Novel liquid crystal supramolecular compound and preparation method thereof

Abstract

The invention discloses a novel liquid crystal supramolecular compound and a preparation method thereof. The liquid crystal property and the light response property of the compound are mainly tested by methods such as POM (Polyoxymethylene), UV (Ultraviolet) and the like. The compound can form a smectic phase (SmA), the photoresponse property of the compound is researched through an ultraviolet spectrum, and the result shows that the compound has the stratified phase (SmA), has good photoresponse behavior and reversible photophysical properties, and is expected to be used for photoelectric molecular switches.

Description

Technical Field

[0001] The present invention relates to the technical field of new materials, and in particular to a novel liquid crystal supramolecular compound and a preparation method thereof. Background Art

[0002] Liquid crystal is a soft substance between solid and liquid, possessing the anisotropy of solids while also possessing the continuity and fluidity of liquids. Since its discovery, liquid crystals have been widely used in various fields, such as household appliances, industrial equipment, and GPS navigation systems. It can be said that liquid crystals are ubiquitous.

[0003] As a liquid crystal photosensitive material, azobenzene liquid crystal molecules based on pillar[5]arene are very attractive. Conventional polymer photosensitive materials have uncertain compositions, and simple azobenzene derivatives undergo severe hydrogen polymerization, while pillar[5]arene azobenzene liquid crystal molecules overcome these shortcomings. The tubular pillar[5]arene macrocyclic skeleton provides sufficient free space for azobenzene to achieve reversible photoisomerization, so they exhibit excellent light-triggered modulation of surface free energy, wettability, and photoinduced orientation.

[0004] Liquid crystals can be classified based on a variety of criteria. Due to the different shapes of the molecules, they can be divided into three categories: banana-shaped, rod-shaped, and disc-shaped liquid crystals. Due to differences in molecular weight, they can be divided into two major categories: liquid crystal polymers and small molecule liquid crystals. Due to their different compositional conditions and components, liquid crystals can be divided into lyotropic and thermotropic liquid crystals. Thermotropic liquid crystals are pure substances whose liquid crystal properties change with temperature. Lyotropic liquid crystals, on the other hand, are mixtures whose properties change in different solvents and concentrations.

[0005] Thermotropic liquid crystals can be divided into three main categories: nematic, cholesteric, and smectic phases, with Smectic A and Smectic C being the most common. In the smectic phase, liquid crystal molecules are arranged in layers, with their principal axes parallel within the layers. In the SmA phase, the orientation of the liquid crystal compounds is perpendicular to the layers, while in the SmC phase, the liquid crystal axes are tilted relative to the layers. Molecules can move back and forth and left and right, but not between upper and lower layers. Because the smectic phase is ordered, it typically occurs at low temperatures. In the nematic phase, the principal axes of the molecules remain essentially parallel, but the center of mass is more disorganized than in the smectic phase, resulting in greater mobility. Most cholesteric liquid crystal molecules are derivatives of cholesterol, have a helical structure, and are highly optically active. These molecules are, in fact, a special form of the nematic phase. Other phases include the blue phase, columnar phase, and three-dimensional cubic phase.

[0006] Obtaining liquid crystal materials through a series of methods is particularly important in today's society. Designing and synthesizing a series of liquid crystal molecules and studying their properties is one of the current hot topics in the field of liquid crystal research. Summary of the Invention

[0007] In view of the above technical problems, the first object of the present invention is to provide a liquid crystal molecular compound, and the second object is to provide a method for preparing the compound. The compound has a smectic phase (SmA) and has good photoresponse behavior.

[0008] In order to achieve the above first objective, the present invention provides a novel liquid crystal supramolecular compound having the structural formula:

[0009]

[0010] The second object of the present invention is achieved as follows: the preparation method of the novel liquid crystal supramolecular compound is characterized in that: using p-nitrophenol as a starting material, reacting under alkaline conditions to obtain intermediate 1; methyl gallate reacts with dodecyl bromide to obtain intermediate 2, intermediate 2 is reduced to obtain intermediate 3, intermediate 3 is chlorinated to obtain intermediate 4, intermediate 1 and intermediate 4 react to obtain intermediate 5, intermediate 5 reacts with propargyl bromide to obtain intermediate 6; 1,4-dioxyethyl bromide reacts with (CH2O) n The reaction generates intermediate 7, which reacts with sodium azide to generate intermediate 8, which reacts with intermediate 6 to generate the target product;

[0011] The reaction formula is:

[0012]

[0013] In the above scheme, the synthesis of intermediate 1 is as follows: KOH and water are added to a reaction vessel, stirred under ice bath conditions until cooled to room temperature, p-nitrophenol is added, the reaction is started at 120°C, and after the temperature reaches 120°C, the temperature is heated to 200°C at a rate of 5°C per time until the reaction is complete. After the reaction is completed, the reaction is cooled to room temperature, water is added to the reaction vessel, the pH value of the solution is adjusted to 3-4 with dilute HCl, and extraction is performed with ethyl acetate. The organic layer is dried and evaporated to dryness under reduced pressure to obtain a yellow crude product. The crude product is separated and purified by column chromatography to obtain intermediate 1.

[0014] In the above scheme, the synthesis of intermediate 2 is as follows: methyl gallate and K2CO3 are added to a reaction vessel, N,N-dimethylformamide is added as a solvent, and the reaction is refluxed; dodecyl bromide is slowly added to the reaction solution, and the reaction is continued until the reaction is complete. The reaction solution is cooled to room temperature, and water and ethyl acetate are added to extract the upper organic layer. The organic layer is washed with a saturated NaCl solution, dried over anhydrous sodium sulfate, the solvent is evaporated, and purified by column chromatography to obtain intermediate 2.

[0015] In the above scheme, the synthesis of intermediate 3 is as follows: THF and intermediate 2 are added to a flask, LiAlH4 is added under ice bath conditions, and the reaction is carried out at room temperature until the reaction is complete. Water is slowly added dropwise to the reaction solution under ice bath conditions, and a large amount of bubbles and white solids are observed. Then, dilute HCl is added until no bubbles are generated. The organic layer is extracted with dichloromethane, dried over anhydrous sodium sulfate, and the solvent is evaporated to obtain intermediate 3.

[0016] In the above scheme, the synthesis of intermediate 4 is as follows: THF, DMF and intermediate 3 are added to a reaction vessel, stirred, thionyl chloride is added dropwise and reacted at room temperature until the reaction is complete, and the solvent is distilled off under reduced pressure to obtain intermediate 4.

[0017] In the above scheme, the synthesis of intermediate 5 is as follows: intermediate 4, intermediate 1, and K2CO3 are added to a reaction vessel, and then DMF is added until completely dissolved. The reaction is refluxed until the reaction is completed, cooled to room temperature, water is added, and filtered. The obtained product is dissolved in ethyl acetate, dried over anhydrous sodium sulfate, and evaporated to dryness under reduced pressure. The intermediate 5 is purified by column chromatography to obtain intermediate 5.

[0018] In the above scheme, the synthesis of intermediate 6 is as follows: potassium carbonate, intermediate 5, solvent CH3CN and propargyl bromide are added to a reaction vessel, the reaction is refluxed until the reaction is complete, the reaction solution is cooled to room temperature, the solvent is evaporated under reduced pressure, and then the organic layer is extracted with water and dichloromethane, washed with aqueous NaOH solution and saturated brine and then dried, the solvent is evaporated under reduced pressure, and the crude product is separated and purified by column chromatography to obtain intermediate 6.

[0019] In the above scheme: the synthesis of intermediate 7 is to convert (CH2O) n , 1,4-dioxoethyl bromide was added to the reaction vessel; chloroform was added to dissolve, boron trifluoride ether was added dropwise, and the reaction was carried out at room temperature until the reaction was completed, water was added, and CH2Cl2 was extracted. The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The intermediate 7 was separated and purified by column chromatography.

[0020] In the above scheme: the synthesis of intermediate 8 is as follows: intermediate 7, NaN3, KI and DMF are added to a reaction vessel, dissolved, refluxed until the reaction is complete, cooled to room temperature, added with water, extracted with CH2Cl2, the organic layer is washed with saturated sodium chloride, dried over anhydrous sodium sulfate, and the solvent is evaporated to obtain intermediate 8.

[0021] In the above scheme, the synthesis of intermediate 9 is as follows: cuprous iodide, intermediate 6, and intermediate 8 are added to a reaction vessel, anhydrous THF and anhydrous DMF are added to dissolve the solid compounds, N2 protection is applied, the reaction is completed at 75°C, and the mixture is cooled to room temperature; water is added, followed by extraction with CHCl3, the organic layer is washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent is evaporated, and the product is separated and purified by column chromatography to obtain the product.

[0022] Beneficial effects: This paper designed and synthesized azide compounds using p-nitrophenol and methyl gallate as raw materials, and synthesized the required pillar[5]arene terminal alkynes from p-diphenol. Finally, a new azobenzotriazole liquid crystal compound based on pillar[5]arene was designed and synthesized using the Click reaction as the core. The liquid crystal properties and photoresponse properties of the compound were mainly tested by POM and UV methods. The compound can form a smectic phase (SmA). Its photoresponse properties were studied by UV spectroscopy. The results showed that the compound has a smectic phase (SmA), has good photoresponse behavior and reversible photophysical properties, and is expected to be used in photoelectric molecular switches. BRIEF DESCRIPTION OF THE DRAWINGS

[0023] Figure 1 is the hydrogen nuclear magnetic resonance spectrum of the target product of the present invention.

[0024] Figure 2 The carbon-1NMR spectrum of the target product of the present invention is shown in FIG.

[0025] Figure 3 These are the POM texture images of the target product, where a: texture observed at 60°C, b: texture observed at 90°C, c: texture observed at 118°C, and d: texture observed at 121°C.

[0026] Figure 4 Schematic diagram of the formation of a smectic phase (SmA) by the target product of the triazole class of the present invention.

[0027] Figure 5 The target compound 9 was prepared in dichloromethane (c=10 -5 UV absorption spectra in M): (a) irradiated with 365 nm UV light, (b) under visible light irradiation. DETAILED DESCRIPTION

[0028] The present invention will be further described below by way of examples:

[0029] Example 1

[0030] Synthesis of intermediate 1

[0031]

[0032] To a round-bottom flask, add KOH (30 g, 534 mmol) and water (6 mL). Stir in an ice bath until cooled to room temperature. Then, add p-nitrophenol (4.7 g, 33.8 mmol). The reaction begins at 120°C (after reaching 120°C, heat to 200°C in 5°C increments) and proceeds for 4 h. Thin-layer chromatography confirms the reaction is complete. After the reaction is complete, allow the product to cool to room temperature, add an appropriate amount of water to the round-bottom flask, and then pour it into a beaker. Adjust the pH of the solution to approximately 3-4 with dilute HCl (2 M), then extract with ethyl acetate (30 mL x 3). The organic layers are combined, dried, and evaporated to dryness under reduced pressure to yield a crude yellow product. The crude product is purified by column chromatography (petroleum ether:ethyl acetate = 2:1). 1.4 g of an orange-yellow solid is obtained, with a yield of 25%.

[0033] Example 2

[0034] Synthesis of intermediate 2:

[0035]

[0036] Methyl gallate (1 g, 5.4 mmol) and K2CO3 (4.5 g, 32.6 mmol) were added to a round-bottom flask, and N,N-dimethylformamide (30 mL) was used as solvent. The mixture was refluxed at 95°C for 0.5 h. C 12 H 25 Br(dodecyl bromide) (5.8 mL, 21.7 mmol) was added and the reaction was continued for 12 h. After the reaction was completed, the solution was observed to be black, and the reaction solution was then cooled to room temperature. Water (10 mL) and ethyl acetate (30 mL) were added to a separatory funnel and extracted to obtain the upper organic layer. The organic layer was then washed with saturated NaCl (30 mL × 5 times) and dried over anhydrous sodium sulfate. The solvent was evaporated to dryness, and the crude product was purified by column chromatography (petroleum ether:ethyl acetate = 60:1). 4.0 g of a white solid was obtained, with a calculated yield of 92%.

[0037] Example 3

[0038] Synthesis of intermediate 3:

[0039]

[0040] THF (15 mL) and intermediate 2 (2.4 g, 4.8 mmol) were added to a flask. LiAlH4 (0.18 g, 6.0 mmol) was added under ice-bath conditions and the reaction was continued at room temperature for 12 h. After the reaction was completed, water was slowly added dropwise to the reaction solution under ice-bath conditions. A large amount of bubbles and white solid were observed. Dilute HCl (2 M) was then added until no bubbles were generated. The organic layer was extracted with CH2Cl2 (30 mL × 3 times), dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. 2.8 g of white solid product was obtained, with a calculated yield of 93%.

[0041] Example 4

[0042] Synthesis of intermediate 4:

[0043]

[0044] THF (20 mL), DMF (2-3 drops), and intermediate 3 (2.8 g, 3.8 mmol) were added to a round-bottom flask and stirred. Thionyl chloride (0.3 mL, 4.8 mmol) was then added dropwise and allowed to react at room temperature for 12 h. After the reaction was complete, the solvent was removed by vacuum distillation at approximately 60°C. 2.5 g of a white solid was obtained with a yield of 90%.

[0045] Example 5

[0046] Synthesis of intermediate 5:

[0047]

[0048] Intermediate 4 (3.2 g, 4.2 mmol), intermediate 1 (3.2 g, 4.2 mmol), and K2CO3 (1.7 g, 2.6 mmol) were added to a round-bottom flask and completely dissolved in DMF (20 mL). The mixture was refluxed at 90°C for 10 h. After the reaction was completed, the reaction solution was cooled to room temperature, and water was added directly to the flask. The resulting product was dissolved in ethyl acetate, dried over anhydrous sodium sulfate, and evaporated to dryness under reduced pressure. The crude product was then isolated and purified by column chromatography (ethyl acetate:petroleum ether = 1:5). 0.74 g of the yellow solid product was obtained, with a calculated yield of 20%.

[0049] Example 6

[0050] Synthesis of intermediate 6:

[0051]

[0052] K2CO3 (0.18 g, 1.3 mmol) and intermediate 5 (0.13 g, 0.15 mmol) were added to a round-bottom flask, followed by CH3CN (15 mL) and propargyl bromide (0.02 mL, 0.23 mmol). The reaction was refluxed at 80°C for 12 h. After the reaction was complete, the reaction solution was cooled to room temperature and the solvent was evaporated under reduced pressure. The organic layer was then extracted with water and CH2Cl2 (20 mL x 3). The organic layer was then washed with a 2.5 M aqueous NaOH solution and saturated brine before drying. The CH2Cl2 was evaporated under reduced pressure, and the crude product was separated and purified by column chromatography (petroleum ether:ethyl acetate = 10:1). 0.11 mg of the yellow product was obtained in an 18% yield.

[0053] Example 7

[0054] Synthesis of intermediate 7:

[0055]

[0056] (CH2O) n (750 mg) and 1,4-dioxoethyl bromide (4 g, 13.5 mmol) were added to a round-bottom flask; CHCl₃ (75 mL) was added as a solvent for dissolution, and boron trifluoride etherate (3 mL, 2.67 mmol) was added dropwise. The mixture was allowed to react at room temperature for 3 h. After the reaction, water was added to the round-bottom flask, and then extracted with CH₂Cl₂ (20 mL x 3) in a separatory funnel. The resulting organic layer was dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure. Finally, the crude white product was isolated and purified by column chromatography (petroleum ether:dichloromethane = 1:1). 0.65 g of a white solid was obtained, with a yield of 15.56%.

[0057] Example 8

[0058] Synthesis of intermediate 8:

[0059]

[0060] Intermediate 7 (0.11 g, 0.057 mmol), NaN (0.056 g, 0.861 mmol), and KI (0.1 g, 0.6 mmol) were added to a round-bottom flask and dissolved in DMF. The mixture was then refluxed at 95°C for 12 h. After cooling to room temperature to confirm completion of the reaction, a suitable amount of water (15 mL) was added. The mixture was extracted with CHCl (30 mL x 3). The lower organic layer was then washed with saturated NaCl (20 mL x 2) and dried over anhydrous NaSO. The solvent was evaporated to afford Intermediate 8 as a white solid (0.085 g, 96% yield).

[0061] Example 9

[0062] Synthesis of target product 9:

[0063]

[0064] Cuprous iodide (0.019 g, 0.01 mmol), intermediate 6 (0.103 g, 0.115 mmol), and intermediate 8 (0.077 g, 0.05 mmol) were added to a round-bottom flask. Anhydrous THF (1 mL) and anhydrous DMF (10 mL) were then added to dissolve the solid compound. The air was replaced under nitrogen protection. The reaction was carried out at 75°C for 24 h. After the reaction was completed, the reaction solution was cooled to room temperature and a small amount of water was added. The solution was then extracted with CHCl₃ (30 mL x 2). The lower organic layers were combined and washed with saturated brine (30 mL x 5). The organic layers were dried over anhydrous sodium sulfate and the solvent was evaporated. The crude product was separated and purified by column chromatography (methanol:chloroform = 1:90). 0.043 g of a yellow solid was obtained with a yield of 25%.

[0065] Target compound structure confirmation

[0066] The H NMR spectra of the target compounds were determined (e.g. Figure 1 ) and C NMR spectra (such as Figure 2 ), and then compare the measured data with the data simulated by Chemdraw software to determine that the target compound obtained is the target compound designed and synthesized by us.

[0067] The liquid crystal properties of target compound 9 were tested by polarizing optical microscopy (POM). The results showed that compound 9 is a liquid crystal with a wide temperature range, namely, the rising temperature range is Cr RT SmA 122℃ Iso and the cooling temperature range is 116℃ SmA RT Cr. We found that under the polarizing microscope, target compound 9 showed a black area ( Figure 3 a), similar to an isotropic liquid, which means that the orientation and arrangement of the molecules are perpendicular to the layer plane, and this texture is a typical feature of smectic liquid crystal compounds. The compound begins to show the SmA phase ( Figure 3 b), then the temperature was raised to 65 °C, and compound 9 showed a clearer SmA phase ( Figure 3 c), when compound 9 is heated to 122 °C, the SmA phase disappears and becomes an isotropic liquid; during the cooling process, the same SmA phase is also observed between 116 °C and RT ( Figure 3 (d)).

[0068] This triazole liquid crystal molecule has an alkoxy chain containing azobenzene at one end and a pillar[5]arene at the other end. The flexible chains of this compound overlap with each other, and the rigid cores are arranged in parallel in a shoulder-to-shoulder manner to form staggered layers, which are staggered and eventually present in the form of a bilayer phase, such as Figure 4 shown.

[0069] like Figure 5 As shown in Figure 2, target compound 9 is usually in a relatively stable trans configuration. Due to the π-π* electronic transition, it has a strong absorption peak at about 360nm. However, due to the n-π* electronic transition, a very weak absorption band appears near 455nm. Figure 5 As shown, the target molecule 9 is dissolved in dichloromethane and irradiated with ultraviolet light (wavelength of 365nm). As the irradiation time increases, the energy obtained by the compound increases, and its azobenzene chromophore gradually changes to the cis configuration. Accordingly, the molecule also changes from linear to curved. The absorption peak near 455nm corresponding to the n-π* electronic transition slowly increases, while the absorption peak near 360nm gradually weakens. After irradiating with ultraviolet light for 50s, the absorbance of compound 9 at 360nm no longer changes substantially, which indicates that the cis-trans isomerism of this compound has reached equilibrium. Since the energy of the compound in the trans configuration is lower and more stable, the energy of the compound in the cis configuration is high and usually unstable, so the ultraviolet light is removed. Under visible light, compound 9 gradually changes from cis to trans again, and the absorbance near 360nm gradually increases again. After about 2.5min, the height of the target molecule absorption peak no longer increases substantially, and is roughly the same as the height when not irradiated with ultraviolet light. Obviously, the compound is completely in the trans form again. In summary, pillararene azo compound 9 also exhibits reversible photoresponsive properties in organic solvents.

[0070] The present invention uses p-nitrophenol and methyl gallate as raw materials to design and synthesize azide compounds, and synthesizes the required terminal alkyne of pillar[5]arene from p-diphenol. Finally, a pillar[5]arene liquid crystal compound is designed and synthesized using the Click reaction as the key step. This structure contains a 1,2,3-triazole core, with pillar[5]arene at one end and an alkoxy chain of an azo group at the other end. The target compound is separated and purified by column chromatography, and then its liquid crystal properties and photoresponse properties are studied. The research results show that the compound will show SmA phase regardless of whether the temperature is increased or decreased; under ultraviolet light and visible light irradiation, its absorbance gradually decreases and increases with time, while the molecular energy gradually increases and decreases, thereby causing cis-trans tautomerism.

[0071] Currently, research on pillararene liquid crystal compounds is relatively limited, and the liquid crystal phases that have been discovered are mostly smectic. This type of azobenzene macrocyclic oligomer, due to the presence of ether bonds, possesses a rich, flexible, long aliphatic chain. It exhibits a liquid crystal phase (SmA phase) over a wide temperature range, exhibits good photoresponsive behavior, and exhibits excellent film-forming properties, making it a novel photosensitive material with unlimited potential. Overall, research on this type of compound lays a good foundation for further exploration of new pillararene liquid crystal molecules.

[0072] The present invention is not limited to the above embodiments. Those skilled in the art will appreciate that various changes, modifications, substitutions and variations may be made to these embodiments without departing from the principles and purpose of the present invention. The scope of the present invention is defined by the claims and their equivalents.

Claims

1. A novel liquid crystal supramolecular compound, characterized in that: The structural formula is:

2. A method for preparing the novel liquid crystal supramolecular compound according to claim 1, characterized in that: Using p-nitrophenol as the starting material, the intermediate 1 is obtained under alkaline conditions; methyl gallate reacts with dodecyl bromide to obtain intermediate 2, intermediate 2 is reduced to obtain intermediate 3, intermediate 3 is chlorinated to obtain intermediate 4, intermediate 1 and intermediate 4 are reacted to obtain intermediate 5, intermediate 5 is reacted with propargyl bromide to obtain intermediate 6; 1,4-dioxyethyl bromide reacts with (CH2O) n The reaction generates intermediate 7, intermediate 7 reacts with sodium azide to generate intermediate 8, and intermediate 8 reacts with intermediate 6 to generate the target product; The reaction formula is:

3. The method for preparing the novel liquid crystal supramolecular compound according to claim 2, characterized in that: The synthesis of intermediate 1 is as follows: KOH and water are added to a reaction container, stirred under an ice bath condition until cooled to room temperature, p-nitrophenol is added, the reaction starts at 120°C, and after the temperature reaches 120°C, the temperature is heated to 200°C at a rate of 5°C / time until the reaction is complete. After the reaction is completed, the reaction is cooled to room temperature, water is added to the reaction container, the pH value of the solution is adjusted to 3-4 with dilute HCl, extraction is performed with ethyl acetate, the organic layer is dried, and evaporated to dryness under reduced pressure to obtain a yellow crude product, and the crude product is separated and purified by column chromatography to obtain intermediate 1.

4. The method for preparing the novel liquid crystal supramolecular compound according to claim 3, characterized in that: The synthesis of intermediate 2 is as follows: methyl gallate and K2CO3 are added to a reaction container, N,N-dimethylformamide is added as a solvent, and reflux reaction is carried out; dodecyl bromide is slowly added to the reaction solution, and the reaction is continued until the reaction is complete, the reaction solution is cooled to room temperature, water and ethyl acetate are added to extract the upper organic layer, the organic layer is washed with a saturated NaCl solution, dried over anhydrous sodium sulfate, the solvent is evaporated, and intermediate 2 is purified by column chromatography.

5. The method for preparing the novel liquid crystal supramolecular compound according to claim 4, characterized in that: The synthesis of intermediate 3 is as follows: THF and intermediate 2 are added to a flask, LiAlH4 is added under ice bath conditions, and the reaction is carried out at room temperature until the reaction is complete. Water is slowly added dropwise to the reaction solution under ice bath conditions, and a large amount of bubbles and white solids are observed to be generated. Then, dilute HCl is added until no bubbles are generated. The organic layer is extracted with dichloromethane, dried over anhydrous sodium sulfate, and then the solvent is evaporated to obtain intermediate 3.

6. The method for preparing the novel liquid crystal supramolecular compound according to claim 5, characterized in that: The synthesis of intermediate 4 is as follows: THF, DMF and intermediate 3 are added to a reaction container, stirred, thionyl chloride is added dropwise and reacted at room temperature until the reaction is complete, and the solvent is distilled off under reduced pressure to obtain intermediate 4.

7. The method for preparing the novel liquid crystal supramolecular compound according to claim 6, characterized in that: The synthesis of intermediate 5 is as follows: intermediate 4, intermediate 1, and K2CO3 are added to a reaction vessel, and then DMF is added until completely dissolved, refluxed until the reaction is completed, cooled to room temperature, water is added, and suction filtered. The obtained product is dissolved in ethyl acetate, dried over anhydrous sodium sulfate, and evaporated to dryness under reduced pressure, and purified by column chromatography to obtain intermediate 5.

8. The method for preparing the novel liquid crystal supramolecular compound according to claim 7, characterized in that: The synthesis of intermediate 6 is as follows: potassium carbonate, intermediate 5, solvent CH3CN and propargyl bromide are added to a reaction container, reflux reaction is carried out until the reaction is complete, the reaction solution is cooled to room temperature, the solvent is evaporated under reduced pressure, and then the organic layer is extracted with water and dichloromethane, washed with NaOH aqueous solution and saturated brine and then dried, the solvent is evaporated under reduced pressure, and the crude product is separated and purified by column chromatography to obtain intermediate 6.

9. The method for preparing the novel liquid crystal supramolecular compound according to claim 8, characterized in that: The synthesis of intermediate 7 is as follows: (CH2O) n , 1,4-dioxoethyl bromide was added to the reaction vessel; chloroform was added to dissolve, boron trifluoride ether was added dropwise, and the reaction was carried out at room temperature until the reaction was completed, water was added, and CH2Cl2 was extracted. The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The intermediate 7 was separated and purified by column chromatography.

10. The method for preparing the novel liquid crystal supramolecular compound according to claim 9, characterized in that: The synthesis of intermediate 8 is as follows: intermediate 7, NaN3, KI and DMF are added to a reaction vessel, dissolved, refluxed to react until the reaction is complete, cooled to room temperature, added with water, extracted with CH2Cl2, the organic layer is washed with saturated sodium chloride, dried with anhydrous sodium sulfate, and the solvent is evaporated to obtain intermediate 8; The method for preparing the novel liquid crystal supramolecular compound according to claim 9, characterized in that: The synthesis of intermediate 9 is as follows: cuprous iodide, intermediate 6 and intermediate 8 are added to a reaction container, anhydrous THF and anhydrous DMF are added to dissolve the solid compound, N2 is protected, the reaction is completed at 75°C, and the product is cooled to room temperature; water is added, and then extracted with CHCl3, the organic layer is washed with saturated brine, dried with anhydrous sodium sulfate, and then the solvent is evaporated, and the product is separated and purified by column chromatography.

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