Hydrogen-Bonded, Hierarchically Structured Single-Component Chiral Poly(ionic liquid) Porous Membranes: Facile Fabrication and Application in Enantioselective Separation

Open AccessCCS ChemistryCOMMUNICATION5 Sep 2022Hydrogen-Bonded, Hierarchically Structured Single-Component Chiral Poly(ionic liquid) Porous Membranes: Facile Fabrication and Application in Enantioselective Separation Binmin Wang, Lei Wang, Zhengtai Zha, Yingyi Hu, Luyao Xu and Hong Wang Binmin Wang Key Laboratory of Functional Polymer Materials, Ministry of Education, Institute of Polymer Chemistry, College of Chemistry, Nankai University, Tianjin 300071 Google Scholar More articles by this author , Lei Wang Key Laboratory of Functional Polymer Materials, Ministry of Education, Institute of Polymer Chemistry, College of Chemistry, Nankai University, Tianjin 300071 School of Materials Science and Engineering, Shaanxi University of Science and Technology, Xi’an 710021 Google Scholar More articles by this author , Zhengtai Zha Key Laboratory of Functional Polymer Materials, Ministry of Education, Institute of Polymer Chemistry, College of Chemistry, Nankai University, Tianjin 300071 Google Scholar More articles by this author , Yingyi Hu Key Laboratory of Functional Polymer Materials, Ministry of Education, Institute of Polymer Chemistry, College of Chemistry, Nankai University, Tianjin 300071 Google Scholar More articles by this author , Luyao Xu Key Laboratory of Functional Polymer Materials, Ministry of Education, Institute of Polymer Chemistry, College of Chemistry, Nankai University, Tianjin 300071 Google Scholar More articles by this author and Hong Wang *Corresponding author: E-mail Address: [email protected] Key Laboratory of Functional Polymer Materials, Ministry of Education, Institute of Polymer Chemistry, College of Chemistry, Nankai University, Tianjin 300071 Google Scholar More articles by this author https://doi.org/10.31635/ccschem.021.202101543 SectionsSupplemental MaterialAboutAbstractPDF ToolsAdd to favoritesDownload CitationsTrack Citations ShareFacebookTwitterLinked InEmail The development of strategies for producing well-defined chiral porous membranes for the rapid and efficient enantioseparation of racemic mixtures remains a great challenge. Herein, we introduce an innovative, simple, and easily scalable synthetic strategy to manufacture chiral porous polymer membranes (CPPMs) bearing chiral NH groups by crosslinking single-component chiral poly(ionic liquid)s (PILs) with water molecules via hydrogen (H)-bonding. The chiral evolution process from ionic liquid monomers to PILs to chiral porous membrane has been well-demonstrated by a suite of experimental results from single-crystal structural analysis, 1H NMR spectra, circular dichroism spectrum, and in situ scanning confocal microscopy. We demonstrate that these CPPMs are capable of efficient enantioseparation of drug enantiomers via directional H-bonding interactions and create a novel chiral membrane separation system. Download figure Download PowerPoint Introduction Driven by the needs of modern pharmacological science for single enantiomers, the chiral resolution of racemates that cannot be synthesized in a specific enantiomeric form has been the subject of intensive study1–4 since the biochemical behavior and toxicity of individual enantiomers are often quite different.5,6 Traditional methodologies for the separation of enantiomers include crystallization of diastereomeric salts,7 chromatography methods [such as high-performance liquid chromatography (HPLC) and supercritical fluid chromatogram (SFC)],8,9 and enzymatic resolution.10 The key to achieving efficient chiral resolution is to develop efficient, robust, and scalable chiral separation materials. Known enantioseparation materials include chiral polymer-based nanoassemblies,11–13 metal–organic frameworks (MOFs),14–16 covalent organic frameworks (COFs),17–19 molecular cages,20–22 and so forth. However, with respect to the practical separation of enantiomers, existing materials and methods suffer from one or more of the following problems: high cost and synthetic challenges; low stability and a time-consuming process; and the fact that they are not always applicable for preparative-scale yields due to their limitation to small areas. Currently, membrane-based chiral separation is of considerable interest, mainly because of its significant advantages of simplicity, throughput, and low generation of waste.23 The exploration of efficacious chiral porous membranes is unequivocally at the heart of this advanced technology. In doing so, numerous attempts have been made to develop various chiral membranes, such as chiral COFs, MOFs and their composites,24–26 polyelectrolyte membranes,27 and carbon nitride hybrid membranes.28 Regrettably, most of these cannot achieve complete chiral recognition and separation because their chiral selectivity cannot be tuned or controlled.29 The usefulness of a chiral membrane for the envisioned application can be determined by (1) the uniformity of the enantioselective site distribution throughout the membrane and pore architecture, as these will inevitably influence enantioseparation efficiency; (2) the interaction of the enantioselective center and the enantiomers, as this is vital to the overall enantioselectivity; and (3) the practicability of preparative-scale separation. Poly(ionic liquid)s (PILs) refer to a special type of functional polyelectrolytes that take along an IL species in each of the repeating units.30 Benefiting from the unique characters of ionic liquid and macromolecular architecture (such as processability, durability, and mechanical/thermal stability), PILs have recently sparked steadily expanding interest in the fields of polymer chemistry and materials science, and particularly the field of membrane science.31,32 In Nature’s biochemical systems, the key features of biologically active molecules are chiral NH functionality-based recognition and selective binding.33,34 Inspired by these fascinating natural structures, we herein designed an innovative method to synthesize chiral porous polymer membranes (CPPMs) bearing chiral NH groups by crosslinking single-component chiral PILs with H2O molecules via H-bonding. We demonstrate that these CPPMs are capable of efficient enantioselective separation of drug enantiomers via directional H-bonding interactions. Results and Discussion Figures 1a and 1b show the synthetic procedure of CPPMs and the structural model of the chiral PIL. Details of material synthesis and structural characterizations are included in the Supporting Information Figures S1−S12. In a typical membrane fabrication procedure, a dimethyl sulfoxide (DMSO) solution of single chiral poly(1-l-phenylglycinyl-3-vinylimidazolium bistrifluoromethanesulfonimidate [TFSI]) (l-PVImPhgTFSI) or poly(1-d-phenylglycinyl-3-vinylimidazolium TFSI) (d-PVImPhgTFSI) was cast onto a glass mold, dried for 6 h at 90 °C, and finally immersed in water for 15 min to build up the CPPMs ( Supporting Information Figure S13). Notably, the construction was performed via a bottom-up method, and only water was used to create the pores, allowing this approach to be straightforward, eco-friendly, and scalable in size and quantity. Figure 1 | Schematic illustration of the synthetic procedure for CPPMs and the structural model of the chiral PILs. Download figure Download PowerPoint For simplification, the CPPMs composed of l-PVImPhgTFSI and d-PVImPhgTFSI were dubbed l-CPPM and d-CPPM, respectively. Figure 2a shows the cross-sectional scanning electron microscopy (SEM) image of l-CPPM, from which it can be clearly seen that a gradient, three-dimensionally interconnected macropore architecture was created. The pore size gradually decreased from 2.6 ± 0.25 μm to 2.2 ± 0.3 μm to 1.0 ± 0.28 μm from the top to the bottom (from zones I and II to III; see Figure 2a and Supporting Information Figure S14), respectively. A high-magnification SEM image (Figure 2b) clearly reveals that hierarchical pores were formed within l-CPPM, which was composed of gradient macropores and nanopores with an average size of 0.6 ± 0.18 μm, agreeing well with the observation from the surface SEM image of l-CPPMs (Figure 2c). Importantly, such a hierarchical pore architecture was seriously pursued in the adsorption and separation field because nanopores are beneficial and provide active surface areas with high accessibility, and macropores form interconnected three-dimensional networks, serving as transport highways to accelerate mass diffusion and significantly promote exchange efficiency. As expected, the pore architecture and size of d-CPPM are very analogous to those of l-CPPM (Figures 2d–2f and Supporting Information Figure S15). This observation is reasonable because the l,(d)-CPPMs are fabricated from structurally identical PILs under the same conditions. The only difference is the chirality of the l,(d)-CPPMs, which will be discussed in detail later. Figure 2 | Low- and high-magnification cross-sectional SEM images of (a and b) l-CPPM and (c and d) d-CPPM. (e and f) Surface SEM image of l-CPPM and d-CPPM, respectively. (g) Representative in situ fluorescence LSCM images of l-CPPM doped with 20 ppm 1,1′-dioctadecyl-3,3,3′3′-tetramethyl indocarbo-cyanineperchlorate (its chemical structure is provided in Supporting Information Figure S16) illuminated at 405 nm before and after contact with water; scale bar: 5 μm. (h) 1H NMR spectrum of l-PVImPhgTFSI in different solvents (experimental conditions: 10 mg of l-PVImPhgTFSI in 0.6 mL DMSO-d6 vs 10 mg of l-PVImPhgTFSI in a mixed solvent of 0.1 mL of D2O and 0.5 mL of DMSO-d6). Download figure Download PowerPoint To shed light on the CPPM construction process, in situ laser scanning confocal experiments were conducted. Taking l-PVImPhgTFSI as an example, as shown in Figure 2g, before the dried l-PVImPhgTFSI film made in contact with water, a trace of the fluorescent, DMSO-soluble, water-insoluble dye molecule 1,1′-dioctadecyl-3,3,3′3′-tetramethyl indocarbo-cyanineperchlorate was homogeneously distributed throughout the transparent l-PVImPhgTFSI film. In stark contrast, it can be clearly seen that the pores gradually developed during the first 20 s and developed rapidly within 15 min after a drop of water was cast on the transparent l-PVImPhgTFSI film. These results showed that the pores in the l-CPPM stem from H2O-induced phase separation of the homopolymer l-PVImPhgTFSI. Self-assembly of amphiphilic block polymers via rinsing with a selective solvent and the removal of additives and/or a template to form porous membranes has been reported in polymer materials science.35,36 Such facile toxic-organic solvent-free phase separation-induced formation of porous membranes from homopolymers is, however, difficult to achieve. Previous theoretical calculations demonstrated that the introduction of H2O molecules into hydrophobic PILs could weaken the coulombic interactions between oppositely charged ions and result in the aggregation of polycations via preferential H-bonding interactions, which would eventually lead to a strong phase separation of polar and nonpolar domains in polycationic chains.37 To deeply investigate the H-binding interaction mode of H2O molecules and chiral PILs, proton nuclear magnetic resonance (1H NMR) experiments were conducted in different solvent environments. The black line in Figure 2h displays the 1H NMR spectrum of l-PVImPhgTFSI in DMSO-d6. The –NH and C2 proton signals in the imidazolium ring are clearly observed at approximately 9.4 ppm. Interestingly, the two proton signals at approximately 9.4 ppm highlighted by asterisks disappeared in a D2O/DMSO-d6 mixture (v/v=1:5) solvent due to the well-known H/D exchange process. As shown in Supporting Information Figure S17, a similar result was also observed for d-PVImPhgTFSI. These experimental results indicated that the N–H site and C2 proton in the imidazolium ring are highly active and interact with H2O molecules. In addition, it is well known that the proton of –COOH is active, although it was not measured in our 1H NMR experiments. Based on these analyses, we reasoned that the main H-bonding interactions of l-PVImPhgBr or d-PVImPhgBr with H2O occurred at the C2 proton in the imidazole ring, the chiral –NH site, and the –COOH group. To probe the original chirality of CPPMs, both the single crystals of l-PVImPhgBr and d-PVImPhgBr were carefully determined by X-ray single-crystal diffraction. Single-crystal structure analyses indicate that both l-PVImPhgBr and d-PVImPhgBr exhibit monoclinic structures belonging to the P2(1)/c group. The detailed cell parameters of l-PVImPhgBr and d-PVImPhgBr are listed in Supporting Information Table S1. The single-crystal structures show that anionic Br is located on the right and left sides of the cationic structures of l-PVImPhgBr and d-PVImPhgBr, respectively (Figures 3a and 3b and Supporting Information Figures S21 and S22). Additionally, as shown in Figures 3c and 3d, the stacking modes revealed that the imidazolium rings and benzene rings form a parallel structure through π–π interactions with a face-to-face distance of 6.521 Å in both l-PVImPhgBr and d-PVImPhgBr ( Supporting Information Figure S23). Notably, the Br ions in l-PVImPhgBr and d-PVImPhgBr are mirror images of each other and do not overlap. These results unambiguously confirm the enantiomer conformations of l-VImPhgBr and d-VImPhgBr. Figure 3 | (a and b) Single-crystal structures of l-VImPhgBr and d-VImPhgBr, respectively. (c and d) Stacking modes of l-VImPhgBr and d-VImPhgBr, respectively. Solution CD spectra of (e) l-PVImPhgBr and d-PVImPhgBr and (f) l-PVImPhgTFSI and d-PVImPhgTFSI. (g) solid-state CD spectra of l-CPPM and d-CPPM. The chemical structure of achiral PIL and SEM images of its porous membrane are provided in Supporting Information Figures S18–S20. Download figure Download PowerPoint Solution circular dichroism (CD) spectroscopy is a classical and robust tool for analyzing both molecular and supramolecular chirality. As shown in Figure 3e, the CD spectra of l-PVImPhgBr and d-PVImPhgBr displayed a strong Cotton effect at approximately 225 nm, demonstrating that the chirality of the monomers was well maintained throughout the polymerization process in DMSO solution at 90 °C. Additionally, it was found that l-PVImPhgTFSI and d-PVImPhgTFSI exhibited a distinct Cotton effect at approximately 235 nm (Figure 3f), suggesting that the metathesis reaction (Br → TFSI) has no effect on the chirality of PILs. These results demonstrate the excellent stereochemical stability of chiral ionic liquid monomers and their corresponding PILs even in organic solvents at high temperature or in saline solutions that were otherwise previously shown to easily racemize the stereocenter of the bromide salt.38 Solid-state CD spectra (Figure 3g) reveal that l-CPPM and d-CPPM exhibit opposite Cotton effects in the broad wavelength range of 210−310 nm, indicating the formation of left- or right-handed CPPMs. As observed, the solid-state CD spectra of the CPPMs exhibited broad peaks that were redshifted in comparison to those of chiral PILs in the solution state; this redshift most likely arises from the strong π–π interactions and intermolecular coupling of the chiral PIL crosslinked by H2O molecules.39 Taking the integrated information derived from the aforementioned analytical techniques into account, we considered that the different H-bonding interaction directions of l-PVImPhgBr and d-PVImPhgBr may be responsive to the positive and negative Cotton effect responses of the l-CPPM and d-CPPM, respectively, and the enantioselective sites are supposed to be homogeneously distributed throughout the CPPMs because they are composed of single-component chiral PILs. Given the distinct –NH chirality, directional H-bonding interaction, uniform distribution of the chiral sites and hierarchical pore architecture of the CPPMs, we were interested in exploiting their functions for the enantioselective separation of racemic drugs, a use that is particularly important in the pharmaceutical industry.40 Pure d-(–)-2-amino-3-mercapto-3-methylbutyric acid, conventionally called d-penicillamine, is becoming increasingly important as a fundamental therapeutic in the long-term treatment of immunological diseases, chronic aggressive hepatitis, and multiple sclerosis.41 In contrast, the racemate and the l-isomer are toxic. d-Penicillamine is now industrially manufactured by total synthesis of the racemate, and thereafter chiral resolution is achieved mostly through crystallization of the racemic penicillamine derivatives. Here, the advantage of these CPPMs for chiral resolution of (d,l)-penicillamine is demonstrated, as a proof of concept, by simply immersing a piece of l-CPPM or d-CPPM (Figures 4a and 4b) with a size of 1 × 1.25 cm and a thickness of 105 μm in 4 mL of 1 mM racemic penicillamine aqueous solution n. After immersing l-CPPM in racemic penicillamine solution, the CD spectra of the solution exhibited the adsorption signal of l-penicillamine, and the intensity was gradually increased with adsorption times, suggesting that l-CPPM is preferable for binding with d-penicillamine. Analogously, we found that d-CPPM is affiliative to l-penicillamine, which is indicated by the increased CD signal of d-penicillamine after immersion of d-CPPM in racemic penicillamine solution (Figure 4c). Chiral HPLC analyses showed that the e.e.% of l-penicillamine and d-penicillamine gradually increased with increasing adsorption time and reached up to 21.96% and 14.28% after 24 h of adsorption, respectively (Figure 4d). 1H NMR spectra confirmed strong H-bonding interactions between the active H-sites of l-CPPM and d-penicillamine ( Supporting Information Figure S24). Therefore, it is considered that the original enantioselectivity results from more favorable H-bonding interactions between the (d,l)-penicillamine and the CPPMs of the opposite chirality. Figure 4 | (a and b) Illustration of the l-CPPM and d-CPPM and their chemical structures. (c) CD spectra over adsorption times when l-CPPM or d-CPPM is immersed in the penicillamine aqueous solution. (d) Measured enantiomeric excess of l,(d)-penicillamine as a function of adsorption times. Download figure Download PowerPoint Conclusion An innovative, simple, and easily scalable synthetic strategy to produce CPPMs by crosslinking single chiral PILs with H2O has been developed. These well-defined CPPMs could enantioselectively separate penicillamine enantiomers via directional H-bonding interactions. Considering the designability of PIL chemical structures, we envision that this straightforward fabrication strategy could be exploited in the formulation of diverse useful chiral porous membranes by judicious choice of the chiral PIL chemical structures. By catering to the specific interactions (such as van der Waals forces, H-bonding, ionic attraction, charge-transfer complexation, and host–guest inclusion phenomena) of the chiral centers of the CPPMs with enantiomers, this strategy may find substantial use in chiral resolution. Supporting Information Supporting Information is available and includes materials and methods, synthesis and characterizations, experimental procedures and supporting figures and table including 1H/13C-NMR spectra, TGA/DSC spectra, GPC spectra, digital photos, crystallographic data for l-ImPhgBr and d-ImPhgBr CCDC 2069493-2069494, and X-ray crystallographic data for l-ImPhgBr and d-ImPhgBr. Conflict of Interest There is no conflict of interest to report. Funding Information This research was financially supported by the Nankai University, the National Science Foundation of China (grant no. 21875119), and the Natural Science Foundation of Tianjin (19JCYBJC17500). This work is dedicated to the 100th anniversary of chemistry at Nankai University. References 1. Li P.; He Y.; Guang J.; Weng L.; Zhao J. C.; Xiang S.; Chen B.A Homochiral Microporous Hydrogen-Bonded Organic Framework for Highly Enantioselective Separation of Secondary Alcohols.J. Am. Chem. Soc.2014, 136, 547–549. 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S.D-Penicillamine-Production and Properties.Angew. Chem. Int. Ed.1975, 14, 330–336. Google Scholar Previous articleNext article FiguresReferencesRelatedDetails Issue AssignmentVolume 4Issue 9Page: 2930-2937Supporting Information Copyright & Permissions© 2022 Chinese Chemical SocietyKeywordschiralityhydrogen-bondingpoly(ionic liquid)porous membranehierarchical architecture Downloaded 1,087 times PDF DownloadLoading ...