Chiral Recognition Site Research Articles

Supramolecular Interaction Modulation in Thermosensitive Composites: Enantiomeric Recognition and Chiral Site Regeneration.

Herein, a novel strategy was implemented to modulate the supramolecular interaction between enantiomers and chiral recognition sites (CRSs), effectively resolving the issue of CRS saturation. Randomly methylated-β-cyclodextrin (Rm-β-CD) was used as the CRS (host molecule), and polymerized ionic liquids [poly([vbim]TFSI)] were used as the supramolecular modulator (guest molecule), which self-assembled to generate thermosensitive supramolecular host/guest complexes. The enantiomeric binding capacity and enantioselectivity of chiral separation systems centered on supramolecular host-guest complexes are characterized by a high degree of temperature dependence. Poly([vbim]TFSI) bonded to Rm-β-CD at temperatures between 17 °C ± 3 and 50 °C ± 3 °C, and the binding free energy difference (|ΔΔG|) between the (S)- and (R)-enantiomer was 0.55. Conversely, poly([vbim]TFSI detached from Rm-β-CD at temperatures >50 °C ± 3 °C or <17 °C ± 3 °C, and |ΔΔG| between (S)- and (R)-enantiomer was 0.03. The |ΔΔG| value of the (R)-enantiomer can reach 0.86 in two temperature intervals. Therefore, the binding of poly([vbim]TFSI) to Rm-β-CD afforded the favorable separation of four racemic sample mixtures: mandelic acid (e.e.% = 61.3%), ibuprofen (e.e.% = 21.6%), warfarin (e.e.% = 14.9%), and naproxen (e.e% = 18.2%). The detachment of poly([vbim]TFSI) from Rm-β-CD released the enantiomer bound to CRSs. The decomplexation of mandelic acid reached 75.1%.

A novel approach to chiral separation: thermo-sensitive hydrogel membranes.

The application of membrane technology for separating chiral compounds is hindered due to the restricted availability of chiral recognition sites on the membrane surface. In this study, we propose a novel approach for chiral separation through a selector (bovine serum albumin, BSA) mediated thermo-sensitive membrane system. A thermo-sensitive hydrogel-coated membrane (termed PDTAN) was developed by anchoring poly(N-isopropylacrylamide) (PNIPAm) onto a polyethersulfone (PES) membrane through an adhesive and hydrophilic dopamine hydrochloride (PDA)/tannic acid (TA)/chitosan (Chi) intermediate layer. The results demonstrate outstanding chiral separation efficiency, achieving αL/D = 3.30 for D-phenylalanine (D-Phe) rejection at 40 °C on a BSA-mediated PDTAN membrane system, with significant stability and minimal fouling, surpassing previous findings. Moreover, the PDTAN membrane altered the selective properties of recognition sites in BSA, transitioning from rejecting L-Phe to rejecting D-Phe. Analysis using fourth-order derivative UV-vis, circular dichroism (CD), and in situ Fourier transform infrared spectroscopy (FTIR) techniques revealed a transition in the secondary structure of BSA from α-helix to β-sheet as the temperature increased. This transition, facilitated by hydrogen bonding between BSA and PNIPAm, enabled selective recognition of D-Phe, demonstrating a distinct shift in chiral recognition properties. Importantly, with D-Phe adsorbed onto β-sheet structures of BSA, hydrogen-bond interactions between BSA and the PDTAN membrane were significantly reduced, thereby minimizing membrane fouling and achieving the durability of membrane-based chiral separation.

Fabrication of a ratiometric fluorescence nanoprobe for detecting tryptophan enantiomers

A novel ratiometric fluorescence nanoprobe was developed to detect tryptophan enantiomers with high selectivity and sensitivity. Fluorescein (FL) was doped into SiO2 nanoparticles with little dye leakage, acting as an internal reference signal. The chiral center of L-histidine (L-His) was introduced by partially replacing the carboxyl on the surface of SiO2. The response signal of Eu3+ was coordinated with carboxyl to obtain the FL@SiO2-Eu/His nanoprobe. The nanoprobe shows enantioselective luminescence responses for tryptophan enantiomers. The red emission of Eu3+ can be effectively quenched by the tryptophan enantiomers, but the quenching efficiency is different due to the different interactions with the chiral recognition sites. The fluorescence intensity ratio (I613/I515) shows excellent linearity with tryptophan enantiomers in the range of 0–100 μM (R2 > 0.99). The limit of detection (LOD) is 1.0 μM and 1.3 μM for L-tryptophan (L-Trp) and D-tryptophan (D-Trp), respectively. The FL@SiO2-Eu/His nanoprobe shows good selectivity and specific recognition in serum actual samples. In addition, the nanoprobe can realize visual detection under UV light due to the obvious color change. This work provides an innovative idea for the development of new probes in the detection field.

Research Progress of Chiral MOFs in Chiral Resolution

Chiral separation is important for drug development, and chiral resolution is one of the most popular methods for chiral separation. Metal organic framework materials (MOFs), with their regular and adjustable porous structures, can be an efficient and selective platform for chiral recognition and separation by assigning highly ordered chiral recognition sites to MOFs with large specific surface area and high stability. This paper reviews the recent literature on the synthesis and application of chiral MOFs and the preparation and application of MOFs composites. Firstly, the progress of MOFs synthesis methods in recent years is introduced, followed by the progress of the application of post-functionalized chiral MOFs in chiral resolution, and then the progress of the preparation and application of MOFs complexes is also introduced. Finally, the limitations and developments of chiral MOFs in chiral drug resolution are briefly described in this paper.

Synthesis of Cyclodextrin-based MOFs incorporating amino acid chiral ligands for chiral separation of naproxen enantiomers

The design of adsorbent materials capable of efficiently separating chiral molecules were a promising way to achieve selective recognition and separation of racemic enantiomers. Here, a γ-Cyclodextrin (γ-CD) based metal–organic framework (MOF) with D-Histidine (D-His) as a chiral ligand was synthesized for the first time to construct a functional chiral adsorption separation material (D-His@γ-CD-MOF), which can be used as an adsorbent for Naproxen enantiomer (S-/R-Npx). D-His@γ-CD-MOF provided a large number of chiral recognition sites for the selective enrichment of S-Npx based on the realization of the spatial advantage of the MOF structure, and the e.e. % value of a single separation of Npx racemates could reach 20.0 %. Meanwhile, the intermolecular binding patterns were predicted by computer simulations, and the chiral adsorption was attributed to the difference in affinity due to the difference in π-lone pair miscellaneous and hydrogen bonding force capacities of D-His@γ-CD-MOF and S-/R-Npx. Therefore, considering the stereospecific structure of D-His@γ-CD-MOF as well as the lone pair electron and hydrogen bonding coordination ability, it has great prospects for application as a chiral resolution agent.

Highly Improved Chiral-Selective Resolution in Pillar[5]arene-Functionalized Molecularly Imprinted Membranes

It is a challenging task to achieve the effective separation of chiral compounds under simple and rapid conditions. In order to solve this problem, this study used the molecularly imprinted membrane (MIM) technology developed on the basis of biological semi-permeable membranes, using S-triadimefon as the template molecule, and successfully prepared MIMs by photo-initiated polymerization. By adding macrocyclic molecular 1,4-bis(allyloxy)pillar[5]arene as a functional monomers, the effectiveness of the chiral recognition sites of the target molecules is improved, thereby improving the chiral selectivity of the MIM and optimizing the molar ratio of template molecules, monomers, and cross-linkers. On this basis, the separation effect of non-MIM (NIM), single-monomer MIM (MIM-I), and two-monomer MIM (MIM-II) on triadimefon enantiomers was investigated. It was found that the enantiomer excess (e. e.) % value of MIM-I is larger than that of NIM, but the value of MIM-I is still very low. When pillar[5]arene, a macrocyclic molecule was added as the second monomer, its e. e. % increased from 27.4 to 84.8%.

Superficial chiral etching on an achiral metal-organic framework for high-performance liquid chromatography enantioseparations.

Chiral metal-organic frameworks have shown great potential in enantioselective separation and asymmetric catalysis due to their diverse and adjustable structures with abundant chiral recognition sites. Herein, a new chiral post-synthetic modification was used for preparing an achiral@chiral metal-organic frameworks core-shell composite [Cu3 (Btc)2 ]@[Cu2 ((+)-Cam)2 Dabco] by a superficial chiral etching method. The [Cu3 (Btc)2 ]@[Cu2 ((+)-Cam)2 Dabco] composite was utilized as a novel chiral stationary phase for HPLC enantioseparation. Various racemates were separated on the [Cu3 (Btc)2 ]@[Cu2 ((+)-Cam)2 Dabco]-packed column (column A). It exhibited good chiral resolving ability toward many different kinds of racemates, especially chiral drugs. Among them, the highest resolution value for 1,2-diphenyl-1,2-ethanediol reaches 2.70. The relative standard deviations of retention time and peak area for repeated separation of 1,2-diphenyl-1,2-ethanol were 0.45% and 0.81%, respectively. Compared with the resolution ability of [Cu2 ((+)-Cam)2 Dabco]-packed column (column B), column A shows higher column efficiency and better separation performance than those of column B. The results indicated that the [Cu3 (Btc)2 ]@[Cu2 ((+)-Cam)2 Dabco] as a stationary phase can greatly improve the column efficiency and chiral resolution ability of chiral metal-organic frameworks, which demonstrated that the superficial chiral etching as an economic and efficient strategy opens up a new way for the application of metal-organic frameworks.

Zirconium Metal Organic Framework-Based Hybrid Sensors with Chiral and Luminescent Centers Fabricated by Postsynthetic Modification for the Detection and Recognition of Tryptophan Enantiomers.

By immobilizing the chiral center l-histidine (l-His) into a Zr-based metal-organic framework (MOF) through post-synthetic ligand exchange, a chiral compound MOF-His has been prepared. On this basis, MOF-His is hybridized with Eu3+ ions to obtain the final responsive compound Eu@MOF-His. It is worth noting that the bifunctional material exhibits enantioselective luminescence properties for tryptophan enantiomers. The experimental results demonstrate that tryptophan enantiomers can effectively quench the red-light emission of Eu3+ ions, and also, the quenching rates are various, which may originate from the differences in the interaction between analytes and chiral recognition sites. In addition, Eu@MOF-His can realize the sensing of tryptophan enantiomers in serum. Concurrently, the compound possesses reusability, high sensitivity, and fast response speed, which means that it has the potential to serve as an excellent fluorescent sensor for detecting and identifying tryptophan enantiomers.

Enhanced Chiral Recognition Abilities of Cyclodextrin Covalent Organic Frameworks via Chiral/Achiral Functional Modification.

β-Cyclodextrin covalent organic frameworks (β-CD COFs) show great potential in enantioseparation due to their uniformly distributed chiral recognition sites and good chemical stability. The hydroxyl and amino groups of β-CD COFs enable facile post-modification to introduce the desired functionality into the frameworks. In this study, we perform post-modification of β-CD COFBPDA with 1,4-butane sultone and [(3R,4R)-4-acetyloxy-2,5-dioxooxolan-3-yl] acetate to construct two kinds of novel functional β-CD COFs. The capillary columns prepared with these two functional β-CD COFs separated chiral dihydropyridines and fluoroquinolones with excellent selectivity and repeatability in capillary electrochromatography, while β-CD COFBPDA-modified capillary columns did not present the chiral recognition ability for these drugs. The mechanism of chiral recognition and the enhanced enantioselectivity of functional β-CD COFs were further demonstrated by molecular docking simulation. The divergent chiral separation performances of β-CD COFs suggest that the introduction of functional groups enables the modification of β-CD COF properties and tuning of its chiral recognition abilities for the diversity of enantioseparation.

Fabrication of PVDF-blended ultrafiltration membranes incorporated by chiral mesoporous silica for enantioseparation

Novel poly(vinylidene fluoride) (PVDF) ultrafiltration membranes blending with chiral mesoporous SiO2 materials were constructed to improve the anti-fouling and separation performance of PVDF-blended membranes. The formation of asymmetric mesoporous structure of chiral mesoporous SiO2 caused their large hydrophilic surface and significant chiral features, which enhanced the hydrophilicity and polarity of the resulting PVDF membranes blended with chiral mesoporous SiO2. So, the PVDF-blended membranes containing chiral mesoporous SiO2 had a high permeation performance and anti-fouling property. After blending with chiral mesoporous SiO2, the maximum flux of membranes exceeded 500 L·m−2·h−1 and was 6.5-fold higher than that of neat PVDF. Due to the stereo-specific interaction between enantiomers and chiral recognition sites introduced by chiral mesoporous SiO2 in the membranes, all PVDF-blended membranes had evident enantioseparation performance for DL-racemic tryptophan. The C-SiO2-20/PVDF-blended membranes had the highest enantioseparation performance under the same addition content and the maximum enantiomeric excess (e.e.%) was more than 20 %. Given the strong stereo-specific interaction and hydrogen bonding between d-tryptophan and β-cyclodextrin (β-CD), the addition of more β-CD would introduce more chiral recognition sites into the membranes, thereby enhancing the enantioseparation performance of the membranes for d-tryptophan. The maximum e.e.% of C-SiO2-20/β-CD/PVDF-blended membranes for the tryptophan enantiomer reached 55%.

Self-assembled monolayer protection of chiral-imprinted mesoporous platinum electrodes for highly enantioselective synthesis.

In modern chemistry, chiral (electro)catalysis is a powerful strategy to produce enantiomerically pure compounds (EPC). However, it still struggles with uncontrollable stereochemistry due to side reactions, eventually producing a racemic mixture. To overcome this important challenge, a well-controlled design of chiral catalyst materials is mandatory to produce enantiomers with acceptable purity. In this context, we propose the synergetic combination of two strategies, namely the elaboration of mesoporous Pt films, imprinted with chiral recognition sites, together with the spatially controlled formation of a self-assembled monolayer. Chiral imprinted metals have been previously suggested as electrode materials for enantioselective recognition, separation and synthesis. However, the outermost surface of such electrodes is lacking chiral information and thus leads to unspecific reactions. Functionalising selectively this part of the electrode with a monolayer of organosulfur ligands allows an almost total suppression of undesired side reactions and thus leads to a boost of enantiomeric excess to values of over 90% when using these surfaces in the frame of enantioselective electrosynthesis. In addition, this strategy also decreases the total reaction time by one order of magnitude. The study therefore opens up promising perspectives for the development of heterogeneous enantioselective electrocatalysis strategies.

L-histidine-regulated zeolitic imidazolate framework modified electrochemical interface for enantioselective determination of L-glutamate

Metal-organic framework (MOF)-based electrochemical interface presents a broad platform for the chiral recognition of amino acids, but the inferior conductivity of most MOFs limits the sensitivity in practical applications of electrochemical sensing. Therefore, the L-histidine-regulated zeolitic imidazolate framework (L-His-ZIF) was proposed as a novel electrochemical interface for simple, efficient, and enantioselective determination of L-glutamate (L-Glu) based on the electrochemical impedance spectroscopy (EIS). Based on the resistance change, the L-His-ZIF interface can be directly used for chiral recognition without the assistance of high-conductive substances, where multiple immobilizations are generally required in MOF-involved voltammetry. The stacked L-His-ZIF nano-polyhedrons provided numerous cavities and high specific surface area, thereby forming adequate chiral recognition sites. Based on the L-His-ZIF interface, the enantioselective detection of l-Glu-was successfully achieved with a good linear relationship with the impedance difference in the range from 0.1 nM to 50 nM with the detection limit of 0.06 nM. This prepared ZIF-functionalized electrode provided the desired enantioselectivity and reproducibility with robust chiral recognition in the real application. More importantly, MOF-modified EIS can be applied for more chiral recognition of enantiomers by various MOF interfaces, which has great potential for applications in pharmaceutical monitoring and biochemical analysis.

Artificial Metal-Peptide Assemblies: Bioinspired Assembly of Peptides and Metals through Space and across Length Scales.

The exploration of chiral crystalline porous materials, such as metal-organic complexes (MOCs) or metal-organic frameworks (MOFs), has been one of the most exciting recent developments in materials science owing to their widespread applications in enantiospecific processes. However, achieving specific tight-affinity binding and remarkable enantioselectivity toward important biomolecules is still challenging. Perhaps most critically, the lack of adaptability, compatibility, and processability in these materials severely impedes practical applications in chemical engineering and biological technology. In this Perspective, artificial metal-peptide assemblies (MPAs), which are achieved by the assembly of peptides and metals with nanometer-sized cavities or pores, is a new development that could address the current bottlenecks of chiral porous materials. Bioinspired assembly of pore-forming MPAs is not foreign to biological systems and has granted scientists an unprecedented level of control over the chiral recognition sites, conformational flexibility, cavity sizes, and hydrophilic segments through ultrafine-tuning of peptide-derived linkers. We will specifically discuss exemplary MPAs including structurally well-defined metal-peptide complexes and highly crystalline metal-peptide frameworks. With insights from these structures, the peptide assembly and folding by the closer cooperation of metal coordination and noncovalent interactions can create adaptable protein-like nanocavities undergoing a myriad of conformational variations that is reminiscent of enzymatic pockets. We also consider challenges to advancing the field, where the deployment of side-chain groups and manipulation of amino acid sequences are more likely to access the programmable, genetically encodable peptide-mediated porous materials, thus contributing to the enhanced enantioselective recognition as well as enabling key biochemical processes in next-generation versatile biomimetic materials.

Metal‐Organic Frameworks as a New Platform for Enantioselective Separations

AbstractThe enantioselective separation of racemic mixtures is highly important in the pharmaceutical, food and agrochemical sector. Metal‐organic frameworks, as a class of highly porous materials are emerging as highly efficient and selective platforms for chiral recognition and separation owing to their ultrahigh porosities, functionalized pore walls, controllable pore chemistry and presence of highly ordered chiral recognition sites. In this review, we summarize the progress made in the synthesis of chiral MOFs via direct and indirect methods, followed by their applications in some important chiral separations of alcohols, drugs, amino acids, biologically relevant molecules and important chiral organic mixtures. The developments in chiral MOF membranes as thin films for practical industrial use are also explored. Finally, the outlook for the MOFs as emerging platforms for enantioseparation and the future directions are discussed.

Bovine serum albumin-coated titanium dioxide modified electrochemical interface for enantioselective discrimination of D/L-aspartic acid.

Due to the similar physicochemical properties, the discrimination of chiral isomers faces huge challenges in drug production and biochemical analysis. Herein, the bovine serum albumin-coated titanium dioxide (bovine serum albumin [BSA]/TiO2 ) was modified as a novel electrochemical interface for efficient, simple, and enantioselective discrimination of aspartic acid enantiomers (D/L-Asp) based on the electrochemical impedance spectroscopy (EIS). Utilizing the structural characteristics of large cavity and high specific surface area, TiO2 material provided sufficient space for adequate loading of BSA. The BSA/TiO2 electrochemical interface was successfully fabricated to support abundant chiral recognition sites. The enantioselective discrimination of D/L-Asp was achieved on the interface with a good linear relationship against the impedance difference in the concentration range from 1 to 1000 nM with the detection limit of 0.37 nM for L-Asp and 0.94 nM for D-Asp, reaching the identification coefficient (Ic = KL /KD ) of 1.85. The proposed interface is easy to form with a stable formation of BSA in TiO2 microporous architecture, which maintained the desired stability and reproducibility. For the unknown racemic solution, Ic levels of different enantio-ratios of D/L-Asp were effectively obtained to evaluate the chiral percentage of racemic sample. The possible mechanism of chiral recognition by density function theory (DFT) was confirmed with a stronger adsorption to L-Asp in accordance with our experiment results, reinforcing the validity of our presented interface. The BSA/TiO2 electrochemical interface with robust enantioselective discrimination of D/L-Asp has great potential for the practical application in pharmaceutical surveillance and food security.

Cyclodextrins as Dominant Chiral Selective Agents in the Capillary Separation Techniques

This review paper shows the dominant role of the cyclodextrins in the chiral separations using capillary columns (GC, SFC, CE). The cyclodextrins (CDs) have extremely broad chiral selectivity spectra because they have several different chiral recognition sites in various arrangements and various interaction modes. Their chiral selectivity features can further improve with their various substitutions. Their selectivities are moderate therefore they need high efficiency separations (capillary columns) for good chiral resolutions. The shape selectivity of cyclodextrins is also shown with non-chiral isomers too. The utility of the cyclodextrins is demonstrated with several examples based on the personal observations of authors and critical review of literature. The theoretical backgrounds of their chiral recognitions (e.g. H-bond interaction, inclusion, induced fit) are discussed in depth. This paper is not application oriented but is dealing with mostly on the physical and chemical background of separations using CDs.

Chiral core-shell microspheres β-CD-COF@SiO2 used for HPLC enantioseparation

Chiral covalent organic frameworks (CCOFs) have potential application in enantioseparation due to their advantages, such as large surface area, abundant chiral recognition sites and good chemical stability in organic solvents. However, the application of CCOFs in high performance liquid chromatography (HPLC) for enantioseparation has been rarely reported because of the shortcomings of CCOFs, such as light weight, irregular shape, and wide particle size distribution. In order to overcome the above shortcomings, a one-pot synthetic method was adopted to prepare a core-shell composite (β-CD-COF@SiO2) via the growth of chiral β-CD COF on the surface of amino-functionalized SiO2 microspheres. The as-prepared β-CD-COF@SiO2 microspheres were used as a stationary phase for HPLC enantioseparation. The resolution ability of the β-CD-COF@SiO2-packed column toward various chiral compounds was investigated using n-hexane/isopropanol as the mobile phase. The results show that the chiral β-CD-COF@SiO2-packed column exhibited excellent chiral recognition ability for 24 pairs of chiral compounds with good reproducibility. These successful applications indicate that the preparation of the chiral COFs@SiO2 core-shell microspheres as a novel stationary phase for enantioseparation has good application prospects in HPLC.

Emerging Homochiral Porous Materials for Enantiomer Separation

AbstractEfficient resolution of racemates of chiral molecules is of great significance in the pharmaceutical, agrochemical, fragrances, and food additives industries. Emerging homochiral porous materials such as metal–organic frameworks, covalent‐organic frameworks, porous‐organic cages, and metal‐organic cages with ultrahigh surface area, controllable pore chemistry and ample chiral recognition sites are promising for efficient chiral resolution, which display excellent properties for chiral separation applications. This review summarizes the design and synthesis strategies for the construction of homochiral porous materials, including direct synthesis, post‐synthesis, and chiral induction synthesis. Following this, applications of emerging homochiral porous materials, including enantioselective adsorption, chiral chromatography, and membrane‐based chiral separation are highlighted. Finally, the challenges in this area are discussed, with future perspectives provided.

Chiroptical Cross‐Linked Polymers Grown via Radical Polymerization around Chiral Nanosilica

AbstractChiral polymers are often prepared by two ways depending upon chiral monomers, chiral catalysts, and chiral auxiliaries which always come from organics: one is the enantio‐selective polymerization of prochiral or racemic monomers or polymerization of optically active monomers; and the other one is the molecular imprinting technique, which creates chiral recognition sites inside a densely cross‐linked polymer gel. Herein, a unique method for the synthesis of chiroptical cross‐linked polymers via radical polymerization of achiral divinyl monomers in the mediation of the inorganic chiral nanosilica is reported. The monomers that are cross‐linkable such as divinylbenzene (DVB) and N,N′ ‐methylenebisacrylamide (MBA) are physically adsorbed onto chiral silica bundles and then polymerized by dispersion of those monomers/silica bundles in the presence of radical initiators. The products are characterized by SEM, FT‐IR, solid‐state 13C NMR, TGA, and CD. Very interestingly, the cross‐linked polymers themselves obtained via final removal of the chiral silica show remarkable chiroptical activity with mirror relationship and can make achiral guest of porphyrin adsorbed on the polymers become optically active.

Chiral Macroporous MOF Surfaces for Electroassisted Enantioselective Adsorption and Separation.

The development of surfaces with chiral features is a fascinating challenge for modern materials science, especially when they are used for chiral separation technologies. In this contribution, the design of hierarchically structured chiral macroporous zeolitic imidazolate framework-8 (ZIF-8) electrodes is presented. They are elaborated by an electrochemical deposition-dissolution technique based on the electrodeposition of metal through a colloidal crystal template, followed by controlled electrooxidation. This generates locally metal cations, which can interact with a chiral ligand present in the solution to form metal-organic frameworks (MOFs). The macroporous structure facilitates the access of the chiral recognition sites, located in the mesoporous MOF, and thus helps to overcome mass transport limitations. The efficiency of the designed functional materials for chiral adsorption and separation can be fine-tuned by applying an adjustable electric potential to the electrode surfaces. This hierarchical chiral ZIF-8 structure was deposited at the walls of a microfluidic device and used as a stationary phase for enantioselective separation. The potential-controlled interaction between the stationary phase and the chiral analytes allows baseline separation of two enantiomers. This opens up interesting perspectives for using hierarchically structured chiral MOFs as an efficient material for the selective adsorption and separation of chiral compounds.