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Gels 2022, 8, 193 9 of 13 isocyanate was purchased from Shanghai Macklin Biochemical Co., Ltd. BMPTFSI was purchased from Lanzhou Greenchem ILS, LIPC, and CAS (Lanzhou, China). The chemical reagents were commercially available and directly utilized without further purification. 4.2. Synthesis A8: Synthetic route of B8 is shown in Figure S1. Precursor B6 was synthesized according to the method reported previously [52]. First, 3.9 g (8.72 mmol) of B6 was dissolved in 40 mL of anhydrous DMSO at room temperature and then cooled to 0 ◦C followed by the dropwise addition of 2 mL (11.34 mmol) of octyl isocyanate. Then, the reaction mixture was warmed to room temperature and stirred vigorously for 2 h, followed by pouring it into 200 mL of distilled water under vigorous stirring. A large amount of a white solid precipitated, which was collected by filtration. The filter cake was three times washed with distilled water. After drying, B8 was obtained as a white powder. Yield: 4.24 g (6.98 mmol, 80%). 4.3. Chemical Characterization 2, 4-(3, 4-dichloro) Benzylidene-N-(6- (3-octylureido) hexyl)-D-gluconamide (B8) 1H NMR (400 MHz, DMSO-d6, 25 ◦C): δ7.89 (d, 1H), 7.67 (d, 1H), 7.55 (dd, J = 8.9, 1.4Hz, 1H), 7.47 (t, J = 6.1Hz, 1H), 5.68−5.74 (m, 2H), 5.67 (s, 1H), 4.73 (t, J = 7.4Hz, 2H), 4.46 (t, J = 5.8Hz, 1H), 4.35 (d, 1H), 4.00 (d, 1H), 3.76 (dd, J = 8.9, 1.3Hz, 1H), 3.60−3.67 (m, 1H), 3.52−3.58 (m, 1H), 3.38−3.45 (m, 1H), 3.06−3.15 (m, 2H), 2.89−2.97 (m, 4H), 1.28−1.46 (m, 4H), 1.23 (s, 16H), 0.85 (t, J = 6.8Hz, 3H). 13C NMR (100 MHz, C2D6O, 25 ◦C): δ169.2, 159.6, 138.2, 132.6, 131.8, 129.9, 128.8, 126.4, 99.1, 80.6, 79.3, 69.2, 62.8, 62.4, 39.7, 39.4, 38.6, 31.7, 30.2, 29.9, 29.2, 29.1, 26.7, 26.1, 22.4, 13.3. HRMS (ESI): m/z calcd. for C28H45Cl2N3O7Na+ [M + Na] + 628.2527, found 628.2526. Mp: 179−180 ◦C. All the spectra of B8 are shown in Figure S6–S8. 4.4. Instrumentation Gelation tests were investigated by the typical tube-inversion method. The pre- weighed gelator in a certain solvent in a sealed test tube (inner diameter: 13 mm) was heated until its dissolution, then the resultant solution was cooled to room temperature. The test tube was inverted, and gelation was confirmed when a homogeneous substance was formed with no gravitational flow. The heating temperature selected to dissolve a certain gelator must be less than its melting point to prevent compound deterioration. The CGC is defined as the minimum amount of a gelator required to immobilize 1 mL of solvent. The Tg was determined by the “falling ball method” described previously [27]. The xerogel was prepared by freeze-drying following solvent exchange [28]; the ionogel was immersed into water for 5 days, and the water was refreshed every 5 h; solvent exchange was conducted at room temperature without stirring and ultrasonication, etc.; and the xerogel was obtained by subsequent freeze-drying step. The following experiments and tests were conducted at room temperature and a humidity of 50% unless specified otherwise. Rheological studies of ionogels were conducted using a rheometer (Anton Paar Physica MCR 301) equipped with a plate (15 mm diameter). The gels were equilibrated at 25 ◦C between the plates that were adjusted to a gap of 0.5 mm. The frequency sweep at a constant strain of 0.05% was obtained from 0.1 to 100 rad/s. Strain sweep was performed in the 0.01−150% range at a constant frequency (1 Hz). Time sweep was conducted to observe the recovery property of the gel. First, a constant strain of 0.05% was applied on the sample. Then, a constant strain that was sufficient to break the gel was applied, followed by the application of a constant strain (0.05%) again. The storage modulus G’ and the loss modulus G” of the sample were recorded as functions of time in this experiment. All NMR spectra were recorded on a Bruker DPX 400 MHz spectrometer. Mass spectra were recorded on a TOF-QII high-resolution mass spectrometer. Morphologies of the thin gel samples on a glass plate were investigated by polarizing optical microscopy (POM,PDF Image | Thixotropic Ionogel Electrolyte for Sodium Batteries
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