting transition temperature were monitored at a fixed heating/cooling rate of 10 C/min. Ionic Conductivity Measurements: In an argon-filled glovebox, through-plane conductivities of lithium salt-doped SEO and S(EO)3 samples were measured by impedance spectroscopy using VersaSTAT 3 (Princeton Applied Research). Two-electrode cell was prepared for the measurements, which consists of stainless steel blocking electrodes and Pt working/counter electrodes. Samples were annealed for 30 min at each temperature and data were collected in a wide frequency range of Hz. Transmission Electron Microscopy (TEM) Experiments: Cross-sectional TEM images of SEO and S(EO)3 electrolytes doped with LiTFSI at r = 0.06 were obtained a Zeiss LIBRA 200FE microscope operating at 200 kv. The samples were solvent-cast onto formvar-coated grids inside argon-filled glove box, followed by thermal annealing at 120 C for 48 h. The PEO phases were darkened by ruthenium tetroxide (RuO4) staining for 20 min. 6

7 Rheology: The dynamic storage moduli (G ) and loss moduli (G ) of SEO and S(EO)3 copolymers were measured by employing Anton Paar MCR 302 (Graz, Austria) rheometer, equipped with a parallel plate (8 mm diameter) under nitrogen atmosphere. All measurements were performed at a 0.5 mm gap with a small strain of 0.1%. Frequency sweeps were performed in the range of rad/s at different temperatures. For rheology measurements, LiPF6 was employed as a lithium salt considering hygroscopic nature of LiTFSI so as to avoid water contamination during sample loading into the rheometer. 7

8 Supporting Table Table S1. Materials Used in the Present Study Polymer M n a (g/mol) M w /M n b PS c d-spacing (nm) d PEO-Br SEO (5-6) SEO (8-6) allyl (PEO) hydroxyl (PEO) PEO 3 -Br S(EO) 3 (5-6) S(EO) 3 (8-6) a number average molecular weight, measured by combining MALDI-TOF Mass and 1 H-NMR. b measured by SEC in THF using PS standards. c calculated using densities of PS (1.07 g cm -3 ) and PEO (1.21 g cm -3 ). d at r = 0.06, measured by SAXS. 8

9 Table S2. Heat of Melting ( H m ), Melting Transition Temperature (T m ), and Degree of Crystallinity (X c ) of S(EO) 3 and SEO electrolytes, Determined by DSC Experiments. S(EO) 3 (5-6) S(EO) 3 (8-6) r = 0 r = 0.02 r = 0.06 r = 0 r = 0.02 r = 0.06 Hm (J/g) Tm ( C) a b X c SEO (5-6) SEO (8-6) r = 0 r = 0.02 r = 0.06 r = 0 r = 0.02 r = 0.06 Hm (J/g) Tm ( C) a b X c a determined during the second heating at 10 C/min. b X c = H m / (w PEO 215.6) based on H m = J/g of 100% crystalline PEO and w PEO (weight fraction of PEO in copolymer). 9

10 Supporting Figures Figure S1. (a) MALDI-TOF mass spectrum and (b) 1 H NMR spectrum (in CDCl3) of allyl (PEO)3. Characteristic 1 H NMR peaks are marked in (b). 10

11 Figure S2. 1 H NMR spectrum (in CDCl3) and peak assignments of hydroxyl (PEO)3. 11

12 Figure S3. 1 H NMR spectrum (in CDCl3) and peak assignments of (PEO)3-Br macro-initiator. 12

13 Figure S4. 1 H NMR spectrum (in CDCl3) and peak assignments of SEO (5-6) block copolymer. 13

14 Figure S5. (a) DSC thermograms of S(EO)3 (8-6) and SEO (8-6) doped with LiTFSI (r = 0.06) at heating/cooling rates of 10 C/min. (b) The DSC thermograms obtained during second heating at 10 C/min, displaying dissimilar Tg values of (PEO)3 and PEO phases at r =

15 Figure S6. DSC thermograms of S(EO)3 (8-6), S(EO)3 (5-6), SEO (8-6), and SEO (5-6) doped with LiTFSI (r = 0.06) obtained during second heating at 10 C/min, displaying dissimilar Tg values of PEO phases for S(EO)3 and SEO electrolytes. 15

16 Figure S7. SAXS profiles of S(EO)3 (5-6) miktoarm star copolymer and SEO (5-6) diblock copolymer doped with LiTFSI (r = 0.06). 16

17 Figure S8. Storage (G, filled symbols) and loss (G, open symbols) moduli of S(EO)3 (8-6) and SEO (8-6) doped with LiPF6 (r = 0.06) during frequency sweep at a strain of 0.1%, measured at (a) 50 C and (b) 60 C. 17

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