A luminescent liquid crystal racemate, chiral luminescent molecules and methods for their preparation

Abstract

The present application relates to a kind of luminescent liquid crystal racemate, chiral light-emitting molecule and preparation method thereof.The luminescent liquid crystal racemate is structural formula as shown in formula (rac)-IV: Wherein R 1 , R 2 Independently selected from substituted or non-substituted alkyl.The luminescent liquid crystal racemate of structural formula as shown in formula (rac)-IV provided by the present application has nematic phase liquid crystal properties at room temperature.A small amount of single chiral isomer is added in the luminescent liquid crystal racemate with nematic phase liquid crystal properties at room temperature, slightly increase its ee value, i.e.chiral luminescent liquid crystal with chiral nematic phase liquid crystal properties at room temperature can be obtained.Due to the amount of single chiral isomer is greatly reduced, so the cost of forming chiral liquid crystal is greatly reduced.The blue fluorescence emitted by the chiral luminescent liquid crystal provided by the present application itself and the red fluorescence emitted by the doped system are both circularly polarized luminescence, and the circularly polarized luminescence asymmetry factor of red light after doping can be as high as 0.13.

Description

TECHNICAL FIELD

[0001] The present application relates to the technical field of liquid crystals, in particular to a luminescent liquid crystal racemate, a chiral luminescent molecule and a preparation method thereof. BACKGROUND

[0002] There are mainly two ways to realize circularly polarized luminescence through a liquid crystal system: 1. doping a chiral agent and a non-chiral luminescent dye in a commercial non-chiral nematic liquid crystal (such as 5CB, E7, etc.); 2. directly synthesizing a chiral luminescent liquid crystal.

[0003] Among them, although the chiral doping system has been studied more, it often faces problems such as a large number of additive types, poor molecular matching, and easy phase separation of luminescent dyes, resulting in a complex system and difficult adjustment. In addition, due to the need to consider the introduction of molecular chirality, liquid crystal performance and luminescent performance, the design of molecules is difficult, so there are fewer reports. In addition, the existing chiral luminescent liquid crystals have the following problems: high phase transition temperature, resulting in a non-liquid crystal state at room temperature; composed of a single enantiomer of a compound, high cost; the circularly polarized luminescence asymmetry factor is low, usually 10 -2 orders of magnitude.

[0004] At present, patent CN118064161A discloses a chiral luminescent molecule with cyano diaryl ethylene as a luminescent nucleus and an alkylene cyclohexane as a chiral unit. However, the liquid crystal phase interval temperature of the chiral luminescent molecule is as high as 100 degrees Celsius or more, and it crystallizes at room temperature, with a circularly polarized luminescence asymmetry factor (g lum ) at room temperature of only 2.1x10 -2 ; in addition, a pure chiral sample with a high ee value (ee>99%) is needed to realize the corresponding chiral optical properties, resulting in a large amount of use of a single enantiomer, and the single enantiomer is obtained by chiral column separation, with a high cost (>10000 yuan / gram).

[0005] Therefore, the prior art still needs to be improved and developed. SUMMARY

[0006] In view of the above problems of the prior art, the present application aims to provide a luminescent liquid crystal racemate, a chiral luminescent molecule and a preparation method thereof, which solves the problems of high liquid crystal phase interval temperature, large amount of use of a single enantiomer, and low circularly polarized luminescence asymmetry factor of the existing chiral luminescent molecule with cyano diaryl ethylene as a luminescent nucleus and an alkylene cyclohexane as a chiral unit.

[0007] The technical scheme of the present application is as follows:

[0008] In a first aspect, the present application provides a luminescent liquid crystal racemate, wherein the luminescent liquid crystal racemate is a racemic 1-(2-cyanostyrylphenyl)-4-alkylidene cyclohexane compound, and the structure of the racemic 1-(2-cyanostyrylphenyl)-4-alkylidene cyclohexane compound is shown in formula (rac)-IV:

[0009] wherein R 1 , R 2 are independently selected from substituted or unsubstituted alkyl.

[0010] Optionally, the substituted or unsubstituted alkyl is selected from at least one of alkyl having 1-12 carbon atoms.

[0011] In a second aspect, the present application provides a chiral luminescent molecule, wherein the chiral luminescent molecule is a chiral 1-(2-cyanostyrylphenyl)-4-alkylidene cyclohexane compound, which is a single enantiomer of the luminescent liquid crystal racemate of the first aspect, and the structure of the chiral 1-(2-cyanostyrylphenyl)-4-alkylidene cyclohexane compound is shown in formula (S)-IV or formula (R)-IV:

[0012]

[0013] wherein R 1 , R 2 are independently selected from substituted or unsubstituted alkyl.

[0014] Optionally, the substituted or unsubstituted alkyl is selected from at least one of alkyl having 1-12 carbon atoms.

[0015] In a third aspect, the present application provides a preparation method of the luminescent liquid crystal racemate, comprising the following steps:

[0016] reacting a compound shown in formula 1 with a phosphorus ylide in an organic solvent to obtain a racemate shown in formula (rac)-2;

[0017] reacting the racemate shown in formula (rac)-2 with diisobutylaluminum hydride in an organic solvent to obtain a racemate shown in formula (rac)-3;

[0018] reacting the racemate shown in formula (rac)-3 with a phenylacetonitrile derivative and a base in an organic solvent to obtain a racemic 1-(2-cyanostyrylphenyl)-4-alkylidene cyclohexane compound shown in formula (rac)-IV, i.e. the luminescent liquid crystal racemate;

[0019] wherein R 1 , R2 independently selected from substituted or unsubstituted alkyl;

[0020] The above reaction formula is shown as follows:

[0021]

[0022] In a fourth aspect, the present application provides a preparation method of the chiral luminescent molecule, comprising the steps of:

[0023] reacting the compound shown in formula 1 with phosphorus ylide in an organic solvent to obtain a racemate shown in formula (rac)-2;

[0024] reacting the racemate shown in formula (rac)-2 with diisobutylaluminum hydride in an organic solvent to obtain a racemate shown in formula (rac)-3;

[0025] separating the racemate shown in formula (rac)-3 by chiral column chromatography to obtain a pair of single enantiomers (S)-3 and (R)-3;

[0026] reacting (S)-3 or (R)-3 respectively with phenylacetonitrile derivative and base in an organic solvent to obtain chiral 1-(2-cyanostyrylphenyl)-4-alkylidene cyclohexane compounds shown in formula (S)-IV or (R)-IV, i.e. the chiral luminescent molecule;

[0027] wherein R 1 , R 2 independently selected from substituted or unsubstituted alkyl;

[0028] The above reaction formula is shown as follows:

[0029]

[0030] Optionally, the molar ratio of the compound shown in formula 1 to phosphorus ylide is 2:1-1:2;

[0031] The temperature for the reaction of the compound shown in formula 1 with phosphorus ylide in an organic solvent is -80-40oC, and the reaction time is 1-24 hours.

[0032] Optionally, the organic solvent used for the reaction of the compound shown in formula 1 with phosphorus ylide is at least one of tetrahydrofuran, methyl tetrahydrofuran, diethyl ether, dioxane.

[0033] Optionally, the molar ratio of the racemate shown in formula (rac)-2 to diisobutylaluminum hydride is 1:0.9-1:1.1;

[0034] The organic solvent used for reacting the racemate shown in formula (rac)-2 with diisobutylaluminum hydride is at least one of chloroform, dichloromethane, and dibromoethane;

[0035] The temperature for reacting the racemate shown in formula (rac)-2 with diisobutylaluminum hydride in an organic solvent is -80-30 DEG C, and the reaction time is 1-6 hours.

[0036] Optionally, the solvent system used for separating the racemate shown in formula (rac)-3 by chiral column chromatography is n-hexane and ethanol, and the volume ratio of the two is 95:5 to 99.5:0.5.

[0037] The chiral column used for separating the racemate shown in formula (rac)-3 by chiral column chromatography is at least one of AY and OY.

[0038] Optionally, the base used for reacting with (S)-3 or (R)-3 is at least one of sodium methoxide, sodium ethoxide, sodium hydroxide, and piperidine.

[0039] Optionally, the organic solvent used for the reaction is at least one of methanol, ethanol, and pyridine.

[0040] Optionally, the temperature for reacting (S)-3 or (R)-3 with the phenylacetonitrile derivative and the base in the organic solvent is 40-120 DEG C, and the reaction time is 6-48 hours.

[0041] Compared with the prior art, the present application has the following beneficial effects:

[0042] Based on the aforementioned molecular design, the present application removes one benzene ring in the cyanodiarylethylene light-emitting mother nucleus to obtain a light-emitting liquid crystal racemate shown in formula (rac)-IV, which has a nematic phase at room temperature.

[0043] The present application adds a small amount of single chiral isomer (R)-IV or (S)-IV to the light-emitting liquid crystal racemate shown in formula (rac)-IV, which has a nematic phase at room temperature, to slightly increase the ee value (the minimum can be 1% ee), so as to obtain a chiral light-emitting liquid crystal having a cholesteric phase (chiral nematic phase) at room temperature. Since the amount of the single chiral isomer is greatly reduced (the minimum is only 1%), the cost of forming the chiral liquid crystal is reduced by nearly 100 times compared with the aforementioned system.

[0044] The chiral luminescent liquid crystal emits blue fluorescence under ultraviolet excitation, and after doping with a red dye, the system can emit red fluorescence under ultraviolet excitation through fluorescence resonance energy transfer. Both the blue fluorescence emitted by the chiral luminescent liquid crystal and the red fluorescence emitted by the doped system are circularly polarized light, and the circularly polarized light asymmetry factor of the red light after doping can be as high as 0.13. BRIEF DESCRIPTION OF DRAWINGS

[0045] Figure 1 A differential scanning calorimetry (DSC) graph of a luminescent liquid crystal racemate having a structural formula as shown in formula (rac)-IV.

[0046] Figure 2 A polarizing microscope (POM) graph of a luminescent liquid crystal racemate having a structural formula as shown in formula (rac)-IV at 25°C.

[0047] Figure 3 A POM graph of a chiral luminescent liquid crystal with 1% ee at 25°C.

[0048] Figure 4 A POM graph of a chiral luminescent liquid crystal with 20% ee at 25°C.

[0049] Figure 5 An emission graph of a chiral luminescent liquid crystal under ultraviolet excitation.

[0050] Figure 6 An emission graph of a chiral luminescent liquid crystal after doping with Nile red under ultraviolet excitation, wherein the dashed line indicates the emission graph when the doping amount of Nile red is 0.1 mol%, and the solid line indicates the emission graph when the doping amount of Nile red is 2.0 mol%.

[0051] Figure 7 A circularly polarized light (CPL) graph of a chiral luminescent liquid crystal.

[0052] Figure 8 A CPL graph of a chiral luminescent liquid crystal after doping with Nile red, wherein the black dashed line indicates the CPL graph when the ee of the (S)-IV-based system is 20%, the black solid line indicates the CPL graph when the ee of the (R)-IV-based system is 20%, the green dashed line indicates the CPL graph when the ee of the (S)-IV-based system is 1%, and the green solid line indicates the CPL graph when the ee of the (R)-IV-based system is 1%.

[0053] Figure 9 A g lum graph of a chiral luminescent liquid crystal after doping with Nile red, wherein the black dashed line indicates the g lum graph when the ee of the (S)-IV-based system is 20%, and the black solid line indicates the g lumFigure, the green dashed line refers to g of the system with (S)-IV as the main component and ee of 1% lum Figure, the green solid line refers to g of the system with (R)-IV as the main component and ee of 1% lum Figure. DETAILED DESCRIPTION

[0054] The present application provides a luminescent liquid crystal racemate, a chiral luminescent molecule and a preparation method thereof. In order to make the purpose, technical scheme and effect of the present application more clear and explicit, the present application will be further described in detail below. It should be understood that the specific embodiments described herein are only used to explain the present application and not to limit the present application.

[0055] The present application provides a luminescent liquid crystal racemate, a chiral luminescent molecule and a preparation method thereof. In order to make the purpose, technical scheme and effect of the present application more clear and explicit, the present application will be further described in detail below. It should be understood that the specific embodiments described herein are only used to explain the present application and not to limit the present application.

[0056] wherein R 1 , R 2 are independently selected from substituted or unsubstituted alkyl.

[0057] In one embodiment, the substituted or unsubstituted alkyl is selected from at least one of alkyl groups having a carbon atom number of 1-12.

[0058] The present application provides a chiral luminescent molecule, wherein the chiral luminescent molecule is a chiral 1-(2-cyanostyrylphenyl)-4-alkylidene cyclohexane compound, which is a single enantiomer of the luminescent liquid crystal racemate described in the embodiments of the present application. The structure of the chiral 1-(2-cyanostyrylphenyl)-4-alkylidene cyclohexane compound is shown in formula (S)-IV or formula (R)-IV:

[0059]

[0060] wherein R 1 , R 2 are independently selected from substituted or unsubstituted alkyl.

[0061] A small amount of chiral luminescent molecules is added to the luminescent liquid crystal racemate to obtain a chiral luminescent liquid crystal.

[0062] Compared with the chiral luminescent liquid crystal disclosed in the prior patent CN118064161A, the main improvements of the embodiments of the present application include:

[0063] In order to solve the problem that the phase interval temperature of the existing chiral luminescent liquid crystal is higher than room temperature, the luminescent liquid crystal racemate with the structural formula as shown in formula (rac)-IV is obtained by removing one benzene ring in the cyanodiarylethylene luminescent core based on the aforementioned molecular design.

[0064] In order to solve the problem that the amount of a single enantiomer is large, a small amount of a single chiral isomer (R)-IV or (S)-IV is added to the luminescent liquid crystal racemate with the structural formula as shown in formula (rac)-IV, the ee value of which is slightly increased (the minimum can be 1% ee), so that the chiral luminescent liquid crystal with the cholesteric phase (chiral nematic phase) at room temperature is obtained. Since the amount of the single chiral isomer is greatly reduced (the minimum is only 1%), the cost of forming the chiral liquid crystal is reduced by nearly 100 times compared with the aforementioned system.

[0065] In order to solve the problem that the circularly polarized luminescence asymmetry factor of the existing chiral luminescent liquid crystal is low, the chiral luminescent liquid crystal provided by the embodiment of the present application itself emits blue fluorescence under ultraviolet excitation. By doping a red dye, the system can be converted to emit red fluorescence under ultraviolet excitation through fluorescence resonance energy transfer. The blue fluorescence emitted by the chiral luminescent liquid crystal and the red fluorescence emitted by the doped system are both circularly polarized luminescence, and the circularly polarized luminescence asymmetry factor of the red light after doping can be as high as 0.13.

[0066] In an embodiment, the substituted or unsubstituted alkyl group is selected from at least one of alkyl groups having 1-12 carbon atoms.

[0067] As an example, the chiral luminescent molecule is selected from one of the following structures or an enantiomer thereof:

[0068]

[0069] The embodiment of the present application provides a preparation method of the luminescent liquid crystal racemate as described above, and the preparation method comprises the following steps:

[0070] The compound shown in formula 1 is reacted with a phosphorus ylide in an organic solvent to obtain the racemate shown in formula (rac)-2.

[0071] The racemate shown in formula (rac)-2 is reacted with diisobutylaluminum hydride in an organic solvent to obtain the racemate shown in formula (rac)-3.

[0072] The racemate shown in formula (rac)-3 is reacted with a phenylacetonitrile derivative and a base in an organic solvent to obtain the racemate 1-(2-cyanostyrylphenyl)-4-alkylidene cyclohexane compound with the structural formula as shown in formula (rac)-IV, that is, the luminescent liquid crystal racemate.

[0073] wherein R 1 , R 2 are independently selected from substituted or unsubstituted alkyl;

[0074] The above reaction formula is shown as follows:

[0075]

[0076] In an embodiment, the base used for reacting with the racemate shown in formula (rac)-3 is at least one of sodium methoxide, sodium ethoxide, sodium hydroxide, and piperidine.

[0077] In an embodiment, the organic solvent used for reacting with the racemate shown in formula (rac)-3 is at least one of methanol, ethanol, and pyridine.

[0078] In an embodiment, the temperature for reacting the racemate shown in formula (rac)-3 with the phenylacetonitrile derivative and the base in the organic solvent is 40-120℃ (such as 40℃, 60℃, 80℃, 100℃, 120℃, etc.), and the reaction time is 6-48 hours (such as 6 hours, 12 hours, 24 hours, 30 hours, 40 hours, 48 hours, etc.).

[0079] Details of other steps are described below and are not expanded here.

[0080] The embodiment of the present application provides a preparation method of a chiral light-emitting molecule, comprising the following steps:

[0081] reacting the compound shown in formula 1 with a phosphorus ylide in an organic solvent to obtain a racemate shown in formula (rac)-2;

[0082] reacting the racemate shown in formula (rac)-2 with diisobutylaluminum hydride in an organic solvent to obtain a racemate shown in formula (rac)-3;

[0083] separating the racemate shown in formula (rac)-3 by chiral column chromatography to obtain a pair of single chiral enantiomers (S)-3 and (R)-3;

[0084] reacting (S)-3 or (R)-3 respectively with a phenylacetonitrile derivative and a base in an organic solvent to obtain a chiral 1-(2-cyanostyrylphenyl)-4-alkylidene cyclohexane compound shown in formula (S)-IV or formula (R)-IV, i.e. the chiral light-emitting molecule;

[0085] wherein R 1 , R 2 are independently selected from substituted or unsubstituted alkyl;

[0086] The above reaction formula is shown as follows:

[0087]

[0088] A small amount of chiral light-emitting molecules is doped into a light-emitting liquid crystal racemate, i.e. a chiral light-emitting liquid crystal is obtained.

[0089] In an embodiment, the molar ratio of the compound of formula 1 to phosphorus ylide is 2:1-1:2.

[0090] In an embodiment, the organic solvent used for the reaction of the compound of formula 1 with phosphorus ylide is at least one of tetrahydrofuran, methyl tetrahydrofuran, diethyl ether, dioxane.

[0091] In an embodiment, the temperature for the reaction of the compound of formula 1 with phosphorus ylide in an organic solvent is -80-40℃ (such as -80℃, -60℃, -40℃, -20℃, 0℃, 10℃, 20℃, 40℃, etc.), and the reaction time is 1-24 hours (such as 1 hour, 2 hours, 4 hours, 10 hours, 15 hours, 20 hours, 22 hours, 24 hours, etc.).

[0092] In an embodiment, the molar ratio of the racemate of formula (rac)-2 to diisobutylaluminum hydride is 1:0.9-1:1.1, such as 1:1.1.

[0093] In an embodiment, the organic solvent used for the reaction of the racemate of formula (rac)-2 with diisobutylaluminum hydride is at least one of chloroform, dichloromethane, dibromoethane.

[0094] In an embodiment, the temperature for the reaction of the racemate of formula (rac)-2 with diisobutylaluminum hydride in an organic solvent is -80-30℃ (such as -80℃, -60℃, -40℃, -20℃, 0℃, 10℃, 20℃, 30℃, etc.), and the reaction time is 1-6 hours (such as 1 hour, 2 hours, 4 hours, 5 hours, 6 hours, etc.).

[0095] In an embodiment, the solvent system used for the separation of the racemate of formula (rac)-3 by chiral column chromatography is n-hexane and ethanol, and the volume ratio of the two is 95:5 to 99.5:0.5.

[0096] In an embodiment, the chiral column used for the separation of the racemate of formula (rac)-3 by chiral column chromatography is at least one of AY and OY.

[0097] In an embodiment, the base used for the reaction with (S)-3 or (R)-3 is at least one of sodium methoxide, sodium ethoxide, sodium hydroxide, piperidine.

[0098] In one embodiment, the organic solvent used in the reaction of (S)-3 or (R)-3 is at least one of methanol, ethanol, and pyridine.

[0099] In one embodiment, the temperature for the reaction of (S)-3 or (R)-3 with the phenylacetonitrile derivative and the base in the organic solvent is 40-120°C (such as 40°C, 60°C, 80°C, 100°C, 120°C, etc.), and the reaction time is 6-48 hours (such as 6 hours, 12 hours, 24 hours, 30 hours, 40 hours, 48 hours, etc.).

[0100] The application is further described in detail below through specific examples.

[0101] Example 1

[0102] The compound shown in formula 1 is mixed with phosphorus ylide at a molar ratio of 1.13:1 in tetrahydrofuran at -78°C for 12 hours to obtain the racemate shown in formula (rac)-2;

[0103] The racemate shown in formula (rac)-2 is mixed with diisobutylaluminum hydride at a molar ratio of 1:1.1 in dichloromethane at -40°C for 2 hours to obtain the racemate shown in formula (rac)-3;

[0104] The racemate shown in formula (rac)-3 is separated by chiral column chromatography through an AY chiral column, wherein the solvent system used is n-hexane and ethanol at a volume ratio of 98:2, to obtain a pair of single enantiomers (S)-3 and (R)-3;

[0105] (S)-3 or (R)-3 is respectively reacted with a phenylacetonitrile derivative and sodium hydroxide in ethanol at 80°C for 24 hours to obtain a chiral luminescent molecule shown in formula (S)-IV or formula (R)-IV, respectively;

[0106] The racemate shown in formula (rac)-3 is reacted with a phenylacetonitrile derivative and sodium hydroxide in ethanol at 80°C for 24 hours to obtain a luminescent liquid crystal racemate shown in formula (rac)-IV;

[0107] The above reaction formula is shown below:

[0108]

[0109] The luminescent liquid crystal racemate shown in formula (rac)-IV is a nematic liquid crystal at room temperature, and has a liquid crystal phase interval below 26°C, as shown in the attached Figure 1 (racemate DSC) and the attached Figure 2 (racemate POM).

[0110] A small amount of a single chiral isomer is added to the racemic form of the luminescent liquid crystal shown in formula (rac)-IV The chiral luminescent liquid crystal is a cholesteric phase liquid crystal at room temperature with an ee value of 1% to 20%, see attached Figure 3 (1% ee POM) and attached Figure 4 (20% ee POM).

[0111] The chiral luminescent liquid crystal has blue fluorescent emission under UV excitation, see attached Figure 5 .

[0112] The chiral luminescent liquid crystal has red fluorescent emission under UV excitation after doping with 0.1 mol% or 2.0 mol% Nile Red, see attached Figure 6 .

[0113] The chiral luminescent liquid crystal has blue circularly polarized luminescence under UV excitation with an ee value of 1% or 20%, see attached Figure 7 .

[0114] The chiral luminescent liquid crystal has red CPL under UV excitation after doping with 0.1 mol% or 2.0 mol% Nile Red with an ee value of 1% to 20%, see attached Figure 8 (CPL) and attached Figure 9 (g lum ).

[0115] It is to be understood that the application is not limited to the examples described above, which can be modified or adapted by a person of ordinary skill in the art in the light of the above description, all such modifications and adaptations being intended to fall within the scope of the application as defined in the appended claims.

Claims

1. A light-emitting liquid crystal racemic body, characterized in that, The racemic form of the luminescent liquid crystal is a racemic 1-(2-cyanostylenylphenyl)-4-alkylcyclohexane compound, and the structural formula of the racemic 1-(2-cyanostylenylphenyl)-4-alkylcyclohexane compound is shown in formula (). rac As shown in )-IV: , Where R 1 R 2 Independently selected from non-substituted alkyl groups; The unsubstituted alkyl group is selected from at least one of alkyl groups having 1 to 12 carbon atoms.

2. A chiral luminescent molecule, characterized in that, The chiral luminescent molecule is a chiral 1-(2-cyanostynylphenyl)-4-alkylcyclohexane compound, and the structural formula of the chiral 1-(2-cyanostynylphenyl)-4-alkylcyclohexane compound is shown in formula (). S As shown in )-IV or formula ( R As shown in )-IV: or , Where R 1 R 2 Independently selected from non-substituted alkyl groups; The unsubstituted alkyl group is selected from at least one of alkyl groups having 1 to 12 carbon atoms.

3. A method for preparing the racemic form of the luminescent liquid crystal according to claim 1, characterized in that, Including the following steps: The compound shown in Formula 1 was reacted with phosphorus ylide in an organic solvent to obtain the compound of Formula ( rac The racemic mixture shown in )-2; The formula ( rac The racemic mixture shown in )-2 reacts with diisobutylaluminum hydride in an organic solvent to obtain the product of formula ( rac The racemic mixture shown in Figure 3; The formula ( rac The racemic mixture shown in formula 3 reacts with a phenylacetonitrile derivative and a base in an organic solvent to obtain a structure with the following formula ( rac The racemic 1-(2-cyanostylenylphenyl)-4-alkylcyclohexane compound shown in )-IV is the racemic luminescent liquid crystal; Where R 1 R 2 Independently selected from non-substituted alkyl groups; The unsubstituted alkyl group is selected from at least one of alkyl groups having 1 to 12 carbon atoms; The above reaction formula is shown below: 。 4. A method for preparing the chiral luminescent molecule according to claim 2, characterized in that, Including the following steps: The compound shown in Formula 1 was reacted with phosphorus ylide in an organic solvent to obtain the compound of Formula ( rac The racemic mixture shown in )-2; The formula ( rac The racemic mixture shown in )-2 reacts with diisobutylaluminum hydride in an organic solvent to obtain the product of formula ( rac The racemic mixture shown in Figure 3; The formula ( rac The racemic mixture shown in )-3 was separated by chiral column chromatography to yield a pair of enantiomers with single chirality. S )-3 and ( R -3; Will( S )-3 or ( R )-3 reacts with phenylacetonitrile derivatives and bases in organic solvents to obtain structures as shown in formula ( S As shown in )-IV or formula ( R The chiral 1-(2-cyanostylenylphenyl)-4-alkylcyclohexane compound shown in )-IV is the chiral luminescent molecule; Where R 1 R 2 Independently selected from non-substituted alkyl groups; The unsubstituted alkyl group is selected from at least one of alkyl groups having 1 to 12 carbon atoms; The above reaction formula is shown below: 。 5. The method according to claim 4, characterized in that, The molar ratio of the compound shown in Formula 1 to phosphorus ylide is 2:1 to 1:2; The reaction temperature of the compound represented by Formula 1 with phosphorus ylide in an organic solvent is -80 to 40°C. o C, the reaction time is 1-24 hours.

6. The method according to claim 4, characterized in that, The organic solvent used for the reaction of the compound represented by Formula 1 with phosphorus ylide is at least one of tetrahydrofuran, methyltetrahydrofuran, diethyl ether, and dioxane.

7. The method according to claim 4, characterized in that, The formula ( rac The molar ratio of the racemic mixture shown in )-2 to diisobutylaluminum hydride is 1:0.9-1:1.1; The formula ( rac The organic solvent used for the reaction of the racemic mixture shown in )-2 with diisobutylaluminum hydride is at least one of chloroform, dichloromethane, and dibromoethane; The formula ( rac The reaction temperature of the racemic mixture shown in )-2 with diisobutylaluminum hydride in an organic solvent is -80 to -30°C. o C, the reaction time is 1-6 hours.

8. The method according to claim 4, characterized in that, The formula ( rac The solvent system used for the separation of the racemic mixture shown in )-3 by chiral column chromatography was n-hexane and ethanol, with a volume ratio of 95:5 to 99.5:0.

5. The formula ( rac The racemic mixture shown in )-3 was separated by chiral column chromatography using at least one of AY and OY columns; The and ( S )-3 or ( R The base for the reaction )-3 is at least one of sodium methoxide, sodium ethoxide, sodium hydroxide, and piperidine; The and ( S )-3 or ( R The organic solvent used in the reaction is at least one of methanol, ethanol, and pyridine. The ( S )-3 or ( R The reaction temperature of 3- with phenylacetonitrile derivatives and bases in organic solvents is 40-120°C. o C, the reaction time is 6-48 hours.

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