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Gels 2022, 8, 193 4 of 13 The driving forces for the self-assembly of B8 were investigated (Figure 1b,c): The fourier transform infrared (FT-IR) spectrum of the B8 xerogel revealed that O-H and N- H stretching vibration bands overlap at 3400 cm−1, CH2 stretching vibration bands are observed at 2911 and 2840 cm–1, and the characteristic carbonyl stretching vibration band appeared at 1631 cm−1. Nevertheless, the corresponding stretching vibration bands of B8 in a DMF solution were blue-shifted, indicative of the participation of the O-H, N-H, and C=O groups in hydrogen bonding, as well as the presence of van der Waals (VDW) forces between the side chains of B8 [33]. 1H NMR spectral analysis of B8 at variable concentrations in DMSO-d6 was also conducted in the presence of BMPTFSI. At 5% (w/v) B8, the N-H signal of the amide group was observed at 7.470 ppm, N-H signals of the urea group were observed at 5.699 ppm, and different O-H signals were observed at 4.718 and 4.451 ppm. However, with the increase in the B8 concentration, all the above-mentioned signals shifted downfield, indicating that the protons of amide, urea, and hydroxyl groups are involved in hydrogen-bond formation [34]. X-ray diffraction (XRD) patterns of the B8-BMPTFSI ionogel (Figure 1d) were recorded to obtain information regarding the self-assembly of B8. Three clear reflection peaks corresponding to d-spacings of 29.57 Å, 14.51 Å, and 9.87 Å in a ratio of 1: 1/2: 1/3 were observed, respectively, suggesting the presence of a lamellar structure with a periodicity of 29.57 Å in the gel state [35]. The peak corresponding to a d-spacing of 3.56 Å is characteristic of the π-π stacking distance, indicative of the presence of π-π interactions between B8 molecules [36]. The peak with a d-spacing of 4.02 and 4.50 Å corresponded to the hydrogen- bonding distance of A8 molecules and the packing distance between the long alkyl chains of A8 molecules, respectively [37]. Attempts were made to prepare a B8 crystal to investigate the self-assembly mode of B8; however, all attempts were futile. Fortunately, however, the crystal of Z1, a precursor compound of G16 and A8, was obtained from an H2O/methanol (1:1) solution, and its single-crystal XRD data were collected (Figure S2, Table S1, and CIF S1): Assemblies of D-gluconic acetal fragments along the 1D direction were observed. Based on the single- crystal XRD data of Z1 and by theoretical calculation (Gaussian 09), the self-assembly mode of B8 was optimized and simulated (CIF S2). Figure 1e, f shows the calculated assembly mode of B8: The H-bonding interactions of polyhydroxy fragments and π···π interactions of chlorinated benzenes undoubtedly played a key role in the formation of the 1D assembly [27,37], and the two chlorine atoms on the benzene ring played a subtle role in supramolecular assemblies, which is well known to involve dispersive halogen interactions (halogen–arene and halogen–halogen interactions) [38,39]. In addition, H- bonding interactions of C=O···H-N between side chains were observed, which were also responsible for the 1D assembly of B8 (Figure 1f), the bond lengths of which were 3.983 Å, corresponding to a d-spacing of 4.02 Å in the XRD experiment (Figure 1d) [40]. C –Cl···H-N interactions (Figure 1e) [37,41] and VDW forces between side chains played a key role in the 3D assembly of B8. As shown in Figure 1e and f, the distance between side chains, the width of 1D assembly, the distance of the layered structure, and the distance of B8 molecule were 4.683 Å, 10.019 Å, 14.578 Å, and 29.843 Å, respectively, corresponding to d-spacings of 4.50 Å, 9.87 Å, 14.51 Å, and 29.57 Å in the XRD spectrum (Figure 1d). Although slight deviations were observed, it was sufficient to confirm the reliability of our calculation results. In conclusion, the 1D self-assembly of B8 gelators depended on π-π stacking between benzene rings, hydrogen-bonding between polyol fragments, and C=O···H-N H-bonding interactions between side chains. The C-Cl···H-N interactions and VDW forces between side chains were responsible for the 3D self-assembly of B8 assemblies. In addition, the re-contact and re-assembly of the functional groups on the 1D assembly surface after mechanical damage is the essence of thixotropy [42,43].PDF Image | Thixotropic Ionogel Electrolyte for Sodium Batteries
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