Supramolecular liquid crystal compound and preparation method thereof
By synthesizing liquid crystal compounds containing columnar[5] aromatic azobenzenetriazole, the problems of photoresponsiveness and stability of liquid crystal materials were solved, and SmA phase and reversible photoresponsiveness were realized over a wide temperature range, which is suitable for photoelectric molecular switches.
Patent Information
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- YANGTZE NORMAL UNIVERSITY
- Filing Date
- 2026-02-03
- Publication Date
- 2026-05-12
AI Technical Summary
Existing liquid crystal materials have shortcomings in terms of photoresponsiveness and stability, especially the photomodulation performance of smectic liquid crystals needs to be improved.
A novel liquid crystal supramolecular compound was designed and synthesized. Using p-nitrophenol and methyl gallate as starting materials, a series of chemical reactions were carried out to synthesize a liquid crystal compound containing columnar aromatic azotriazole [5]. The Click reaction was used to form a stoichiometric (SmA) structure with good photoresponsiveness.
A stable SmA phase of liquid crystal compound was achieved over a wide temperature range, exhibiting good photoresponse behavior and reversible photophysical properties, making it suitable for photoelectric molecular switches.
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Figure CN122010853A_ABST
Abstract
Description
Technical Field
[0001] This invention relates to the field of new materials technology, specifically to a supramolecular liquid crystal compound and its preparation method. Background Technology
[0002] Liquid crystals are soft substances that lie between solids and liquids. They not only maintain the anisotropy of solids but also possess the continuity and fluidity of liquids. Since their discovery, liquid crystal materials have been widely used in various fields, such as home appliances, industrial equipment, and GPS navigators; it can be said that liquid crystals are ubiquitous.
[0003] As a liquid crystal photosensitive material, azobenzene liquid crystal molecules based on columnar[5]arenes are very attractive. Conventional polymer photosensitive materials have indeterminate compositions, and simple azobenzene derivatives undergo severe hydrogen polymerization, while columnar[5]arene azobenzene liquid crystal molecules overcome these drawbacks. The tubular columnar[5]arene macrocyclic skeleton provides sufficient free space for azobenzene to achieve reversible photoisomerization, thus exhibiting excellent phototriggered modulation of surface free energy, wettability, and photoinduced orientation.
[0004] To date, liquid crystals can be classified based on several criteria. Due to differences in molecular shape, they can be divided into three categories: banana-shaped, rod-shaped, and disc-shaped liquid crystals. Based on differences in molecular weight, they can be divided into two main categories: liquid crystal polymers and small-molecule liquid crystals. Due to different compositional conditions and components, liquid crystals can be classified into lyotropic liquid crystals and thermotropic liquid crystals. Thermotropic liquid crystals exhibit properties that change with temperature and are pure substances; while lyotropic liquid crystals, on the other hand, have properties that change under different solvents and concentrations and are mixtures.
[0005] Thermotropic liquid crystals can be divided into three main categories: nematic phases, cholesteric phases, and smectic phases, with smectic A and C being the most common. Smectic liquid crystal molecules are arranged in layers, with their main axes parallel to each other within the layers. The orientation of SmA phase liquid crystal compounds is perpendicular to the layer, while the orientation of SmC phase liquid crystal axes is tilted towards the layer. Molecules can move back and forth and left and right, but cannot move between upper and lower layers. Because smectic phases are ordered, they typically appear at low temperatures. Nematic phase molecules maintain a basically parallel main axis, but compared to smectic phases, their center of mass is more disordered, resulting in considerable fluidity. Most cholesteric liquid crystal molecules are derivatives of cholesterol, with a helical structure and high optical activity. In fact, these molecules are a special state of the nematic phase. Besides these, there are also blue phases, columnar phases, and three-dimensional cubic phases.
[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] To address the aforementioned technical problems, the first objective of this invention is to provide a liquid crystal molecule compound, and the second objective is to provide a method for preparing the compound. This compound possesses a slab phase (SmA) and exhibits excellent photoresponse behavior.
[0008] To achieve the first objective mentioned above, this invention provides a novel liquid crystal supramolecular compound with the following structural formula: .
[0009] The second objective of this invention is achieved as follows: A method for preparing the novel liquid crystal supramolecular compound, characterized in that: p-nitrophenol is used 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-dioxoethyl 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: .
[0010] In the above scheme: the synthesis of intermediate 1 is as follows: KOH and water are added to the reaction vessel, stirred under ice bath conditions until cooled to room temperature, p-nitrophenol is added, the reaction starts at 120 °C, after the temperature reaches 120 °C, it is heated to 200 °C at 5 °C / time until the reaction is complete, after the reaction is completed, 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, extracted with ethyl acetate, the organic layer is dried, evaporated under reduced pressure to obtain a yellow crude product, the crude product is separated and purified by column chromatography to obtain intermediate 1.
[0011] 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 saturated NaCl solution, dried with anhydrous sodium sulfate, the solvent is evaporated, and intermediate 2 is purified by column chromatography.
[0012] In the above scheme, the synthesis of intermediate 3 is as follows: THF and intermediate 2 are added to a flask, and LiAlH4 is added under ice bath conditions. 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. A large number of bubbles and white solids are observed to be produced. Then dilute HCl is added until no more bubbles are produced. The organic layer is extracted with dichloromethane, dried with anhydrous sodium sulfate, and the solvent is evaporated to obtain intermediate 3.
[0013] 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 removed by vacuum distillation to obtain intermediate 4.
[0014] In the above scheme, the synthesis of intermediate 5 is as follows: intermediate 4, intermediate 1, and K2CO3 are added to a reaction vessel, then DMF is added until completely dissolved, the reaction is refluxed until the reaction is completed, cooled to room temperature, water is added, and the mixture is filtered. The product obtained is dissolved in ethyl acetate, dried with anhydrous sodium sulfate, and then evaporated under reduced pressure. Intermediate 5 is purified by column chromatography.
[0015] In the above scheme, intermediate 6 is synthesized by adding potassium carbonate, intermediate 5, solvent CH3CN and propargyl bromide to a reaction vessel, refluxing until the reaction is complete, cooling the reaction solution to room temperature, evaporating the solvent under reduced pressure, extracting the organic layer with water and dichloromethane, washing with NaOH aqueous solution and saturated brine, drying, evaporating the solvent under reduced pressure, and separating and purifying the crude product by column chromatography to obtain intermediate 6.
[0016] In the above scheme: the synthesis of intermediate 7 is achieved by adding (CH2O) n 1,4-Dioxoethyl bromide was added to the reaction vessel; chloroform was added to dissolve it, boron trifluoride ether was added dropwise, and the reaction was carried out at room temperature until the reaction was completed. Water was added, and the mixture was extracted with CH2Cl2. The organic layer was dried with anhydrous sodium sulfate and the solvent was evaporated under reduced pressure. The intermediate 7 was obtained by column chromatography.
[0017] 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, water is added, 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.
[0018] 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 compound, N2 protection is applied, the reaction is completed at 75 ℃, and then cooled to room temperature; water is added, and then CHCl3 is used for extraction. The organic layer is washed with saturated brine, dried with anhydrous sodium sulfate, and the solvent is evaporated. The product is obtained by separation and purification by column chromatography.
[0019] Beneficial effects: This paper designs and synthesizes azide compounds using p-nitrophenol and methyl gallate as raw materials, synthesizes the required columnar [5] aromatic terminal alkynes starting from p-diphenol, and finally designs and synthesizes a new azobenzenetriazole liquid crystal compound based on columnar [5] aromatics using the Click reaction as the core. The liquid crystal properties and photoresponse properties of this compound are mainly tested by POM and UV methods. This compound can form a smectic phase (SmA). Its photoresponse properties are studied by ultraviolet spectroscopy. The results show that the compound has a smectic phase (SmA), good photoresponse behavior and reversible photophysical properties, and is expected to be used for photoelectric molecular switches. Attached Figure Description
[0020] Figure 1 The hydrogen nuclear magnetic resonance spectrum of the target product of this invention.
[0021] Figure 2 The nuclear magnetic resonance carbon spectrum of the target product of this invention.
[0022] Figure 3 POM texture diagrams 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.
[0023] Figure 4 This is a schematic diagram of the formation of the layered phase (SmA) of the target product of the triazole class in this invention.
[0024] Figure 5 For target compound 9 in dichloromethane (c = 10 -5 UV absorption spectra in M): (a) irradiated with 365 nm ultraviolet light, (b) irradiated with visible light. Detailed Implementation
[0025] The present invention will be further illustrated below through examples: Example 1 Synthesis of Intermediate 1 KOH (30 g, 534 mmol) and water (6 mL) were added to a round-bottom flask and stirred in an ice bath until cooled to room temperature. Then, p-nitrophenol (4.7 g, 33.8 mmol) was added. The reaction was initiated at 120 °C (and then heated to 200 °C in increments of 5 °C) for 4 h. Thin-layer chromatography was used to confirm the reaction was complete. After the reaction, the product was allowed to cool to room temperature, and a suitable amount of water was added to the round-bottom flask before being poured into a beaker. The pH of the solution was adjusted to approximately 3-4 with dilute HCl (2 M), and then extracted with ethyl acetate (30 mL × 3 times). The extracted organic layers were combined, dried, and evaporated under reduced pressure to obtain a yellow crude product. The crude product was purified by column chromatography (petroleum ether:ethyl acetate = 2:1). 1.4 g of an orange-yellow solid was obtained, with a yield of 25%.
[0026] Example 2 Synthesis of intermediate 2: 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 the solvent. The mixture was refluxed at 95 °C for 0.5 h. Subsequently, C₂CO₃ was slowly added to the reaction solution. 12 H 25 Br (bromododecyl) (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 then the reaction solution was cooled to room temperature. Water (10 mL) and ethyl acetate (30 mL) were added to a separatory funnel to extract the upper organic layer, which was then washed with saturated NaCl (30 mL × 5 times) and dried with anhydrous sodium sulfate. The solvent was evaporated, and the crude product was purified by column chromatography (petroleum ether:ethyl acetate = 60:1). Finally, 4.0 g of white solid was obtained, and the yield was calculated to be 92%.
[0027] Example 3 Synthesis of intermediate 3: 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 complete, water was slowly added dropwise to the reaction solution under ice bath conditions, and a large number of bubbles and a white solid were observed to be produced. Then, dilute HCl (2 M) was added until no more bubbles were produced. The organic layer was extracted with CH2Cl2 (30 mL × 3 times), dried with anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. 2.8 g of white solid product was obtained, and the yield was calculated to be 93%.
[0028] Example 4 Synthesis of intermediate 4: 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. Then, thionyl chloride (0.3 mL, 4.8 mmol) was added dropwise and the mixture was reacted at room temperature for 12 h. After the reaction was complete, the solvent in the solution was removed by vacuum distillation at approximately 60 °C. A white solid of 2.5 g was obtained, with a yield of 90%.
[0029] Example 5 Synthesis of intermediate 5: 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 complete, the reaction solution in the flask was cooled to room temperature, and water was added directly to the flask. The mixture was then filtered, and 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 purified by column chromatography (ethyl acetate: petroleum ether = 1:5). 0.74 g of a yellow solid product was obtained, with a calculated yield of 20%.
[0030] Example 6 Synthesis of intermediate 6: 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 the addition of solvent 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 completed, the reaction solution was cooled to room temperature, and the solvent was directly evaporated under reduced pressure. The organic layer was then extracted with water and CH₂Cl₂ (20 mL × 3 times), and gradually washed with NaOH aqueous solution (2.5 M) and saturated brine before drying. CH₂Cl₂ was evaporated under reduced pressure, and the crude product was separated and purified by column chromatography (petroleum ether: ethyl acetate = 10:1). Finally, 0.11 mg of the yellow product was obtained, with a yield of 18%.
[0031] Example 7 Synthesis of intermediate 7: 7 (CH2O) n 750 mg of 1,4-dioxoethyl bromide (4 g, 13.5 mmol) was added to a round-bottom flask; CHCl3 (75 mL) was added as solvent to dissolve the bromide, and boron trifluoride diethyl ether (3 mL, 2.67 mmol) was added dropwise. The mixture was reacted at room temperature for 3 h. After the reaction was complete, water was added to the round-bottom flask, and the mixture was extracted with CH2Cl2 (20 mL × 3 times) in a separatory funnel. The resulting organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. Finally, the white crude product was separated and purified by column chromatography (petroleum ether: dichloromethane = 1:1). 0.65 g of white solid was obtained, with a yield of 15.56%. Example 8 Synthesis of intermediate 8: 7 8 Intermediate 7 (0.11 g, 0.057 mmol), NaN3 (0.056 g, 0.861 mmol), KI (0.1 g, 0.6 mmol), and DMF were added to a round-bottom flask and dissolved. The mixture was refluxed at 95 °C for 12 h. After confirming the reaction was complete, the mixture was cooled to room temperature, and 15 mL of water was added. The mixture was extracted with CH2Cl2 (30 mL × 3 times). The lower organic layer was then extracted with saturated NaCl (20 mL × 2 times), and the organic phase was dried over anhydrous Na2SO4. The solvent was evaporated to obtain intermediate 8, a white solid of 0.085 g, with a yield of 96%.
[0032] Example 9 Synthesis of target product 9: 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, followed by the addition of anhydrous THF (1 mL) and anhydrous DMF (10 mL) to dissolve the solid compound. The mixture was then purged with air under N2 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. A small amount of water was added to the reaction solution, followed by extraction with CHCl3 (30 mL × 2 times). The lower organic layers were combined and washed with saturated brine (30 mL × 5 times). The organic layers were dried with anhydrous sodium sulfate, and the solvent was evaporated. Finally, 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%.
[0033] Target compound structure confirmed The proton NMR spectrum of the target compound was determined (e.g., Figure 1 ) and nuclear magnetic resonance carbon spectroscopy (such as Figure 2 Then, the measured data was compared with the data simulated by Chemdraw software to confirm that the obtained target compound was the target compound we designed and synthesized.
[0034] The liquid crystal properties of target compound 9 were examined using polarized optical microscopy (POM). The results showed that compound 9 is a liquid crystal with a wide temperature range: the heating range is Cr RT SmA 122 °C Iso, and the cooling range is 116 °C SmA RT Cr. We found that under polarized light microscopy, target compound 9 exhibited a black region (…). Figure 3 The structure (a) resembles an isotropic liquid, indicating that the molecular orientation and arrangement are perpendicular to the layer plane, and this texture is typical of lamellae liquid crystal compounds. The compound begins to exhibit the SmA phase at room temperature (…). Figure 3 Compound 9 (b) was then heated to 65 °C, and showed a clearer SmA phase (b). Figure 3 (c) When compound 9 is heated to 122°C, this SmA phase disappears, and it becomes an isotropic liquid; during the cooling process, the same SmA phase is also observed between 116°C and RT. Figure 3 (d)
[0035] This triazole liquid crystal molecule has an alkoxy chain containing azobenzene at one end and a columnar aromatic hydrocarbon at the other end [5]. The flexible chains of this compound overlap each other, and the rigid cores are arranged side by side in parallel to form an interlaced layer. The interlaced arrangement eventually presents itself in a bilayer phase, such as Figure 4 As shown.
[0036] like Figure 5 As shown, target compound 9 is usually in a relatively stable trans configuration, due to π-π Electronic transitions exhibit a strong absorption peak at approximately 360 nm. However, due to n-π... Electron transitions occur, resulting in a very weak absorption band around 455 nm. For example... Figure 5 As shown, target molecule 9 was dissolved in dichloromethane and irradiated with ultraviolet light (wavelength 365 nm). As the irradiation time increased, the compound gained more energy, and its azobenzene chromophore gradually changed to a cis configuration. Correspondingly, the molecule changed from a linear to a bent configuration, n-π The absorption peak near 455 nm corresponding to the electronic transition slowly increases, while the absorption peak near 360 nm gradually decreases. After irradiation with a UV lamp for 50 s, the absorbance of compound 9 at 360 nm remains essentially unchanged, indicating that the cis-trans isomerism of this molecule has reached equilibrium. Since the trans configuration is lower in energy and more stable, while the cis configuration is higher in energy and generally unstable, the UV lamp was removed, and under visible light irradiation, compound 9 gradually changed from the cis to the trans configuration again, and the absorbance near 360 nm gradually increased. After about 2.5 min, the height of the target molecule's absorption peak essentially stopped increasing and was roughly the same as when it was not irradiated with a UV lamp. Obviously, the compound is now completely in the trans configuration again. In summary, the columnar aromatic azo compound 9 also exhibits reversible photoresponsive properties in organic solvents.
[0037] This invention designs and synthesizes azide compounds using p-nitrophenol and methyl gallate as raw materials. Starting from p-diphenol, the desired columnar [5] aromatic terminal alkyne is synthesized. Finally, a columnar aromatic 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 the columnar [5] aromatic hydrocarbon at one end of the core and the other end of the core connected by an alkoxy chain of an azo group. The target compound is purified by column chromatography, and its liquid crystal properties and photoresponse properties are then studied. The results show that the compound exhibits the SmA phase regardless of whether the temperature is increased or decreased. Under ultraviolet and visible light irradiation, its absorbance gradually decreases and increases with time, while the molecular energy gradually increases and decreases, thus undergoing cis-trans tautomerism.
[0038] Currently, research on columnar aromatic liquid crystal compounds is relatively limited, and most of the discovered liquid crystal phases belong to the lamellae phase. These azobenzene macrocyclic oligomers possess abundant flexible long aliphatic chains due to the presence of ether bonds, exhibiting a liquid crystal phase (SmA phase) over a wide temperature range. They exhibit good photoresponse behavior and excellent film-forming properties, making them a novel and highly promising photosensitive material. In conclusion, research on these compounds lays a solid foundation for further exploration of novel columnar aromatic liquid crystal molecules.
[0039] This invention is not limited to the above embodiments. Those skilled in the art will understand that various changes, modifications, substitutions and variations can be made to these embodiments without departing from the principles and spirit of this invention. The scope of this 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: Starting with p-nitrophenol, intermediate 1 was obtained by reacting under alkaline conditions; methyl gallate reacted with dodecyl bromide to obtain intermediate 2, intermediate 2 was reduced to obtain intermediate 3, intermediate 3 was chlorinated to obtain intermediate 4, intermediate 1 and intermediate 4 reacted to obtain intermediate 5, intermediate 5 reacted with propargyl bromide to obtain intermediate 6; 1,4-dioxoethyl bromide reacted 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 was carried out as follows: KOH and water were added to a reaction vessel, and the mixture was stirred under ice bath conditions until it cooled to room temperature. p-Nitrophenol was then added, and the reaction was started at 120 °C. After the temperature reached 120 °C, the temperature was heated to 200 °C at 5 °C per cycle until the reaction was complete. After the reaction was completed, the mixture was cooled to room temperature, water was added to the reaction vessel, and the pH of the solution was adjusted to 3-4 with dilute HCl. The solution was extracted with ethyl acetate, the organic layer was dried, and the product was evaporated under reduced pressure to obtain a yellow crude product. The crude product was 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 was carried out by adding methyl gallate and K2CO3 into a reaction vessel, adding N,N-dimethylformamide as a solvent, and refluxing the mixture; slowly adding dodecyl bromo to the reaction solution and continuing the reaction until the reaction was complete; cooling the reaction solution to room temperature, adding water and ethyl acetate to extract the upper organic layer, washing the organic layer with saturated NaCl solution, drying with anhydrous sodium sulfate, evaporating the solvent, and purifying it by column chromatography to obtain intermediate 2.
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, and LiAlH4 is added under ice bath conditions. 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. A large number of bubbles and white solids are observed to be produced. Then dilute HCl is added until no more bubbles are produced. The organic layer is extracted with dichloromethane, dried with anhydrous sodium sulfate, and 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 vessel, stirred, thionyl chloride is added dropwise and reacted at room temperature until the reaction is complete, and the solvent is removed by vacuum distillation 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 was carried out by adding intermediate 4, intermediate 1, and K2CO3 into a reaction vessel, then adding DMF until completely dissolved, refluxing the reaction until the end of the reaction, cooling to room temperature, adding water, filtering, dissolving the product in ethyl acetate, drying with anhydrous sodium sulfate, evaporating under reduced pressure, and purifying 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 vessel and the reaction is refluxed until complete. The reaction solution is cooled to room temperature, the solvent is evaporated under reduced pressure, the organic layer is extracted with water and dichloromethane, washed with NaOH aqueous solution and saturated brine, dried, and the solvent is evaporated under reduced pressure. 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 involves adding (CH2O). n 1,4-Dioxoethyl bromide was added to the reaction vessel; chloroform was added to dissolve it, boron trifluoride ether was added dropwise, and the reaction was carried out at room temperature until the reaction was completed. Water was added, and the mixture was extracted with CH2Cl2. The organic layer was dried with anhydrous sodium sulfate and the solvent was evaporated under reduced pressure. The intermediate 7 was obtained 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 was carried out by adding intermediate 7, NaN3, KI, and DMF to a reaction vessel, dissolving them, refluxing the reaction until complete, cooling to room temperature, adding water, extracting with CH2Cl2, washing the organic layer with saturated sodium chloride, drying with anhydrous sodium sulfate, and evaporating the solvent to obtain the 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 vessel, anhydrous THF and anhydrous DMF are added to dissolve the solid compound, N2 protection is applied, the reaction is completed at 75 °C, and then cooled to room temperature; water is added, and then the mixture is extracted with CHCl3. The organic layer is washed with saturated brine, dried with anhydrous sodium sulfate, and the solvent is evaporated. The product is then separated and purified by column chromatography.