Method for regulating and controlling dynamic kinetic resolution of spiral polycyclic aromatic hydrocarbon based on inorganic chiral surface and application

Abstract

The invention provides a method for regulating and controlling dynamic kinetic resolution of spiral polycyclic aromatic hydrocarbon based on an inorganic chiral surface and application, and the method comprises the following steps: S1, rotating a substrate clockwise or anticlockwise, and depositing an inorganic material on the substrate by adopting a physical vapor deposition method to obtain an inorganic chiral nano material layer; wherein the contact angle between the inorganic material and N, N-dimethylformamide is less than 22 degrees, and the deposition angle and the normal direction of the substrate form an angle of 86 degrees or 0 degree; s2, dissolving spiral polycyclic aromatic hydrocarbon molecules needing to be split into N, N-dimethylformamide to obtain a solution; then dropwise adding to the surface of the inorganic chiral nano material layer to obtain a sample; and S3, annealing the sample at 40-50 DEG C, and obtaining the homochiral aggregate after the solvent is completely evaporated. The technical scheme provided by the invention is high in controllability, strong in universality and good in stability, and can be used for efficiently preparing chiral compounds with specific configurations.

Description

Technical Field

[0001] This invention relates to the fields of chiral chemistry and materials science, and in particular to a method and its application for the dynamic kinetic separation of helical polycyclic aromatic hydrocarbons based on inorganic chiral surfaces. Background Technology

[0002] Dynamic kinetic resolution (DKR) is one of the key technologies for the efficient preparation of chiral compounds. Its core lies in utilizing the dynamic interconversion between enantiomers to selectively convert one enantiomer in a racemic mixture into another configuration, thereby achieving highly selective resolution. However, for helical polycyclic aromatic hydrocarbons and other compounds with extremely small interconversion energy barriers (such as the 2-nitrogen-doped 4-helicene molecule (2-A [4]H) with an interconversion energy barrier of only 4.25 kcal•mol), the interconversion energy barrier is very small. -1 For compounds containing these compounds, the traditional DKR method faces the following bottlenecks: (1) High difficulty in regulation: rapid interconversion between enantiomers leads to random symmetry breaking, making it impossible to obtain the target chiral configuration product in a directional manner; (2) Material limitations: Existing chiral induction materials are mostly organic ligands or catalysts, which have problems such as poor stability, complicated preparation and high cost; (3) Narrow applicability: Most methods are only applicable to specific types of compounds and cannot be extended to molecules with special topological structures such as helical polycyclic aromatic hydrocarbons.

[0003] While some studies have attempted to regulate the resolution process using chiral surfaces, the construction of atomic-level chiral topologies of inorganic materials and their enantioselective interactions with molecules remain unclear, hindering the achievement of efficient and controllable Dynamic Kinetic Resolution (DKR). Therefore, developing a universal DKR regulation method based on inorganic chiral surfaces is of great significance for advancing chiral chemistry research and industrial applications. Summary of the Invention

[0004] To address the above technical problems, this invention discloses a method and application for controlling the dynamic kinetic separation of helical polycyclic aromatic hydrocarbons based on inorganic chiral surfaces. This method achieves a highly selective, repeatable, and universal DKR method through inorganic chiral surfaces, solving the problems of difficult directional control, narrow applicable material range, and poor stability in the dynamic kinetic separation of helical polycyclic aromatic hydrocarbons in the prior art.

[0005] The technical solution adopted by this invention is as follows: The method for dynamic kinetic resolution of helical polycyclic aromatic hydrocarbons based on inorganic chiral surfaces includes the following steps: Step S1: Rotate the substrate clockwise or counterclockwise, and simultaneously deposit inorganic material on the substrate using physical vapor deposition to obtain an inorganic chiral nanomaterial layer; wherein, the contact angle between the inorganic material and N,N-dimethylformamide is <22°, and the deposition angle is 86° or 0° with respect to the normal direction of the substrate; wherein, a deposition angle of 86° is suitable for the preparation of nanoparticles (CNPs), and a deposition angle of 0° is suitable for the preparation of thin film (CTFs).

[0006] Step S2: Dissolve the helical polycyclic aromatic hydrocarbon molecules to be separated in N,N-dimethylformamide to obtain a solution; drop the solution onto the surface of the inorganic chiral nanomaterial layer to achieve enantioselective adsorption through non-covalent interactions (such as NH…O-Si hydrogen bonds on the SiO2 surface and Au-N coordination bonds on the Au surface) to obtain a sample; Step S3: Anneal the sample at 40~50℃ until the solvent is completely evaporated to obtain a homogeneous chiral aggregate.

[0007] This technical solution utilizes the chiral matching between the atomic-level chiral topology of inorganic chiral surfaces and the helical structure of helical polycyclic aromatic hydrocarbons to achieve selective adsorption through the difference in adsorption energy of enantiomers on the surface (for example, the adsorption energy of M-2-A [4]H on the nLH-Au surface is 0.23 eV lower than that of its enantiomer P type), thereby inducing symmetry breaking. This process realizes multi-level chiral transfer from the macroscopic substrate rotation direction (clockwise / counterclockwise) to atomic-level surface chirality, and then to molecular configuration (M / P). The "guide" molecules of the initial adsorption can induce the subsequent molecules to undergo "follow-up" homochiral stacking, and finally form aggregates with uniform chirality on the macroscopic scale.

[0008] As a further improvement of the present invention, in step S1, the inorganic material is SiO2, Au, titanium oxide, iron oxide or tin oxide.

[0009] As a further improvement of the present invention, in step S1, the rotation speed is 6°•s. -1 .

[0010] As a further improvement of the present invention, in step S1, when the inorganic material is SiO2, the deposition rate is 3 Å / s; when the inorganic material is Au, the deposition rate is 1 Å / s; and when the inorganic material is titanium oxide, iron oxide, or tin oxide, the deposition rate is 0.83 Å / s.

[0011] As a further improvement of the present invention, when the inorganic material is SiO2, the substrate temperature during deposition is 0°C; when the inorganic material is Au, the substrate temperature during deposition is -40°C.

[0012] As a further improvement of the present invention, in step S1, the vacuum degree during the physical vapor deposition process is 10. -7 ~10 -6 torr.

[0013] As a further improvement of the present invention, in step S2, the helical polycyclic aromatic hydrocarbon molecule is 2-A [4]H or 4-nitrogen-doped 4-helicene molecule, and the concentration of the solution is 3-5 mmol / L. Further, the concentration of the solution is 4 mmol / L.

[0014] As a further improvement of the present invention, in step S3, the annealing time is 12 hours.

[0015] As a further improvement of the present invention, in step S1, clockwise rotation induces the formation of P-configuration aggregates; counterclockwise rotation induces the formation of M-configuration aggregates.

[0016] This invention discloses the application of the method described above, which uses inorganic chiral surfaces to regulate the dynamic kinetic resolution of helical polycyclic aromatic hydrocarbons, for the preparation of chiral compounds with specific configurations.

[0017] This invention discloses a method for preparing an inorganic chiral surface, which is also a method for preparing chiral compounds with specific configurations. It employs the method described above for controlling the dynamic kinetic resolution of helical polycyclic aromatic hydrocarbons based on inorganic chiral surfaces.

[0018] As a further improvement of the present invention, the method for preparing the inorganic chiral surface includes: using physical vapor deposition at a vacuum degree of 10... -7 ~10 -6 Under torr conditions, inorganic materials were deposited on the substrate at rates of 3 Å / s (silicon dioxide), 1 Å / s (gold), or 0.83 Å / s (metal oxides), with deposition angles of 86° or 0°, and substrates at 6°•s. -1 The speed of rotation is clockwise or counterclockwise, forming an atomic-level chiral topology with a contact angle of <22° with DMF.

[0019] As a further improvement of the present invention, when the inorganic material is gold, the substrate temperature is controlled at -40°C during the deposition process, forming a structure with ( Chiral step structure of high Miller index crystal planes.

[0020] Compared with the prior art, the beneficial effects of the present invention are as follows: The technical solution of this invention involves preparing inorganic surfaces (such as silica, gold nanoparticles, or thin films) with atomically chiral topologies through physical vapor deposition combined with substrate rotation. Enantioselective adsorption is achieved by utilizing the non-covalent N-inorganic bond interaction between high surface energy materials (DMF contact angle < 22°) and nitrogen-doped helical polycyclic aromatic hydrocarbons. Following the chiral amplification effect of uniform chiral π-π stacking, M- or P-configuration aggregates are directionally generated. This method allows for precise control of the product configuration (M / P) by adjusting the substrate rotation direction, achieving directional controllability and solving the problem of random resolution of compounds with low interconversion energy barriers. The technical solution of this invention has the following advantages: 1) High versatility: Applicable to various nitrogen-doped helical polycyclic aromatic hydrocarbons such as 2-A[4]H and 4-A[4]H, and can be extended to SiO2, Au, TiO x Various inorganic material systems; 2) Good stability and repeatability: Inorganic chiral surfaces have high chemical stability and can be reused, overcoming the defect of easy degradation of organic chiral materials; 3) High efficiency and low cost: No expensive chiral ligands are required, and the physical vapor deposition process is easy to scale up, reducing the cost of preparing chiral compounds; 4) Scientific value: It reveals the matching mechanism between inorganic surface chirality and molecular chirality, and provides an experimental model for understanding the origin of homochirality of pre-biological Earth. Attached Figure Description

[0021] Figure 1 This is a schematic diagram of the method for dynamic kinetic separation of helical polycyclic aromatic hydrocarbons based on inorganic chiral surfaces according to the present invention.

[0022] Figure 2This is the UV-Vis spectrum analysis of the product obtained by regulating the dynamic kinetic resolution (DKR) of 2-A [4]H by silica chiral nanoparticles prepared by physical vapor deposition (PVD) combined with substrate rotation technology in Example 1 of this invention; wherein, a and b are the UV-Vis extinction (EXT) and circular dichroism (CD) spectra characterization results of nLH-silica CNPs and nominal right-handed (nRH) silica chiral nanoparticles. In a, the inset is a scanning electron microscope (SEM) tilted image of nLH-silica CNPs. In b, the inset is: the upper inset is nominal nLH, and the lower inset is a transmission electron microscope (TEM) image of nRH-silica CNPs, with a selected area electron diffraction (SAED) pattern. c is the UV-Vis absorption spectrum (grass green line) and CD spectrum (black line) of 1 mmol / L 2-A [4]H in N,N-dimethylformamide (DMF) solution. In Figure c: The upper inset shows the molecular structure of M-type and P-type 2-A [4]H; the lower inset shows the absorption spectrum magnified 20 times in the wavelength range of 350–400 nm. Figures df show the UV-Vis extinction spectrum, CD spectrum and anisotropic g-factor spectrum of the sample after the DKR process, where the red line is the surface of nLH silica-CNPs and the blue line is the surface of nRH silica-CNPs; In Figure d: SEM tilted image of 2-A [4]H aggregates on the surface of nLH silica-CNPs. In Figure df, the spectra are presented as mean (solid line) and standard deviation (shaded area), and the statistical data are from multiple samples. Scale bar: 100 nm (insets of a, b, and d).

[0023] Figure 3This is the UV-Vis spectrum analysis of the product obtained by regulating the dynamic kinetic resolution (DKR) of 2-A[4]H by gold chiral nanoparticles prepared by physical vapor deposition (PVD) combined with substrate rotation technology in Example 2 of this invention. Among them, a is the extinction spectrum of nLH-Au CNPs and nRH-Au CNPs, b is the CD spectrum characterization of nLH-Au CNPs and nRH-Au CNPs, and c is the X-ray diffraction (XRD) pattern of nLH Au CNPs; in the inset of b, the upper inset is the nominal left-handed nLH-Au CNPs, and the lower inset is the SEM tilt image of the nominal nRH Au CNPs. d is the extinction spectrum of 2-A[4]H aggregates on the surface of Au CNPs, e is the CD spectrum of 2-A[4]H aggregates on the surface of Au CNPs, and f is the anisotropic g-factor spectrum of 2-A[4]H aggregates on the surface of Au CNPs; where the inset in d is a SEM tilted image of nLH Au CNPs 2-A[4]H aggregates. In df, the spectra are presented as mean (solid line) and standard deviation (shaded area), and the statistical data are from multiple samples. Scale bar: 100 nm (insets in b and d).

[0024] Figure 4 The images are UV-Vis spectra of the products obtained by controlling the dynamic kinetic resolution of 2-A[4]H using chiral thin films (CTFs) prepared with different inorganic materials in Examples 3-7 of this invention. Among them, the three images in group a are silicon dioxide, the three images in group b are titanium oxide, the three images in group c are iron oxide, the three images in group d are tin oxide, and the three images in group e are gold; aI, bI, cI, dI, and eI are the extinction (EXT) spectra of 2-A[4]H aggregates on the surfaces of each material-free material (silicon dioxide, titanium oxide, iron oxide, tin oxide, and gold), a-II, b-II, c-II, d-II, and e-II are the circular dichroism (CD) spectra of 2-A[4]H aggregates on the surfaces of each material-free material, and a-III, b-III, c-III, d-III, and e-III are the anisotropic g-factor spectra of each material-free material. The insets in aI, bI, cI, dI, and eI are contact angle photographs of N,N-dimethylformamide (DMF) on different inorganic CTFs surfaces. In ac, the spectra are presented as mean (solid line) and standard deviation (shaded area), with statistics from multiple samples.

[0025] Figure 5This is the UV-Vis spectrum analysis of the product obtained in Comparative Example 1 of the present invention. In the spectrum, a is the extinction (EXT) spectrum, and b is the circular dichroism (CD) spectrum; the inset in a is a photograph of the contact angle of N,N-dimethylformamide (DMF) on the Ag CTFs surface. Detailed Implementation

[0026] The preferred embodiments of the present invention will be described in further detail below.

[0027] A method for dynamic kinetic resolution of helical polycyclic aromatic hydrocarbons based on inorganic chiral surfaces includes the following steps: (1) Preparation of inorganic chiral surfaces Inorganic chiral surfaces with atomic-level chiral topologies were prepared using physical vapor deposition (PVD) combined with substrate rotation technology, specifically including: Deposition system: Electron beam evaporation physical vapor deposition equipment, with vacuum level controlled at 10. -7 ~10 -6 torr.

[0028] Material selection: High surface energy inorganic materials are selected, including but not limited to silicon dioxide (SiO2), gold (Au), and titanium oxide (TiO2). x ), iron oxide (Fe x O y ), tin oxide (SnO x The contact angle between the substance and N,N-dimethylformamide (DMF) must be <22°.

[0029] Chiral regulation parameters: Deposition angle α: 86° to the substrate normal (suitable for nanoparticle CNPs preparation) or 0° (suitable for thin film CTFs preparation); Substrate rotation: Clockwise (CW) rotation generates a nominal right-handed (nRH) surface, and counterclockwise (CCW) rotation generates a nominal left-handed (nLH) surface, at a rotation rate of 6°•s. -1 ; Deposition rates: 3 Å / s for SiO2, 1 Å / s for Au, and 0.83 Å / s for metal oxides; Substrate temperature: 0℃ during SiO2 deposition and -40℃ during Au deposition.

[0030] (2) Dynamic kinetic resolution of helical polycyclic aromatic hydrocarbons: Reactant preparation: Helical polycyclic aromatic hydrocarbon molecules (such as 2-A[4]H, 4-nitrogen-doped 4-helicene molecules (4-A[4]H)) were dissolved in DMF to prepare a solution with a concentration of 4 mmol•L. -1 The solution.

[0031] Enantioselective adsorption: Take 60 μL of the above solution and drop it onto the inorganic chiral surface prepared in step (1). Enantioselective adsorption is achieved through non-covalent interactions (such as NH…O-Si hydrogen bonds on the SiO2 surface and Au-N coordination bonds on the Au surface).

[0032] Chiral amplification and aggregate formation: The sample was annealed at 45°C overnight. After solvent evaporation, homogeneous chiral π-π stacking occurred through the "general-and-soldiers" mechanism, forming M-configuration aggregates on the nLH surface and P-configuration aggregates on the RH surface.

[0033] Product characterization: Circular dichroism (CD) analysis showed that the absolute value of the anisotropy g-factor of the target product was 0.003~0.006, indicating successful separation.

[0034] The principle of the method of the present invention is illustrated below using Au as the deposition material and 2-A [4] H as the helical polycyclic aromatic hydrocarbon molecule. Figure 1 The diagram shows a deterministic dynamical rendition (DKR) of 2-A[4]H based on an atomically chiral inorganic surface, illustrating the process achieved through directional symmetry breaking and "commander-soldier" chiral amplification. Figure 1 In the 'a', the molecular structure of the M-type and P-type isomers of 2-A [4] H isoform. Figure 1 In the figure, b represents nRH-AuCNPs obtained by CW spin deposition on the substrate, and 2-A [4]H molecules aggregate on its surface to form a pure chiral P-type isomer supramolecular film. Figure 1 In the figure, c represents nLH-AuCNPs obtained by CCW spin deposition on the substrate, and 2-A [4] H molecules aggregate on its surface to form a pure chiral M-type isomer supramolecular film. Among them, through the atomic-level inorganic helical structure (II and III) as the medium, chirality is transferred from the macroscopic level (I: clockwise or counterclockwise rotation of the substrate) to the molecular level (IV). Figure 1 The realization process of symmetry breaking of d for 2-A [4]H: M-type 2-A [4]H on the high-index surface of gold ( Enantiomers preferentially adsorb at the nLH step site of ) and then chiral amplification is carried out through pure chiral π-π stacking, eventually generating pure chiral M-type 2-A[4] H aggregates.

[0035] The following description uses specific examples to illustrate the point.

[0036] Example 1 2-A[4]H resolution based on silica chiral nanoparticles (CNPs) includes the following steps: (1) Preparation of nLH-SiO2CNPs: Substrate: Sapphire (1.5 × 1.5 cm²). SiO2 was deposited on the substrate using an electron beam evaporation physical vapor deposition apparatus.

[0037] Deposition parameters: Vacuum degree 10 -6 torr, deposition angle α = 86°, substrate rotated counterclockwise by CCW at a rotation rate of 6°•s -1 With a deposition rate of 3 Å / s, a substrate temperature of 0℃, and 20 deposition cycles, CNPs with a pitch of P=6.5 nm and a height of H=130 nm were obtained.

[0038] The deposited nLH-silica CNPs and nominally right-handed (nRH) silica chiral nanoparticles (7.8 nm helical spacing, 156 nm height) were characterized by UV-Vis (a) extinction (EXT) and (b) circular dichroism (CD) spectra as follows: Figure 2 a and Figure 2 As shown in b, SiO2 with an atomic-level chiral topological structure is obtained.

[0039] (2) DKR process: Take 60 μL of 4 mmol•L -1 A DMF solution of 2-A [4] H was dropped onto the surface of the above CNPs.

[0040] Anneal at 45℃ for 12 h until the solvent is completely evaporated.

[0041] like Figure 2 As shown in c, the UV-Vis absorption spectrum of a 1 mmol / L 2-A [4]H N,N-dimethylformamide (DMF) solution is shown. Figure 2 c) grass green line) and CD spectrum ( Figure 2 As can be seen from the black line in c, 2-A [4]H contains both M-type and P-type structures. 60 μL of a DMF solution containing 4 mmol / L 2-A [4]H was dropped onto the surface of the chiral silica nanoparticles, followed by annealing at 45 °C to evaporate the solvent. The final sample was analyzed by UV-Vis spectroscopy as follows: Figure 2 d~ Figure 2 As shown in f, by characterizing the extinction spectrum, CD spectrum and anisotropic g-factor spectrum of the 2-A [4]H aggregates formed on the surface of nLH (red line) and nRH (blue line) silica-CNPs, it can be seen that this step achieves the aggregation of 2-A [4]H.

[0042] The final sample CD spectrum showed a positive signal (M configuration) at 340~380 nm, and the g factor was 0.006 at 378 nm. XRD detected the characteristic diffraction peak of 2-A [4] H, confirming the formation of homogeneous chiral aggregates.

[0043] In the above DKR process, the P:M configuration of 2-A [4] H is 1:1. During the splitting process, more M configurations are preferentially generated on the surface of nLH CNP through dynamic splitting, and then P is converted into M configurations through the "general-soldier" effect.

[0044] Example 2 2-A[4]H resolution based on gold chiral nanoparticles (CNPs) includes the following steps: (1) Preparation of nRH-Au CNPs: Substrate: Silicon wafer. Au is deposited on the substrate using an electron beam evaporation physical vapor deposition (EBV) system.

[0045] Deposition parameters: Vacuum degree 10 -7 torr, deposition angle α = 86°, substrate rotated clockwise (CW) at a rotation rate of 6°•s -1 At a deposition rate of 1 Å / s and a substrate temperature of -40℃, CNPs with P=8.4 nm and H=84 nm were obtained after 10 deposition cycles.

[0046] (2) DKR process: Same as in Example 1.

[0047] The obtained sample was subjected to ultraviolet-visible spectroscopy, and the results are as follows: Figure 3 As shown, this embodiment achieves the aggregation of 2-A [4]H. The CD spectrum of the product obtained in this embodiment shows a negative signal (P configuration) at 340~380 nm, and the g factor is -0.003. High-resolution TEM observed Au ( Chiral step structure.

[0048] Example 3 2-A H separation based on titanium oxide chiral thin films (CTFs) [4] includes the following steps: (1) nLH-TiO x CTFs preparation: Substrate: Silicon wafer. TiO2 was deposited on the substrate using electron beam evaporation physical vapor deposition equipment. x .

[0049] Deposition parameters: Vacuum degree 10 -6 torr, deposition angle α=0°, substrate rotated counterclockwise (CCW) at a rotation rate of 6°•s. -1The deposition rate was 0.83 Å / s, and the thickness was 50 nm.

[0050] (2) DKR procedure: using 4 mmol•L -1 The DMF solution of 2-A [4] H was used, and the rest was the same as in Example 1.

[0051] The obtained samples were tested, and CD spectroscopy showed characteristic signals of the M configuration with a g factor of 0.005. XPS confirmed the interaction between N and Ti.

[0052] Example 4 Based on Example 3, the difference in this example is that a chiral silicon dioxide film is deposited on the substrate.

[0053] Example 5 Based on Example 3, the difference in this example is that a chiral iron oxide film is deposited on the substrate.

[0054] Example 6 Based on Example 3, the difference in this example is that a chiral tin oxide film is deposited on the substrate.

[0055] Example 7 Based on Example 3, the difference in this example is that an Au chiral film is deposited on the substrate.

[0056] The performance test results of the products obtained in Examples 3 to 7 are as follows: Figure 4 As shown. Figure 4 In the figure, a to e represent the characterization results of 2-A[4]H aggregates on the chiral thin film surfaces of silica, titanium oxide, iron oxide, tin oxide, and gold, respectively. The ultraviolet-visible extinction (EXT), circular dichroism (CD), and anisotropic g-factor spectra of 2-A[4]H aggregates on the surfaces of each material (silica, titanium oxide, iron oxide, tin oxide, and gold) show that the CD spectrum exhibits the characteristic signal of the M configuration, and the g-factor is in the range of 0.003 to 0.006, indicating that the separation was successfully achieved.

[0057] Comparative Example 1 A comparative experiment was conducted using silver, a material with low surface energy, including the following steps: (1) Preparation of silver (Ag) CTFs: Substrate: Silicon wafer.

[0058] The deposition parameters were the same as in Example 3, and the material was Ag.

[0059] (2) DKR process: Same as in Example 1.

[0060] The UV-Vis spectrum of the product obtained in Comparative Example 1 is shown below. Figure 5 As shown, the contact angle between the Ag surface and DMF is 46.3°. The obtained sample was tested, and the CD spectrum showed no obvious chiral signal, indicating that DKR could not be achieved.

[0061] The above description, in conjunction with specific preferred embodiments, provides a further detailed explanation of the present invention. It should not be construed that the specific implementation of the present invention is limited to these descriptions. For those skilled in the art, various simple deductions or substitutions can be made without departing from the concept of the present invention, and all such modifications and substitutions should be considered within the scope of protection of the present invention.

Claims

1. A method for dynamic kinetic resolution of helical polycyclic aromatic hydrocarbons based on inorganic chiral surfaces, characterized in that: Includes the following steps: Step S1: Rotate the substrate clockwise or counterclockwise, and simultaneously deposit inorganic materials on the substrate using physical vapor deposition to obtain an inorganic chiral nanomaterial layer; wherein, the contact angle between the inorganic material and N,N-dimethylformamide is <22°, and the deposition angle is 86° or 0° with respect to the normal direction of the substrate. Step S2: Dissolve the helical polycyclic aromatic hydrocarbon molecules to be separated in N,N-dimethylformamide to obtain a solution; add the solution dropwise onto the surface of the inorganic chiral nanomaterial layer to obtain a sample; Step S3: Anneal the sample at 40~50℃ until the solvent is completely evaporated to obtain a homogeneous chiral aggregate.

2. The method for dynamic kinetic resolution of helical polycyclic aromatic hydrocarbons based on inorganic chiral surfaces according to claim 1, characterized in that: Step S1, the inorganic material is SiO2, Au, titanium oxide, iron oxide, or tin oxide; the rotation speed is 6°•s. -1 .

3. The method for dynamic kinetic separation of helical polycyclic aromatic hydrocarbons based on inorganic chiral surfaces according to claim 2, characterized in that: In step S1, when the inorganic material is SiO2, the deposition rate is 3 Å / s and the substrate temperature is 0℃; when the inorganic material is Au, the deposition rate is 1 Å / s and the substrate temperature is -40℃; when the inorganic material is titanium oxide, iron oxide or tin oxide, the deposition rate is 0.83 Å / s.

4. The method for dynamic kinetic separation of helical polycyclic aromatic hydrocarbons based on inorganic chiral surfaces according to claim 3, characterized in that: In step S1, the vacuum level during the physical vapor deposition process is 10. -7 ~10 -6 torr.

5. The method for dynamic kinetic resolution of helical polycyclic aromatic hydrocarbons based on inorganic chiral surfaces according to claim 1, characterized in that: In step S2, the helical polycyclic aromatic hydrocarbon molecule is 2-A [4] H or 4-nitrogen-doped 4-helicene molecule, and the concentration of the solution is 3-5 mmol / L.

6. The method for dynamic kinetic resolution of helical polycyclic aromatic hydrocarbons based on inorganic chiral surfaces according to claim 1, characterized in that: In step S3, the annealing time is 12 hours.

7. The method for dynamic kinetic resolution of helical polycyclic aromatic hydrocarbons based on inorganic chiral surfaces according to any one of claims 1 to 6, characterized in that: In step S1, when the substrate is rotated clockwise, P-configuration aggregates are induced to form; when the substrate is rotated counterclockwise, M-configuration aggregates are induced to form.

8. The application of the method for dynamic kinetic resolution of helical polycyclic aromatic hydrocarbons based on inorganic chiral surfaces as described in any one of claims 1 to 7, characterized in that: Used to prepare chiral compounds with specific configurations.

9. A method for preparing an inorganic chiral surface, characterized in that: The method for dynamic kinetic separation of helical polycyclic aromatic hydrocarbons based on inorganic chiral surfaces as described in any one of claims 1 to 7 is adopted.

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