Circularly polarized excimeric light-emitting molecules, light-emitting materials, and methods of making and using the same

Abstract

This invention discloses a circularly polarized excimer luminescent molecule, luminescent material, and their preparation methods and applications. The circularly polarized excimer luminescent molecule of this invention has the structural formula shown in formula (I) or formula (II): In formulas (I) and (II), R is a polycyclic aromatic hydrocarbon group containing a π-conjugated system. Compared to single-module and dual-module designs, the circularly polarized excimer luminescent molecule obtained by the helical self-locking molecular design of this invention exhibits stable luminescence, independent of both solution concentration and solvent type; and using a helical self-locking strategy, a chiral pyrene ring was successfully constructed using pyrene as a model, exhibiting stable excimer emission and CPEE performance in solution and various assemblies.

Description

Technical Field

[0001] This invention belongs to the interdisciplinary field of optical materials and chiral materials, specifically relating to a method for preparing highly stable circularly polarized exciton-associated light-emitting molecules and aggregate materials. The circularly polarized exciton-associated light-emitting molecules involved have potential applications in constructing stable light-emitting devices. Background Technology

[0002] Circularly polarized luminescence (CPL) is an excited-state property of luminescent chiral substances and an important chiral function with wide applications in light-emitting devices, 3D displays, information storage, biological probes, and the synthesis of chiral substances. CPL is a unique chiral optical property that can be used to acquire and understand the excited-state chiral information of a system. It has broad applications in 3D displays, intelligent encryption, high-density information storage, circularly polarized light-emitting devices and spintronic devices, asymmetric catalysis, and biosensing. Therefore, in recent years, it has become a cutting-edge interdisciplinary research area in chemistry, chirality, physics, optics, materials science, and biology. Currently, common circularly polarized luminescent materials mainly include systems such as small organic molecules, polymers, metal complexes, metal clusters, supramolecular assemblies, and liquid crystals. The construction systems and strategies for circularly polarized luminescent materials have made significant progress, and it is now possible to achieve circularly polarized luminescence properties with various emission colors and multiple stimulus responses. Starting from chiral luminescent molecules, constructing circularly polarized luminescent chiral functional materials, and ultimately developing them for practical circularly polarized light-emitting devices, supramolecular aggregates are an essential step. However, for most molecular systems, different preparation methods for luminescent materials will result in aggregates of varying degrees, and their emission colors often exhibit unpredictable changes. For aggregation-induced quenching (AIEgens) molecules, although AIEgens can be used to address the ACQ effect, neither ACQ dyes nor AIEgens aggregate systems can avoid changes in luminescent group color, and their luminescence efficiency often continuously decreases. Therefore, rationally designing chiral molecular systems with high environmental tolerance for luminescence and constructing highly stable circularly polarized luminescent functional materials remains a significant challenge.

[0003] Since excimer luminescence is a characteristic of binary dimers closely related to excited-state processes, circularly polarized luminescence based on excimers can be achieved by appropriately introducing chiral units. Therefore, it has attracted considerable attention in the field of circularly polarized luminescence. Currently, most excimer-based circularly polarized luminescent active materials typically modulate the circularly polarized luminescence properties of excimers by adjusting the binding mode between excimer-forming luminescent units and chiral units. However, it is worth noting that, whether in the molecular or aggregated state, the molecular conformation is easily affected by the external environment and assembly method, leading to varying degrees of excimer formation. Therefore, it is difficult to obtain stable excimer luminescence colors. For example, Cheng Yixiang's research group integrated luminescent 1,8-naphthalimide with chiral cyclohexanediamine via covalent bonds. However, the excimer luminescence efficiency of the 1,8-naphthalimide luminescent group is heavily dependent on the THF / H2O solvent ratio; when the H2O content reaches 80%, the excimer fluorescence is significantly quenched. Furthermore, the aggregation process is accompanied by a reversal of the circularly polarized luminescence signal. Liu Minghua's research group subsequently reported the synthesis of a series of V-shaped luminescent molecules containing chiral cyclohexanediamine and pyrene luminescent groups. Interestingly, by changing the length of the linker units, the rigidity and flexibility of the molecular framework can be altered, thus exhibiting excimer circularly polarized luminescence properties with varying degrees of luminescence color. Among them, the V-shaped molecule with a rigid symmetry structure formed the strongest intramolecular excimer and exhibited the strongest circularly polarized luminescence. However, by employing a supramolecular self-assembly strategy to enhance chiral transfer within the assembly, the circularly polarized luminescence asymmetry factor was significantly improved. Nevertheless, all molecules still exhibited uncontrollable changes in luminescence color and a decrease in luminescence efficiency. Therefore, a good solution for constructing highly stable circularly polarized excimer luminescent materials remains lacking, especially a universally applicable rational molecular design scheme. Summary of the Invention

[0004] The purpose of this invention is to provide circularly polarized excimer luminescent molecules, luminescent materials, and their preparation methods and applications. These excimer circularly polarized luminescent materials are universal and stable. This invention will develop a series of chiral cyclohexanediamine-based excimer circularly polarized luminescent molecules by employing a helical self-locking molecular design strategy. By helically confining the molecular backbone, the conformational stability of the molecules is enhanced, achieving highly efficient molecular excimer luminescence and chiral transfer. Furthermore, the luminescence properties are highly resistant to environmental factors such as solvent temperature and assembly conditions, thereby obtaining highly stable circularly polarized excimer luminescence properties.

[0005] In a first aspect, the present invention provides a circularly polarized excito-association luminescent molecule, the structural formula of which is shown in formula (I) or formula (II):

[0006]

[0007] In formulas (I) and (II), R is a polycyclic aromatic hydrocarbon group containing a π-conjugated system.

[0008] In the above-mentioned circularly polarized excimer luminescent molecules, R is any one of the groups shown in Formulas 1-6 below:

[0009]

[0010]

[0011] Secondly, the present invention provides a method for preparing the circularly polarized excimer luminescent molecule, comprising the following steps: in a solvent, a chiral 1,2-cyclohexanediamine undergoes a dynamic covalent reaction of an imine bond with a dialdehyde derivative of a polycyclic aromatic hydrocarbon to obtain the circularly polarized excimer luminescent molecule.

[0012] In the above-mentioned method for preparing circularly polarized excimer luminescent molecules, the solvent may be at least one of N,N-dimethylformamide, water, chloroform, tetrahydrofuran, toluene, and mesitylene.

[0013] The chiral 1,2-cyclohexanediamine may be (1R,2R)-1,2-cyclohexanediamine or (1S,2S)-1,2-cyclohexanediamine;

[0014] The dialdehyde derivative of the polycyclic aromatic hydrocarbon can be pyrene-dicarboxaldehyde, naphthalene-dicarboxaldehyde, anthracene-dicarboxaldehyde, or perylene-dicarboxaldehyde; specifically, pyrene-dicarboxaldehyde can be pyrene-1,6-dicarboxaldehyde.

[0015] The molar ratio of the chiral 1,2-cyclohexanediamine to the dialdehyde derivative of the polycyclic aromatic hydrocarbon can be 1.05:1;

[0016] The reaction temperature for the dynamic covalent reaction of the imine bond can be 15–30°C, such as 25°C, and the reaction time can be 3–7 days, such as 7 days.

[0017] The method further includes the following steps after the reaction is completed: filtering the reactants and recrystallizing them using CHCl3 and MeOH to obtain the target product.

[0018] Thirdly, the present invention provides a circularly polarized excimer luminescent material, which is a supramolecular assembly of the circularly polarized excimer luminescent molecules.

[0019] Fourthly, the present invention provides a method for preparing the circularly polarized excimer luminescent material, comprising the following steps:

[0020] The circularly polarized excimer luminescent molecules are added to an organic solvent, heated until dissolved, then a poor solvent is added, cooled, and the precipitated product is collected to obtain the circularly polarized excimer luminescent material.

[0021] In the above-mentioned method for preparing circularly polarized excimer luminescent materials, the organic solvent may be at least one of N,N-dimethylformamide, water, chloroform, tetrahydrofuran, toluene, and mesitylene.

[0022] The ratio of the circularly polarized excimer luminescent molecule to the organic solvent can be 1 mmol: (0.5–3) mL, such as 1 mmol R CP-Im: 3ml DMF, 1mmol R CP-Im: 1.5ml DMF, 1mmol R CP-Im: 0.5 ml CHCl3, 1 mmol R CP-Im: 0.25 ml CHCl3;

[0023] The unsuitable solvent may be acetonitrile, water, n-hexane, methanol, or ethanol;

[0024] The volume ratio of the organic solvent to the undesirable solvent can be 1:(0.3-3), such as 1:0.3 (3ml DMF: 1ml H2O) or 1:3 (1ml CHCl3 solvent: 3ml acetonitrile).

[0025] In this invention, the FL excitation wavelength of the circularly polarized excimer luminescent molecule or the circularly polarized excimer luminescent material is 360 nm, and the CPL is 360 nm; it exhibits stable excimer emission and CPEE performance in solution and various assemblies.

[0026] Fifthly, the present invention provides the application of the circularly polarized excimer luminescent molecule or the circularly polarized excimer luminescent material in circularly polarized luminescence.

[0027] In a sixth aspect, the present invention provides an application device made of the aforementioned circularly polarized excimer light-emitting material.

[0028] Furthermore, the application device may be at least one of anti-counterfeiting devices, 3D displays, OLEDs, chiral separation membranes, and optoelectronic devices.

[0029] The present invention has the following beneficial effects:

[0030] (1) The chiral motif provided by the present invention is based on cyclohexanediamine of RR / SS as the main chiral source.

[0031] (2) In this invention, π-conjugated molecules containing diformyl groups are selected as luminescent units. Through dynamic covalent reactions of imine bonds, helical self-locking luminescent molecules are synthesized with high efficiency and high yield in an appropriate reaction solvent system.

[0032] (3) This invention proposes a molecular design strategy of helical self-locking to synthesize a strictly limited chiral luminescent pyrene ring skeleton, thereby achieving highly efficient molecular excimer luminescence and highly stable circularly polarized luminescence.

[0033] (4) This invention also synthesizes chiral dimers and chiral single-element molecules based on conventional molecular design concepts. Through systematic property comparison and analysis, the effectiveness of the helical self-locking molecular design strategy is verified.

[0034] This invention further verifies that the luminescent molecules designed with helical self-locking exhibit stable excimer luminescence properties by comparing the luminescent properties of luminescent molecules designed with single-atom, dual-atom, and helical self-locking motifs. The specific analysis is as follows:

[0035] (a) Single-unit design: Chiral units and luminescent units that readily form excimers are integrated together via covalent or non-covalent bonds. This method is suitable for forming intermolecular excimers. Therefore, the efficiency of excimer formation is highly dependent on factors such as concentration and solvent environment, and the luminescence properties are extremely unstable. Moreover, in the assembly, the luminescence color also changes continuously with the degree of aggregation and the assembly structure.

[0036] (b) Dual-unit design: Two luminescent units that readily form excimers are simultaneously linked together via covalent bonds on the same chiral unit. This method is highly favorable for intramolecular excimer luminescence. Compared to intermolecular excimer luminescence, the luminescence efficiency and stability of the excimer are greatly improved, resulting in a significant increase in luminescence efficiency. Moreover, since both units reside on the same chiral unit, chiral transfer is also enhanced. Therefore, the luminescence performance of circularly polarized excimers is often significantly improved.

[0037] (c) Helical self-locking molecular design: By confining the molecular skeleton with helices, the stability of the molecular structure is enhanced, thereby obtaining a stable excimer luminescence property.

[0038] Experimental results show that, compared to single-element and dual-element designs, the circularly polarized excimer luminescent molecules obtained by the helical self-locking molecular design of this invention exhibit stable luminescence, independent of both solution concentration and solvent type. Furthermore, this invention employs a helical self-locking strategy to successfully construct chiral pyrene rings modeled after pyrene, which demonstrate stable excimer emission and CPEE performance in both solutions and various assemblies. In other words, the helical self-locking strategy proposed in this invention is an effective means of creating stable luminescent materials that are independent of construction methods and aggregation structures. Attached Figure Description

[0039] Figure 1 The one prepared in Example 1 of this invention R The hydrogen NMR spectrum of CP-Im.

[0040] Figure 2 The one prepared in Example 1 of this invention R Mass spectrometry of CP-Im.

[0041] Figure 3 The one prepared in Example 1 of this invention S The hydrogen NMR spectrum of CP-Im.

[0042] Figure 4 The one prepared in Example 1 of this invention S Mass spectrometry of CP-Im.

[0043] Figure 5 For different concentrations in Example 1 of the present invention, R FL spectrum (a) and CPL spectrum (b) of CP-Im molecular solution.

[0044] Figure 6 For the same concentration in Example 1 of this invention, different solvents... R FL spectrum (a) and CPL spectrum (b) of CP-Im molecular solution.

[0045] Figure 7 In Embodiment 1 of the present invention R FL spectrum (a) and CPL spectrum (b) of CP-Im assemblies in a mixed solvent (DMF / H2O).

[0046] Figure 8 In Embodiment 1 of the present invention R FL spectrum (a) and CPL spectrum (b) of CP-Im assembled in a mixed solvent (TCM / ACN).

[0047] Figure 9 The one prepared in Comparative Example 1 of this invention S The 1H NMR spectrum of MP-Im.

[0048] Figure 10 The one prepared in Comparative Example 1 of this invention S Mass spectrometry of MP-Im.

[0049] Figure 11 The product prepared in Comparative Example 2 of this invention R The hydrogen NMR spectrum of DP-Im.

[0050] Figure 12 The product prepared in Comparative Example 2 of this invention R Mass spectrometry of DP-Im.

[0051] Figure 13 For different concentrations in Comparative Example 1 of this invention, S FL spectrum (a) and CPL spectrum (b) of MP-Im molecular solution.

[0052] Figure 14 For different concentrations in Comparative Example 2 of this invention, R FL spectrum (a) and CPL spectrum (b) of DP-Im molecular solution.

[0053] Figure 15 For the same concentration, Comparative Example 1 of the present invention S MP-Im molecule (a) and Comparative Example 2 of the present invention R FL spectra of DP-Im molecules (b) in solvents with different polarities.

[0054] Figure 16 As in Comparative Example 1 of the present invention S FL (a) and CPL spectra (b) of the MP-Im assembly.

[0055] Figure 17 As in Comparative Example 2 of the present invention R FL(a) and CPL spectra (b) of the DP-Im assembly. Detailed Implementation

[0056] The present invention will now be described in further detail with reference to specific embodiments. The given embodiments are merely illustrative of the invention and not intended to limit its scope. The embodiments provided below can serve as a guide for further improvements by those skilled in the art and do not constitute a limitation on the invention in any way.

[0057] Unless otherwise specified, the methods used in the following embodiments are conventional methods, performed according to the techniques or conditions described in the literature in this field or according to the product instructions. Unless otherwise specified, the materials and reagents used in the following embodiments are commercially available.

[0058] Example 1

[0059] (1) Preparation of helical self-locking molecules

[0060] 239.8 mg (1R,2R)-1,2-cyclohexanediamine (2.1 mmol) and 516.54 mg pyrene-1,6-dicarboxaldehyde (2 mmol) were completely dissolved in 200 ml of DMF and stirred at room temperature (25 °C) for 7 days. During the stirring process, a product precipitated. After the reaction was completed, the reactants were directly filtered, and then recrystallized three times with CHCl3 and MeOH to finally obtain the target product. R CP-Im. The product is a pale yellow solid with a yield of 60%. R The structural characterization of CP-Im is as follows: Figure 1 and Figure 2 As shown.

[0061]

[0062] S Synthesis method of CP-Im and R CP-Im is the same, except that (1R,2R)-1,2-cyclohexanediamine is replaced with (1S,2S)-1,2-cyclohexanediamine, which will not be described in detail. S The structural characterization of CP-Im is as follows: Figure 3 and Figure 4 As shown.

[0063] (2) Study on the molecular state properties of exoplatinum circularly polarized luminescent materials

[0064] 1.3mg R CP-Im (2 mmol) was completely dissolved in 2 ml of CHCl3 solvent and heated until dissolved. This concentration is 1*10⁻⁶. -3 mol / L. Then, different concentrations were prepared by sequential dilution. R CP-Im solution. After cooling to room temperature, the FL and CPL spectra were measured in a 2 mm quartz cuvette. The excitation wavelength for FL was 360 nm, and for CPL it was 360 nm. The results are shown in Figure 5.

[0065] 0.65mg R CP-Im (1 mmol) was completely dissolved in 10 ml of three solvents of different polarities (CHCl3, DMF, and Mes), and heated until dissolved. This concentration is 1*10⁻⁶. -4 mol / L. Then, it was successively diluted to prepare the same concentration (5*10). -5 mol / L) R CP-Im solutions of different polarities were used. After cooling to room temperature, the FL and CPL spectra were measured in a 2 mm quartz cuvette. The excitation wavelength for FL was 360 nm, and for CPL it was 360 nm. The results are shown in Figure 6.

[0066] (3) Preparation and property study of excito-association circularly polarized luminescent materials in aggregate state

[0067] 1.3mg R CP-Im (2 mmol) was completely dissolved in 3 ml of DMF solvent, heated until dissolved, then 1 ml of H2O solvent was added, and the mixture was allowed to cool to precipitate the assembly. This concentration was 5*10. -4 mol / L. The FL and CPL spectra were measured in a 1 mm quartz cuvette, with FL excitation wavelength at 360 nm and CPL excitation wavelength at 360 nm. Results are as follows: Figure 7 As shown.

[0068] 2.6mg R CP-Im (4 mmol) was completely dissolved in 1 ml of CHCl3 solvent and heated until dissolved. Then, 3 ml of acetonitrile (CAN) solvent was added, and the mixture was allowed to cool to precipitate the assembly. This concentration was 5 × 10⁻⁶. -4 mol / L. The FL and CPL spectra were measured in a 1 mm quartz cuvette, with FL excitation wavelength at 360 nm and CPL excitation wavelength at 360 nm. Results are as follows: Figure 8 As shown.

[0069] The figures above show that chiral pyrene rings exhibit stable excimer emission and CPEE properties in both solution and various assemblies. In contrast, the excimer / CPEE of the control molecules are highly dependent on the solvent environment, assembly method, and assembly structure.

[0070] Comparative Example 1

[0071] (1) Preparation and molecular state properties of single-unit molecules

[0072] 115.17 mg of chiral diaminocyclohexanol (1 mmol) and 516.54 mg of pyrene-1,6-dicarboxaldehyde (2 mmol) were completely dissolved in 100 mL of chloroform. The mixture was stirred at room temperature for 7 days. After the reaction was complete, the solvent was removed by rotary evaporation. The product was then recrystallized three times with CHCl3 and MeOH to obtain the target product. S MP-Im. The product is a yellow solid with a yield of 71%. S The structural characterization of MP-Im is as follows: Figure 9 and Figure 10 As shown.

[0073]

[0074] 0.9mg S MP-Im (2 mmol) was completely dissolved in 2 ml of CHCl3 solvent and heated until dissolved. This concentration is 1*10⁻⁶. -3mol / L. Then, different concentrations were prepared by sequential dilution. S MP-Im solution. After cooling to room temperature, the FL and CPL spectra were measured in a 2 mm quartz cuvette. The excitation wavelength for FL was 360 nm, and for CPL, it was 360 nm. The results are as follows: Figure 13 As shown.

[0075] 0.9mg S MP-Im (2 mmol) was dissolved in 10 ml of each of three different polar solvents: CHCl3, DMF, and Mes. The solutions were heated until dissolved. This concentration was 1*10⁻⁶. -4 mol / L. Then dilute sequentially to a concentration of 5*10 mol / L. -5 A mol / L solution was cooled to room temperature and the FL spectrum was measured in a 2 mm quartz cuvette with an FL excitation wavelength of 360 nm. The results are as follows: Figure 15 As shown.

[0076] (2) Preparation and property study of single-element molecular aggregates

[0077] 1.8mg S MP-Im (4 mmol) was completely dissolved in 1 ml of DMF solvent, heated until dissolved, and allowed to cool to precipitate the assembly. This concentration was 4 × 10⁻⁶. -3 mol / L. The FL and CPL spectra were measured in a 1 mm quartz cuvette, with FL excitation wavelength at 360 nm and CPL excitation wavelength at 360 nm. Results are as follows: Figure 16 As shown.

[0078] 1.8mg S MP-Im (4 mmol) was completely dissolved in 2 ml of Mes solvent, heated until dissolved, and allowed to cool to precipitate the assembly. This concentration was 2 × 10⁻³ mol / L. The FL and CPL spectra were measured in a 1 mm quartz cuvette, with FL excitation wavelength at 360 nm and CPL excitation wavelength at 360 nm. The results are as follows: Figure 16 As shown.

[0079] The above figures show that in the molecular state and the assembled state, S The excimer / CPEE of MP-Im molecules is significantly affected by concentration and solvent polarity, and within the assembly, under different polarities... S The orientation of the CPL in MP-Im molecules is reversed. The excimer / CPEE of single-element molecules is highly dependent on the solvent environment, assembly method, and assembly structure.

[0080] Comparative Example 2

[0081] (1) Preparation and molecular state properties of bimodal molecules

[0082] 114.19 mg of chiral cyclohexanediamine (1 mmol) and 460 mg of 1-pyrenecarboxaldehyde (2 mmol) were completely dissolved in 100 mL of chloroform. The mixture was stirred at room temperature for 3–5 days. After the reaction was complete, the solvent was removed by rotary evaporation. The product was then recrystallized three times with CHCl3 and MeOH to obtain the final product. R DP-Im. The product is a pale yellow solid with a yield of 67%. R The structural characterization of DP-Im is as follows Figure 11 and Figure 12 As shown.

[0083]

[0084] 1.08mg R DP-Im (2 mmol) was completely dissolved in 2 ml of CHCl3 solvent and heated until dissolved. This concentration is 1*10⁻⁶. -3 mol / L. Then, different concentrations were prepared by sequential dilution. R DP-Im solution. After cooling to room temperature, the FL and CPL spectra were measured in a 2 mm quartz cuvette. The excitation wavelength for FL was 360 nm, and for CPL, it was 360 nm. The results are as follows: Figure 14 As shown.

[0085] 1.08mg R DP-Im (2 mmol) was dissolved in 10 ml of each of three different polar solvents: CHCl3, DMF, and Mes. The solutions were heated until dissolved, resulting in a concentration of 1 × 10⁻⁶. -4 mol / L. Then dilute sequentially to a concentration of 5*10 mol / L. -5 A mol / L solution was cooled to room temperature and the FL spectrum was measured in a 2 mm quartz cuvette with an FL excitation wavelength of 360 nm. The results are as follows: Figure 15 As shown.

[0086] (2) Preparation and property study of bimodal molecular aggregates

[0087] 5.4mg R DP-Im (10 mmol) was completely dissolved in 0.1 ml of DMF solvent, heated until dissolved, and allowed to cool to precipitate the assembly. This concentration was 1*10. -1 mol / L. The FL and CPL spectra were measured in a 1 mm quartz cuvette, with FL excitation wavelength at 360 nm and CPL excitation wavelength at 360 nm. Results are as follows: Figure 17 As shown.

[0088] 5.4mg R DP-Im (10 mmol) was completely dissolved in 0.1 ml of Mes solvent, heated until dissolved, and allowed to cool to precipitate the assembly. This concentration was 1*10.-1 mol / L. The FL and CPL spectra were measured in a 1 mm quartz cuvette, with FL excitation wavelength at 360 nm and CPL excitation wavelength at 360 nm. Results are as follows: Figure 17 As shown.

[0089] The above figures show that in the molecular state and the assembled state, R The luminescent properties of DP-Im molecules that are stable are affected by concentration and solvent.

[0090] Comparing the properties of the molecular and aggregated states of Example 1, Comparative Example 1, and Comparative Example 2, the results showed that, in the molecular state, the chiral pyrene cyclophenone molecule... R CP-Im produced entirely excimer luminescence, with no monomer luminescence whatsoever. Furthermore, the excimer luminescence wavelength was independent of both solution concentration and solvent type. In contrast, under the same conditions, the excimer luminescence of the control molecule was highly dependent on both solution concentration and solvent type. Moreover, comparative studies of the aggregation state properties of Example 1, Comparative Example 1, and Comparative Example 2 revealed that even in the assembled state, the chiral pyrene cyclophenone molecule… R The CP-Im molecule still exhibits stable excimer emission and CPEE performance, while under the same conditions, the excimer / CPEE of the control molecule is still heavily dependent on the solvent environment, assembly method, and assembly structure.

[0091] The present invention has been described in detail above. Those skilled in the art will recognize that the invention can be practiced in a wide range of ways with equivalent parameters, concentrations, and conditions without departing from its spirit and scope. While specific embodiments have been provided, it should be understood that further modifications can be made to the invention. In summary, according to the principles of the invention, this application is intended to include any changes, uses, or improvements to the invention, including modifications made using conventional techniques known in the art that depart from the scope disclosed herein.

Claims

1. A circularly polarized excitopolymer luminescent molecule, the structural formula of which is shown in formula (I) or formula (II): In formulas (I) and (II), R is simultaneously a group as shown in formula 1, or simultaneously a group as shown in formula 5, or simultaneously a group as shown in formula 6:

2. The method for preparing the circularly polarized excimer luminescent molecule according to claim 1 comprises the following steps: in a solvent, chiral 1,2-cyclohexanediamine undergoes a dynamic covalent reaction with a dialdehyde derivative of a polycyclic aromatic hydrocarbon to obtain the circularly polarized excimer luminescent molecule.

3. The method for preparing circularly polarized excitopolymer luminescent molecules according to claim 2, characterized in that: The solvent is at least one selected from N,N-dimethylformamide, water, chloroform, tetrahydrofuran, toluene, and mesitylene. The chiral 1,2-cyclohexanediamine is (1R,2R)-1,2-cyclohexanediamine or (1S,2S)-1,2-cyclohexanediamine; The molar ratio of the chiral 1,2-cyclohexanediamine to the dialdehyde derivative of the polycyclic aromatic hydrocarbon is 1.05:

1. The dynamic covalent reaction of the imine bond is carried out at a temperature of 15–30 °C for 3–7 days.

4. A circularly polarized excimer luminescent material, which is a supramolecular assembly of the circularly polarized excimer luminescent molecules as described in claim 1.

5. The method for preparing the circularly polarized excitopolymer luminescent material according to claim 4, comprising the following steps: The circularly polarized excimer luminescent molecules are added to an organic solvent, heated until dissolved, then a poor solvent is added, cooled, and the precipitated product is collected to obtain the circularly polarized excimer luminescent material.

6. The method for preparing the circularly polarized excimer luminescent material according to claim 5, characterized in that: The organic solvent is at least one selected from N,N-dimethylformamide, water, chloroform, tetrahydrofuran, toluene, and mesitylene. The ratio of the circularly polarized excimer luminescent molecule to the organic solvent is 1 mmol: (0.5–3) mL; The unsuitable solvents are acetonitrile, water, n-hexane, methanol, or ethanol; The volume ratio of the organic solvent to the undesirable solvent is 1:(0.3-3).

7. The application of the circularly polarized excimer luminescent molecule of claim 1 or the circularly polarized excimer luminescent material of claim 4 in circularly polarized luminescence.

8. An application device made of the circularly polarized excimer luminescent material of claim 4.

9. The application device according to claim 8, characterized in that: The application device is at least one of anti-counterfeiting devices, 3D displays, OLEDs, chiral separation membranes, and optoelectronic devices.

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