Metal organic framework chiral material with core-shell structure as well as preparation method and application of metal organic framework chiral material

Abstract

The invention relates to a core-shell structure metal organic framework chiral material as well as a preparation method and application thereof, and relates to the technical field of chiral separation. The preparation method of the core-shell structure metal organic framework chiral material comprises the following steps: mixing dopamine hydrochloride and silicon dioxide according to a first preset mass ratio, and reacting under a first preset condition to obtain polydopamine modified silicon dioxide; and mixing dopamine modified silicon dioxide, a metal ion compound, an alkaline regulator, an organic ligand, a chiral ligand and deionized water according to a second preset mass ratio, and reacting under a second preset condition to obtain the core-shell structure metal organic framework chiral material. The preparation method of the core-shell structure metal organic framework chiral material has the characteristics of simplicity, low production cost and environmental friendliness, and a chromatographic column prepared from the core-shell structure metal organic framework chiral material has the advantages of low column pressure, high column efficiency and good separation effect on various racemic compounds.

Description

TECHNICAL FIELD

[0001] The present application relates to the technical field of chiral separation, more particularly, it relates to a core-shell structure metal organic framework chiral material and a preparation method and application thereof. BACKGROUND

[0002] Metal-Organic Frameworks (MOFs) are coordination polymers self-assembled from multidentate organic ligands containing oxygen, nitrogen, etc. and transition metal ions (or metal clusters), which have been synthesized as early as the 1990s. As a new type of functional material, MOFs have the characteristics of high porosity and specific surface area, diverse and designable structure, and adjustable and modifiable pore channels. The above characteristics endow MOFs with various important functions and extensive application prospects. With the rise of the research boom of functionalized MOFs, Chiral Metal-Organic Frameworks (CMOFs) have also been widely reported and rapidly applied in the fields of asymmetric catalysis, molecular recognition and enantiomeric separation. However, the application of CMOFs in chiral separation analysis is currently limited to laboratory research, and further research is needed to utilize the excellent properties of CMOFs to serve our production and life. SUMMARY

[0003] To solve the above technical problems, the present application provides a core-shell structure metal organic framework chiral material and a preparation method and application thereof.

[0004] According to a first aspect of the present application, a preparation method of a core-shell structure metal organic framework chiral material is provided, which adopts the following technical solution:

[0005] A preparation method of a core-shell structure metal organic framework chiral material, the preparation method comprises:

[0006] Dopamine hydrochloride and silicon dioxide are mixed according to a first preset mass ratio and reacted under a first preset condition to obtain polydopamine modified silicon dioxide;

[0007] Dopamine modified silicon dioxide, a metal ion compound, an alkaline adjusting agent, an organic ligand, a chiral ligand and deionized water are mixed according to a second preset mass ratio and reacted under a second preset condition to obtain the core-shell structure metal organic framework chiral material.

[0008] In some embodiments, the first preset mass ratio is 1:14.20-20.35.

[0009] In some embodiments, the second preset mass ratio is 3.0-8.0:1.5-6.5:1:1.0-4.0:1.0-4.0.

[0010] In some embodiments, the metal ion compound comprises one or more of zinc nitrate hexahydrate, zinc chloride, zinc acetate;

[0011] The basicity regulator comprises one or more of anhydrous sodium carbonate, triethylamine;

[0012] The organic ligand comprises one or more of 4,4'-bipyridine, terephthalic acid, 2-methylimidazole;

[0013] The chiral ligand comprises D-camphoric acid.

[0014] In some embodiments, the first preset condition comprises:

[0015] The reaction is carried out at a temperature of 20-30°C for 16-24h.

[0016] In some embodiments, the second preset condition comprises:

[0017] In the first stage, the mixture is stirred at a temperature of 20-30°C for 20-40min;

[0018] In the second stage, the reaction is carried out at a temperature of 115-125°C for 40-55h.

[0019] According to a second aspect of the present application, there is provided a core-shell metal organic framework chiral material, which is prepared by the preparation method of the core-shell metal organic framework chiral material according to any one of the above.

[0020] According to a third aspect of the present application, there is provided an application of a core-shell metal organic framework chiral material, wherein the core-shell metal organic framework chiral material prepared by the preparation method of the core-shell metal organic framework chiral material according to any one of the above or the core-shell metal organic framework chiral material according to the above is used as a chiral stationary phase of a chromatographic column for chiral separation of an external racemic compound.

[0021] In some embodiments, the external racemic compound comprises one or more of 1,1'-binaphthyl-2-ol, Troger's base, ibuprofen.

[0022] In some embodiments, when the external racemic compound comprises 1,1'-binaphthyl-2-ol, the flow rate of the mobile phase is 0.2-0.6mL / min;

[0023] When the external racemic compound comprises Troger's base, the flow rate of the mobile phase is 0.8-1.2mL / min;

[0024] When the external racemic compound comprises ibuprofen, the flow rate of the mobile phase is 0.3-0.7mL / min.

[0025] In summary, the application has the following beneficial effects:

[0026] 1. The application performs surface modification treatment on the silicon dioxide with dopamine hydrochloride to form a polydopamine layer on the surface of the silicon dioxide, which can improve the compatibility between the silicon dioxide and the metal organic framework, and the modification method has the advantages of simplicity and rapidity, does not need to use organic solvents such as toluene, and has the characteristics of environmental friendliness.

[0027] 2. The Zn-MOF@SiO2 column prepared in the application has the characteristics of low column pressure and high column efficiency, and has good separation performance for a variety of chiral compounds.

[0028] 3. The raw materials of the application are cheap, the production cost is low, and the application has high economic value. BRIEF DESCRIPTION OF DRAWINGS

[0029] The accompanying drawings, which are incorporated in and constitute a part of the specification, illustrate embodiments consistent with the application and, together with the description, serve to explain the principles of the application.

[0030] Figure 1 is a scanning electron microscope (SEM) image of the silicon dioxide (SiO2) in Example 1, core-shell structure metal organic framework chiral material (Zn-MOF@SiO2).

[0031] Figure 2a is a Fourier transform infrared spectroscopy (FT-IR) image of SiO2 in Example 1.

[0032] Figure 2b is an FT-IR image of Zn-MOF@SiO2 in Example 1.

[0033] Figure 3 is a high performance liquid chromatography (HPLC) image of the chiral stationary phase detecting 1,1'-binaphthyl-2-ol in Application Example 1, wherein the flow rate is 0.3 mL / min.

[0034] Figure 4 is a HPLC image of the chiral stationary phase detecting troger base in Application Example 2, wherein the flow rate is 1.0 mL / min.

[0035] Figure 5 is a HPLC image of the chiral stationary phase detecting ibuprofen in Application Example 3, wherein the flow rate is 0.5 mL / min.

[0036] Figure 6 is a HPLC image of the chiral stationary phase detecting 1,1'-binaphthyl-2-ol in Application Example 4, wherein the flow rate is 0.5 mL / min. DETAILED DESCRIPTION

[0037] In order to make the purposes, technical solutions and advantages of the embodiments of the present application clearer, the technical solutions of the present application will be described clearly and completely below in conjunction with the embodiments of the present application and the drawings. Obviously, the described embodiments are only some of the embodiments of the present application, rather than all the embodiments of the present application. Based on the embodiments in the present application, all other embodiments obtained by those skilled in the art without creative work fall within the scope of protection of the present application. It should be noted that, in the case of no conflict, the embodiments in the present application and the features in the embodiments can be combined with each other at will.

[0038] At present, the application of CMOFs as liquid chromatography stationary phase is mainly to directly use the synthesized CMOFs as the liquid chromatography stationary phase. However, due to the irregular shape of CMOFs, the prepared liquid chromatography column often has defects such as low column efficiency, high back pressure and poor peak shape.

[0039] In order to solve the above problems, an example embodiment of the present application provides a preparation method of a core-shell structure metal organic framework chiral material, which comprises:

[0040] S1, mixing dopamine hydrochloride and silicon dioxide according to a first preset mass ratio, and reacting under a first preset condition to obtain polydopamine modified silicon dioxide;

[0041] S2, mixing dopamine modified silicon dioxide, metal ion compound, alkaline adjusting agent, organic ligand, chiral ligand and deionized water according to a second preset mass ratio, and reacting under a second preset condition to obtain a core-shell structure metal organic framework chiral material.

[0042] In this embodiment, SiO2 is used as the core, and MOFs are used as the shell to prepare the core-shell structure metal organic framework chiral material MOF@SiO2, which can form spherical particles with a particle size of 5-10 μm, and can solve the defects such as poor column efficiency, high back pressure and poor peak shape of CMOFs as the liquid chromatography column. However, due to the high specific surface area and surface area of silicon dioxide, the surface of silicon dioxide is chemically inert, and the interface compatibility of silicon dioxide and metal organic framework is poor during the synthesis of metal organic framework, it is difficult to form stable chemical bonds or interface bonding, resulting in poor stability of the prepared core-shell structure.

[0043] In order to improve the stability of the core-shell structure, in the embodiment, the dopamine hydrochloride is dissolved in the Tris-HCl buffer solution with weak alkaline, and then reacts with the silicon dioxide. The dopamine hydrochloride contains rich amino and phenolic hydroxyl functional groups, which can be used for surface modification of the silicon dioxide to form a stable polydopamine active layer on the surface of the silicon dioxide, and obtain the polydopamine modified silicon dioxide (SiO2-PDA). The polydopamine modified silicon dioxide is mixed with the metal ion compound, the alkaline adjusting agent, the organic ligand, the chiral ligand and the deionized water, and then reacts to form the metal organic framework in situ on the polydopamine modified silicon dioxide, so that the chiral material with stable performance and core-shell structure can be obtained.

[0044] The method has the advantages of simple and rapid preparation process, no use of organic solvents such as toluene, environmental friendly characteristics, wide source of raw materials, low price, low production cost, high column efficiency, low column pressure (less than 5 MPa) and high separation degree of the chiral material used as the chiral stationary phase when separating various racemic chiral compounds.

[0045] In an example embodiment, the first preset mass ratio is 1:14.20-20.35.

[0046] In the embodiment, the amount of dopamine hydrochloride and silicon dioxide needs to be controlled. If the amount of dopamine hydrochloride is too low, the expected effect cannot be achieved, which affects the bonding strength between the polydopamine modified silicon dioxide and the metal organic framework. If the amount of dopamine hydrochloride is too high, the thickness of the polydopamine coating formed on the surface of the silicon dioxide is not uniform, which also affects the spherical regularity of the spherical particles of the core-shell structure. For example, the first preset mass ratio can be 1:14.20, 1:15.78, 1:16.19, 1:18.32, 1:20.35.

[0047] In an example embodiment, the second preset mass ratio is 3.0-8.0:1.5-6.5:1:1.0-4.0:1.0-4.0.

[0048] The metal organic framework has high porosity and specific surface area. In the embodiment, the ratio of the polydopamine modified silicon dioxide and other raw materials needs to be controlled, which can adjust the structural integrity, porosity and specific surface area of the metal organic framework in the core-shell structure, and improve the separation effect of the product on the racemic chiral compounds. For example, the second preset mass ratio can be 3.0:1.5:1:1.0:1.0, 5.0:2.1:1:1.0:1.6-2.2, 6.5:3.0:1:3.5:3.0, 8.0:6.5:1:4.0:4.0.

[0049] In an exemplary embodiment, the metal ion compound comprises one or more of zinc nitrate hexahydrate, zinc chloride, zinc acetate;

[0050] The basicity regulator comprises one or more of anhydrous sodium carbonate, triethylamine;

[0051] The organic ligand comprises one or more of 4,4'-bipyridine, terephthalic acid, 2-methylimidazole;

[0052] The chiral ligand comprises D-camphoric acid.

[0053] In an exemplary embodiment, the first preset condition comprises:

[0054] The reaction is carried out at a temperature of 20-30°C for 16-24h.

[0055] In this embodiment, the reaction conditions of dopamine hydrochloride and silicon dioxide are mild, and the self-polymerization of dopamine can be realized at room temperature. The reaction conditions are mild and the operation is simple.

[0056] Exemplarily, in an embodiment, the first preset condition comprises: the reaction is carried out at a temperature of 20°C for 24h.

[0057] In another embodiment, the first preset condition comprises: the reaction is carried out at a temperature of 25°C for 20h.

[0058] In another embodiment, the first preset condition comprises: the reaction is carried out at a temperature of 30°C for 16h.

[0059] In an exemplary embodiment, the second preset condition comprises:

[0060] In the first stage, the mixture is stirred at a temperature of 20-30°C for 20-40min;

[0061] In the second stage, the reaction is carried out at a temperature of 115-125°C for 40-55h.

[0062] In this embodiment, by controlling the reaction conditions of dopamine-modified silicon dioxide and other raw materials, the occurrence of side reactions can be reduced and the reaction efficiency can be improved.

[0063] Exemplarily, in an embodiment, the second preset condition comprises: in the first stage, the mixture is stirred at a temperature of 20°C for 40min;

[0064] In the second stage, the reaction is carried out at a temperature of 115°C for 55h.

[0065] In another embodiment, the second preset condition comprises: in the first stage, the mixture is stirred at a temperature of 25°C for 30min;

[0066] In the second stage, the reaction is carried out at a temperature of 120°C for 48h.

[0067] In another embodiment, the second preset condition comprises: a first stage, stirring the mixture at a temperature of 30℃ for 20 min;

[0068] a second stage, reacting at a temperature of 125℃ for 40 h.

[0069] An exemplary embodiment of the present application provides an application of a core-shell structure metal organic framework chiral material. The core-shell structure metal organic framework chiral material according to any one of the above embodiments is used as a chiral stationary phase of a chromatographic column for chiral separation of a racemic compound.

[0070] The chiral stationary phase (CSP) is a key material for separating racemic compounds in chromatography. It realizes the separation of enantiomers by specific interaction with chiral molecules. A racemic compound (Racemic Mixture or Racemate) is a special compound formed by mixing a pair of enantiomers (i.e., two chiral molecules that are mirror images of each other) in equal amounts. Since the enantiomers in the racemic compound have the same physical and chemical properties, a chiral stationary phase is needed to separate the enantiomers by chromatography.

[0071] The Zn-MOF@SiO2 in the present embodiment can be used as a chiral stationary phase of a chromatographic column, and can be used for chiral separation of racemic compounds of 1,1’-binaphthyl, troger base and ibuprofen. The molecular formula of 1,1’-binaphthyl is C 20 H 14 O2, including R-type and S-type enantiomers. The molecular formula of troger base is C 17 H 18 N2; ibuprofen, also known as isobutylphenylpropionic acid, has a molecular formula of C 13 H 18 O2, including R-ibuprofen and S-ibuprofen.

[0072] In the chiral separation of racemic compounds of 1,1’-binaphthyl, troger base and ibuprofen, the mobile phase can be n-hexane: isopropanol = (v / v, 9:1), and the injection amount is 10 μL. The flow rate of the mobile phase affects the residence time of the sample in the chromatographic column and the separation effect. If the flow rate is too fast, the sample may not interact with the stationary phase sufficiently, resulting in incomplete separation. In addition, the flow rate also affects the system pressure. Too high a flow rate may cause the column pressure to be too high, causing damage to the chromatographic column and the instrument. If the flow rate is too slow, the analysis time will be prolonged, which may cause peak broadening and affect the analysis efficiency. Therefore, the flow rate needs to be adjusted according to the type of racemic compound.

[0073] Exemplarily, when the racemic compound is 1,1'-binaphthyl-2-ol, the flow rate of the mobile phase is 0.2-0.6 mL / min. For example, the flow rate is 0.2 mL / min, 0.3 mL / min, 0.5 mL / min, 0.6 mL / min.

[0074] When the racemic compound is troger base, the flow rate of the mobile phase is 0.8-1.2 mL / min. For example, the flow rate is 0.8 mL / min, 1.0 mL / min, 1.2 mL / min, 1.3 mL / min.

[0075] When the racemic compound is ibuprofen, the flow rate of the mobile phase is 0.3-0.7 mL / min. For example, the flow rate is 0.3 mL / min, 0.5 mL / min, 0.6 mL / min, 0.7 mL / min.

[0076] In order to more clearly explain the technical solutions of the present application, the present application lists specific embodiments of the core-shell metal organic framework chiral material.

[0077] Embodiment

[0078] Embodiment 1: A preparation method of a core-shell metal organic framework chiral material Zn-MOF@SiO2-PDA, comprising the following steps:

[0079] (1) Dissolve 123.5 mg of dopamine hydrochloride (DA) in 50 mL of Tris-HCl buffer solution with pH=8.5 to obtain a dopamine hydrochloride solution; then disperse 2.0 g of SiO2 into the dopamine hydrochloride solution, and stand for reaction at room temperature for 20 h to obtain a first product; filter the first product with a G4 sand core funnel to obtain a first solid, wash the first solid with deionized water for 3 times, and vacuum dry at 60°C for 12 h to obtain polydopamine modified SiO2-PDA.

[0080] (2) Mix 0.5 g of SiO2-PDA, 0.44 g of zinc nitrate hexahydrate, 0.10 g of anhydrous sodium carbonate, 0.16 g of 4,4'-dipyridyl, 0.22 g of D-camphoric acid, and 17.3 g of deionized water, stir at room temperature for 30 min, then transfer to a hydrothermal reaction kettle, and react at 120°C for 2 d to obtain a second product; filter the second product with a G4 sand core funnel to obtain a second solid, wash the second solid with deionized water for 3 times, and vacuum dry at 60°C for 12 h to obtain a core-shell metal organic framework chiral material Zn-MOF@SiO2-PDA stationary phase.

[0081] Performance test: The raw material SiO2 and the prepared Zn-MOF@SiO2-PDA in Example 1 were characterized by SEM and FT-IR. The characterization results were consistent with those of Figure 1 、 Figure 2a and Figure 2b As shown. Among them, Figure 1 The horizontal axis is the wave number, the unit is (cm -1 ), the ordinate is absorbance, according to Figure 1 It can be seen that Zn-MOF@SiO2 can be synthesized by the method of Example 1 of this application. Figure 2a and Figure 2b It can be seen that Zn-MOF can grow relatively uniformly on the SiO2 surface.

[0082] Example 2: The main difference between this example and Example 1 is that zinc nitrate hexahydrate in step (2) is replaced by zinc chloride. Specifically, step (2) of this example includes:

[0083] 1.0 g SiO2-PDA, 0.42 g zinc chloride, 0.20 g anhydrous sodium carbonate, 0.32 g 4,4'-bipyridine, 0.44 g D-camphoric acid, and 34.6 g deionized water were mixed, stirred at room temperature for 30 min, then transferred to a hydrothermal reactor and reacted at 120°C for 2 days to obtain a second product; the second product was filtered using a G4 sand core funnel to obtain a second solid, which was washed three times with deionized water and vacuum dried at 60°C for 12 h to obtain a core-shell structure metal organic framework chiral material Zn-MOF@SiO2-PDA stationary phase.

[0084] Example 3: The main difference between this example and Example 1 is that the hexahydrate zinc nitrate in step (2) is replaced by zinc acetate. Specifically, step (2) of this example includes:

[0085] 1.0 g SiO2-PDA, 0.56 g zinc acetate, 0.20 g anhydrous sodium carbonate, 0.32 g 4,4'-bipyridine, 0.44 g D-camphoric acid, and 34.6 g deionized water were mixed, stirred at room temperature for 30 min, then transferred to a hydrothermal reactor and reacted at 120°C for 2 days to obtain a second product; the second product was filtered using a G4 sand core funnel to obtain a second solid, which was washed three times with deionized water and vacuum dried at 60°C for 12 h to obtain a core-shell structure metal organic framework chiral material Zn-MOF@SiO2-PDA stationary phase.

[0086] The Zn-MOF@SiO2-PDA prepared in Example 2 and Example 3 was respectively subjected to FT-IR test, and characteristic absorption peaks of Zn-MOF@SiO2-PDA could be formed, indicating that zinc chloride and zinc acetate were used as the source of zinc ions, and were coordinated with organic ligands to form metal nodes to construct the skeleton structure of MOFs.

[0087] Application Example

[0088] The Zn-MOF@SiO2-PDA prepared in Example 1 was used as a chiral stationary phase, and was packed into a chiral column, and the specific method included the following steps:

[0089] 3g of Zn-MOF@SiO2-PDA was weighed into a beaker, isopropanol (25mL) was added to obtain a Zn-MOF@SiO2 suspension, and then the suspension was quickly poured into a homogenizing tank, and then a methanol solution was used as a displacement liquid to pack the column under a fluid pressure of 40MPa for 30min to obtain a Zn-MOF@SiO2 core-shell HPLC chiral column.

[0090] Chiral column separation performance test: the above Zn-MOF@SiO2 core-shell HPLC chiral column was used to test the chromatographic separation of racemic compounds of 1,1'-binaphthyl, troger base and ibuprofen, and the specific steps were as follows:

[0091] The Zn-MOF@SiO2 core-shell HPLC chiral column was connected to the HPLC, and before testing, n-hexane / isopropanol (v / v, 9:1) was used as the mobile phase to equilibrate the column to the baseline, and then under the conditions of column temperature of 25℃, detection wavelength of 254nm and injection volume of 10μL, the above racemic compounds were subjected to chiral separation. Among them, the flow rate in the test was adjusted according to the different types of racemic compounds, and the following application examples 1-3 were different racemic compounds and the corresponding flow rates, and the test results were as shown in Figures 3-5 , wherein, Figures 3-5 , wherein, the abscissa unit is min, and the ordinate unit is mV, the resolution Rs in each figure was calculated, and the resolution reflected the separation degree between two adjacent chromatographic peaks, and when Rs≥1.5, it was considered to be baseline separation, and the two peaks were completely separated.

[0092] In application example 1, the racemic compound was 1,1'-binaphthyl, and the flow rate was 0.3mL / min, as shown in Figure 3 , the resolution Rs of 1,1'-binaphthyl was 2.03. In application example 2, the racemic compound was troger base, and the flow rate was 1.0mL / min, as shown in Figure 4As shown, the resolution Rs of troger's base is 2.07. In application example 3, the racemic compound is ibuprofen, the flow rate is 0.5 mL / min, and the resolution Rs of ibuprofen is 0.84. Thus, it is illustrated that the Zn-MOF@SiO2core-shell HPLC chiral column has the ability of baseline separation for 1,1'-binaphthyl and troger's base, indicating that it has good chiral separation performance and application prospect.

[0093] In order to test the stability of the Zn-MOF@SiO2core-shell HPLC chiral column, in application example 4, the racemic compound is 1,1'-binaphthyl, and the flow rate is adjusted to 0.5 mL / min. As shown, when the flow rate is increased, the retention time of 1,1'-binaphthyl is greatly shortened, and the resolution is almost unchanged, indicating that Zn-MOF@SiO2has good stability and practicability. Figure 6

[0094] In summary, the Zn-MOF@SiO2column prepared in the present application has the characteristics of low column pressure and high column efficiency, and has good separation performance for a variety of chiral compounds.

[0095] The specific embodiments are only an explanation of the present application, and are not a limitation of the present application, and those skilled in the art can make modifications to the embodiments without creative contribution after reading the present specification, but as long as the modifications are within the scope of the claims of the present application, they are protected by the patent law.​

Claims

1. A method for preparing a core-shell structured metal-organic framework chiral material, characterized in that: The preparation method comprises: mixing dopamine hydrochloride and silicon dioxide in a first preset mass ratio and reacting under first preset conditions to obtain polydopamine-modified silicon dioxide; Dopamine-modified silica, metal ion compound, alkaline regulator, organic ligand, chiral ligand and deionized water in a second preset mass ratio are mixed and reacted under second preset conditions to obtain the core-shell structure metal organic framework chiral material.

2. The method for preparing a core-shell metal organic framework chiral material according to claim 1, characterized in that: The first preset mass ratio is 1:14.20-20.

35.

3. The method for preparing a core-shell metal organic framework chiral material according to claim 1, characterized in that: The second preset mass ratio is 3.0-8.0:1.5-6.5:1:1.0-4.0:1.0-4.

0.

4. The method for preparing a core-shell metal organic framework chiral material according to claim 1, characterized in that: The metal ion compound includes one or more of zinc nitrate hexahydrate, zinc chloride, and zinc acetate; The alkaline regulator includes one or more of anhydrous sodium carbonate, potassium carbonate, and triethylamine; The organic ligand includes one or more of 4,4'-bipyridine and 4-(pyridin-4-yl)pyrimidine; The chiral ligand includes D-camphoric acid.

5. The method for preparing a core-shell metal organic framework chiral material according to claim 1, characterized in that: The first preset condition includes: The reaction was carried out at a temperature of 20-30°C for 16-24 hours.

6. The method for preparing a core-shell metal-organic framework chiral material according to claim 1, characterized in that: The second preset condition includes: In the first stage, the mixture is stirred at a temperature of 20-30°C for 20-40 minutes; In the second stage, the reaction is carried out at a temperature of 115-125°C for 40-55 hours.

7. A core-shell metal-organic framework chiral material, characterized in that: The core-shell structured metal-organic framework chiral material is prepared by the method for preparing a core-shell structured metal-organic framework chiral material according to any one of claims 1 to 6.

8. An application of a core-shell structure metal organic framework chiral material, characterized in that: The core-shell structure metal organic framework chiral material prepared by the preparation method of the core-shell structure metal organic framework chiral material according to any one of claims 1 to 6 or the core-shell structure metal organic framework chiral material according to claim 7 is used as the chiral stationary phase of a chromatographic column for chiral separation of racemic compounds.

9. The use of the core-shell metal organic framework chiral material according to claim 8, characterized in that: The racemic compound includes one or more of 1,1'-binaphthol, trogel's base, and ibuprofen.

10. The use of the core-shell metal organic framework chiral material according to claim 9, characterized in that: When the racemic compound includes 1,1'-binaphthol, the flow rate of the mobile phase is 0.2-0.6 mL / min; When the racemic compound includes Trogel's base, the flow rate of the mobile phase is 0.8-1.2 mL / min; When the racemic compound includes ibuprofen, the flow rate of the mobile phase is 0.3-0.7 mL / min.

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