Chiral binaphthol-cyanostilbene compound as well as preparation method and application thereof
By introducing chiral R-BINOL units and cyanostilbene groups into liquid crystal molecules, R-BIN-DCyn compounds were prepared, solving the problem of insufficient luminescence in the aggregated state of chiral fluorescent liquid crystal materials. This resulted in efficient circularly polarized luminescence and high fluorescence quantum yield, making them suitable for organic light-emitting diodes and chiral fluorescent sensors.
Patent Information
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- BENGBU COLLEGE
- Filing Date
- 2025-12-29
- Publication Date
- 2026-05-12
Smart Images
Figure CN122010779A_ABST
Abstract
Description
Technical Field
[0001] This invention relates to the field of chiral aggregation-induced emission liquid crystal materials technology, specifically to a chiral binaphthol-cyanostilbene compound and its preparation method and application. Background Technology
[0002] Liquid crystals (LCs) are a special type of self-assembling medium, widely used in field-effect crystals, optical sensing materials, organic light-emitting diodes (OLEDs), and organic photovoltaic cells due to their unique π-π stacking structure and the rapid transport of charge carriers along the columnar axis. High-fluorescence liquid crystals, in particular, effectively combine inherent luminescence properties with molecular self-assembly characteristics, giving them advantages in simplified device design, low power consumption, high brightness, and high contrast. However, most fluorescent liquid crystal molecules are prone to aggregation-induced quenching (ACQ) in their aggregated state, suppressing fluorescence emission. Furthermore, the intermolecular π-π stacking hinders the formation of the liquid crystal phase, leading to the formation of intermediate phase coatings or linear media.
[0003] In 2001, Tang Benzhong's team first observed aggregation-induced emission (AIE) in 1-methyl-1,2,3,4,5-pentaphenylthiophene (MPPS) molecules. This research effectively solved the ACQ problem of traditional fluorescent materials and broadened the application of this type of molecule in liquid crystals, circularly polarized light emission, and other fields. Based on this, various AIE molecules have been constructed into highly efficient fluorescent liquid crystal materials. For example, cyanostilbene derivatives are highly favored due to their photostability, mechanical fluorination, and AIE performance. However, the design and synthesis of liquid crystal molecules with luminescent properties still face significant challenges. First, it is difficult to maintain the original liquid crystal properties after introducing functional luminescent groups into the liquid crystal molecule structure. Second, most compounds obtained by linking luminescent groups to liquid crystal molecules only emit strong light in dilute solutions, and the original AIE properties are no longer retained.
[0004] Considering that cyanostilbene is a type of highly fluorescent liquid crystal building block, introducing chiral R-1,1'-bi-2-naphthol (R-BINOL) units into its structure can effectively improve the Φ in the aggregated state or solid state of chiral luminescent liquid crystal molecules. F Furthermore, the highly ordered helical aggregate structure can enhance the intrinsic circularly polarized emission (CPL) performance of molecules. In R-BINOL molecules, the restricted rotation of the two naphthalenes around the C2 symmetry axis results in a stable chiral structure and high chiral induction; therefore, R-BINOL and its derivatives have gradually become ideal chiral sources for constructing CPL materials. Related studies have shown that the fluorescence quantum yield (Φ...) F ) and luminescence asymmetry factor (g lumThe gamma value is a key parameter for evaluating the practical application value of CPL materials. The chiral optical properties of CPL materials are also closely related to their aggregated structure; the ordered helical aggregated structure of molecules helps to improve gamma. lum However, chiral luminescent molecules struggle to form highly ordered helical structures in the dispersed state, resulting in weak CPL signals or even a lack of chiral optical response. In other words, CPL materials cannot simultaneously possess large g values in good solutions. lum Value and height Φ F .
[0005] According to literature reports, the g of chiral liquid crystal CPL materials lum The values are generally higher than those of other types of CPL materials. If the inherent AIE properties of cyanobrythril aggregates and the advantages of liquid crystal characteristics can be combined, it is hoped that a material with strong fluorescence and large g-values can be prepared. lum Value and height Φ F Chiral liquid crystal materials. Summary of the Invention
[0006] The technical problem to be solved by this invention is to provide a chiral binaphthol-cyanostilbene compound and its preparation method. This compound has AIE properties, liquid crystal properties, and circularly polarized light emission properties. It can still emit light efficiently after forming liquid crystal phase aggregates, overcoming the aggregation-induced quenching phenomenon that occurs in traditional light-emitting materials in the aggregated state. This provides a new idea for the design and synthesis of novel chiral aggregation-induced light emission liquid crystal materials.
[0007] The technical problem to be solved by this invention is achieved by the following technical solution:
[0008] One objective of this invention is to provide a chiral binaphthol-cyanostilbene compound, abbreviated as R-BIN-DCyn, with the following structural formula:
[0009]
[0010] Where n = 4~16.
[0011] A second objective of this invention is to provide a method for preparing the chiral binaphthol-cyanostilbene compound, comprising the following steps:
[0012] (1) 4-hydroxyphenylacetonitrile reacts with terephthalaldehyde via a Knoevenagel condensation reaction to give intermediate 1;
[0013]
[0014] (2) R-6,6'-dihalo-1,1'-bi-2-naphthol undergoes a Suzuki coupling reaction with 4-ether phenylboronic acid to give intermediate 2;
[0015]
[0016] (3) Intermediate 2 undergoes a substitution reaction with 1-halododecane to give intermediate 3;
[0017]
[0018] (4) Intermediate 3 undergoes a substitution reaction with 1,4-dihalobutane to give intermediate 4;
[0019]
[0020] (5) Intermediate 1 and intermediate 4 undergo a substitution reaction to give R-BIN-DCyn;
[0021]
[0022] Where n = 4~16, and R is one of F, Cl, or Br.
[0023] Furthermore, the molar ratio of 4-hydroxyphenylacetonitrile to terephthalaldehyde is (2~4):1.
[0024] Furthermore, the Knoevenagel condensation reaction is carried out under the action of a base. Even further, the base includes, but is not limited to, at least one of sodium hydroxide, pyridine, piperidine, and potassium tert-butoxide.
[0025] Furthermore, the reaction temperature of the Knoevenagel condensation reaction is 50~85℃.
[0026] Furthermore, the molar ratio of R-6,6'-dihalo-1,1'-bi-2-naphthol to 4-etherylphenylboronic acid is 1:(2.5~4.5).
[0027] Furthermore, the Suzuki coupling reaction is carried out in the presence of a base and a palladium catalyst. Even further, the base includes, but is not limited to, at least one selected from potassium acetate, potassium carbonate, sodium acetate, sodium carbonate, and magnesium carbonate.
[0028] Furthermore, the reaction temperature of the Suzuki coupling reaction is 100~150℃.
[0029] Furthermore, the molar ratio of intermediate 2 to 1-halododecane is (1.2~1.8):1.
[0030] Furthermore, the molar ratio of intermediate 3 to 1,4-dihalobutane is (1.5~3):1.
[0031] Furthermore, the molar ratio of intermediate 1 to intermediate 4 is 1:(3~5).
[0032] Furthermore, the substitution reaction is carried out in the presence of an acid-binding agent, which includes, but is not limited to, at least one of potassium carbonate, sodium sulfate, potassium iodide, potassium bromide, sodium iodide, sodium carbonate, sodium acetate, pyridine, and triethylamine.
[0033] Furthermore, the reaction temperature of the substitution reaction is 70~95℃.
[0034] A third objective of this invention is to provide the use of the chiral binaphthol-cyanostilbene compound as a chiral aggregation-induced emission liquid crystal material.
[0035] A fourth objective of this invention is to provide the application of the chiral aggregation-induced emission liquid crystal material in organic light-emitting diodes and chiral fluorescent sensors.
[0036] The beneficial effects of this invention are:
[0037] 1. This invention synthesizes a novel chiral binaphthol-cyanostilbene compound and discovers its use as a chiral aggregation-induced emission liquid crystal material. This material organically combines chiral structure, aggregation-induced emission characteristics and liquid crystal ordering. While forming a liquid crystal phase, it can not only emit light efficiently, but also achieve circularly polarized emission, providing a new idea for the design of multifunctional luminescent materials.
[0038] 2. The preparation method provided by this invention has the characteristics of mild conditions, simple steps, and readily available raw materials, which meets the requirements of green synthesis, has a high yield, good process scalability and applicability, and is conducive to subsequent industrialization and promotion.
[0039] 3. The synthesis route provided by this invention has good structural tunability. By adjusting the core framework, chiral groups or liquid crystal groups, the optical, chiral and liquid crystal properties of the material can be systematically controlled to meet the application requirements of different devices.
[0040] 4. The chiral aggregation-induced emission liquid crystal material described in this invention can be used in organic electroluminescent diodes, and in particular provides a feasible material solution for the development of high-performance circularly polarized electroluminescent devices, with potential application prospects in 3D display, optical information storage and encryption and other fields. Attached Figure Description
[0041] Figure 1 The 1H NMR spectrum of intermediate 1 prepared in Example 1 of this invention;
[0042] Figure 2 The 1H NMR spectrum of intermediate 2 prepared in Example 2 of this invention;
[0043] Figure 3 The mass spectrum of intermediate 2 prepared in Example 2 of this invention;
[0044] Figure 4 The 1H NMR spectrum of intermediate 3 prepared in Example 3 of this invention;
[0045] Figure 5 The 1H NMR spectrum of intermediate 4 prepared in Example 4 of this invention;
[0046] Figure 6 The 1H NMR spectrum of compound R-BIN-DCyn prepared in Example 5 of this invention;
[0047] Figure 7 The carbon NMR spectrum of compound R-BIN-DCyn prepared in Example 5 of this invention;
[0048] Figure 8 The fluorescence spectra of compound R-BIN-DCyn prepared in Example 5 of this invention in THF / H2O mixed solvent at different water contents;
[0049] Figure 9 The fluorescence spectrum of compound R-BIN-DCyn prepared in Example 5 of this invention in the solid film state;
[0050] Figure 10 The image shows the POM of compound R-BIN-DCyn prepared in Example 5 of this invention in a liquid crystal phase.
[0051] Figure 11 The circularly polarized fluorescence spectrum of compound R-BIN-DCyn prepared in Example 5 of this invention is shown in solid film form. Detailed Implementation
[0052] To make the technical means, creative features, objectives and effects of this invention easier to understand, the invention will be further described below with reference to specific embodiments and illustrations.
[0053] Taking n=8 as an example, chiral binaphthol-cyanostilbene compounds were prepared and their structures were characterized and their properties were tested:
[0054] Example 1
[0055] Preparation of intermediate 1:
[0056]
[0057] Terephthalaldehyde (2.68 g, 20.0 mmol), p-hydroxyphenylacetonitrile (5.60 g, 42.1 mmol), sodium hydroxide (3.20 g, 80.0 mmol), and anhydrous ethanol (150 mL) were heated to reflux and stirred for 6 h. After the reaction was completed, dilute hydrochloric acid (100 mL, 1 M) was added to the reaction solution, followed by water (300 mL). The mixture was allowed to stand for 30 min, filtered, and the filter residue was dried to obtain a yellow solid, i.e., intermediate 1, with a yield of 89%. 1 HNMR (600 MHz, d6-DMSO) δ ppm :10.15 (s, 2H, Ar-OH), 7.97 (s, 4H, ArH), 7.86 (s, 2H, C=CH), 7.61 - 7.59 (m, 4H, ArH), 6.90 (d, J = 8.7 Hz, 4H, ArH). MALDI-TOF-MS (C 24 H 16 N₂O₂) [M+(Na / K)] + : Calcd found: m / z = 387.9990, 404.1261.
[0058] Example 2
[0059] Preparation of intermediate 2:
[0060]
[0061] (R)-6,6'-dibromo-1,1'-bi-2-naphthol (4.42 g, 10.0 mmol), 4-octyloxyphenylboronic acid (8.76 g, 35.0 mmol), tetrakis(triphenylphosphine)palladium (0.23 g, 0.2 mmol), and a saturated acetonitrile-sodium carbonate solution (4:1, 100 mL, v / v) were heated to 120 °C and stirred for 20 h. After the reaction was completed, the reaction solution was cooled to room temperature and extracted three times with a mixture of saturated sodium chloride solution (150 mL) and chloroform (30 mL). The organic phases were combined, the extractant was removed by concentration under reduced pressure, and the solution was purified by silica gel column chromatography (eluent: petroleum ether-dichloromethane, v / v). The eluent was removed by concentration under reduced pressure, dried over anhydrous sodium sulfate, and filtered to obtain a colorless viscous liquid, i.e., intermediate 2, with a yield of 87%. 1 H NMR (600 MHz, CDCl3) δ ppm:8.04 (d, J = 2.0 Hz, 2H, ArH), 8.01 (d, J = 8.9 Hz, 2H, ArH), 7.61 - 7.58 (m,4H, ArH), 7.56 - 7.54 (m, 2H, ArH), 7.40 (d, J = 8.9 Hz, 2H, ArH), 7.24 (d, J= 8.8 Hz, 2H, ArH), 7.01 - 6.98 (m, 4H, ArH), 5.14 (s, 2H, Ar-OH), 4.00 (t, J= 6.6 Hz, 4H, -OCH2-), 1.83 - 1.79 (m, 24H, -CH2-), 0.91 (t, J = 6.9 Hz, 6H, -CH3). HR-ESI-MS: m / z: [M] + Calcd for C 48 H 54 O4, 694.9560; Found: m / z [M+H] + ,695.4033.
[0062] Example 3
[0063] Preparation of intermediate 3:
[0064]
[0065] Intermediate 2 (3.75 g, 5.4 mmol), 1-bromododecane (2.01 g, 8.1 mmol), potassium carbonate (2.40 g, 17.4 mmol), and acetonitrile (40 mL) were heated to reflux and stirred for 15 h. After the reaction was completed, the reaction solution was cooled to room temperature, the solvent was removed by vacuum distillation, and then extracted three times with a mixed solution of water (400 mL) and dichloromethane (60 mL). The organic phases were combined, the extractant was removed by vacuum concentration, and the solution was purified by silica gel column chromatography (eluent was n-hexane-ethyl acetate in a volume ratio of 10:1). The eluent was removed by vacuum concentration, dried over anhydrous sodium sulfate, and filtered to obtain a colorless viscous liquid, namely intermediate 3, with a yield of 85%. 1 H NMR (600 MHz, CDCl3) δ ppm: 8.02 (d, J = 9.0 Hz, 2H, ArH), 7.89 (dd, J =8.7, 2.8 Hz, 4H, ArH), 7.85 (d, J = 8.1 Hz, 2H, ArH), 7.47-7.44 (m, 2H, ArH), 7.39 - 7.33 (m, 2H, ArH), 7.29 (m, 4H, ArH), 7.22 - 7.18 (m, 4H, ArH), 7.06 (d, J = 8.5 Hz, 2H, ArH), 4.95 (s, 1H, Ar-OH), 4.01 - 3.95 (m, 6H, -OCH2-), 1.44 - 0.95 (m, 40H, -CH2-), 0.90 (t, J = 7.0 Hz, 9H, -CH3).
[0066] Example 4
[0067] Preparation of intermediate 4:
[0068]
[0069] Intermediate 3 (2.76 g, 3.2 mmol), 1,4-dibromobutane (1.38 g, 6.4 mmol), potassium carbonate (2.50 g, 18.1 mmol), and acetonitrile (50 mL) were heated to reflux and stirred for 13 h. After the reaction was completed, dilute hydrochloric acid (100 mL, 1 M) was added to the reaction solution, and the mixture was extracted three times with a mixture of chloroform (15 mL) and water (120 mL). The organic phases were combined, the extractant was removed by concentration under reduced pressure, and the mixture was purified by silica gel column chromatography (eluent was n-hexane-ethyl acetate with a volume ratio of 20:1). The eluent was removed by concentration under reduced pressure, dried over anhydrous sodium sulfate, and filtered to obtain a yellow liquid, namely intermediate 4, with a yield of 76%. 1 H NMR (600 MHz, CDCl3) δ ppm: 8.01-8.00 (m, 2H, ArH), 7.98 - 7.96 (m, 3H, ArH), 7.88 - 7.60 (m,3H, ArH), 7.59-7.43 (d, J = 8.2 Hz, 3H, ArH), 7.42-7.37 (dd, J = 15.0, 9.0Hz, 4H, ArH), 7.26-7.19 (m, 1H, ArH), 7.10-6.92 (d, J = 8.2 Hz, 4H, ArH), 4.36 - 3.43 (m, 8H, -OCH2-), 2.96 - 2.29 (m, 2H, -CH2Br), 1.82 - 0.96 (m, 44H,-CH2-), 0.89 (t, J = 6.9 Hz, 9H,-CH3). HR-ESI-MS: m / z Calcd for C 36 H 45 BrO2:996.2841; Found: 1019.24311.
[0070] Example 5
[0071] Preparation of compound R-BIN-DCyn:
[0072]
[0073] Intermediate 1 (0.29 g, 0.8 mmol), intermediate 4 (3.39 g, 3.4 mmol), and potassium carbonate (2.71 g, 19.6 mmol) were heated to reflux and stirred for 15 h. After the reaction was completed, the reaction solution was cooled to room temperature, and dilute hydrochloric acid (80 mL, 1 M) was added. The mixture was extracted three times with a mixture of dichloromethane (25 mL) and water (150 mL). The organic phases were combined, and the extractant was removed by concentration under reduced pressure. The solution was purified by silica gel column chromatography (eluent: dichloromethane-petroleum ether, v / cm). The eluent was removed by concentration under reduced pressure to give a yellow-green solid, namely compound R-BIN-Cyn, in 79% yield. FT-IR (KBr), v / cm -1 : 2181 (C=N), 1571 (C=O). 1 H NMR (600 MHz, CDCl3) δ ppm: 8.02 - 7.91 (m, 6H, ArH), 7.62 -7.56 (m, 4H, ArH), 7.48 - 7.42 (m, 6H, ArH), 7.31 (d, J = 8.7 Hz, 1H, ArH),7.27 - 7.25 (d, J = 8.8 Hz, 2H, ArH), 7.01 - 6.95 (m, 4H, ArH), 6.99-6.94(dd, J = 15.1, 8.8 Hz, 2H, ArH), 4.11 - 4.03 (m, 1H, -OCH2-), 4.02 - 3.97 (m,4H, -OCH2-), 3.97 - 3.89 (m, 3H, -OCH2-), 3.47 - 3.33 (m, 2H, -OCH2-), 1.85 -0.85 (m, 54H, -CH2- and -CH3). 13 C NMR (151 MHz, CDCl3) δ ppm : 160.07, 158.65,158.62, 158.59, 154.59, 154.36, 138.11, 136.03, 135.74, 135.36, 133.47,133.25, 133.07, 133.04, 130.10, 129.83, 129.57, 129.51, 129.48, 129.40,129.36, 129.09, 128.12, 128.08, 127.44, 127.24, 126.21, 126.09, 126.02,125.75, 125.68, 124.94, 124.88, 121.02, 120.50, 118.00, 116.62, 116.29,115.09, 114.87, 114.81, 112.24, 69.86, 69.57, 68.11, 68.09, 67.19, 33.55,31.97, 31.85, 31.73, 29.71, 29.69, 29.59, 29.55, 29.44, 29.43, 29.41, 29.34,29.28, 29.21, 26.10, 26.08, 25.71, 25.47, 22.74, 22.69, 14.18, 14.14. HRMS(ESI) (C 150 H 180 N2O 10): Calculated for [M] + : 2170.3692, Found: 2193.9971 [M+H+Na] + Anal. Calcd. for C 150 H 180 N2O 10 : C, 82.98; H, 8.36; N, 1.29. Found: C, 83.04; H, 8.29; N, 1.33.
[0074] Example 6
[0075] The aggregation-induced emission properties of R-BIN-DCyn prepared in Example 5 were tested:
[0076] R-BIN-DCyn was dissolved in tetrahydrofuran (THF) to prepare a solution with a concentration of 1×10⁻⁶. -3 The stock solution of M was then diluted to 1×10⁻⁶. -5 M. Subsequently, H2O-THF mixed solutions with water content (volume fraction) ranging from 0% to 95% were prepared by adding different proportions of water (H2O). Fluorescence emission spectra were measured under an excitation wavelength of 340 nm (corresponding to the absorption peak of cyano-substituted stilbene). Figure 8 ).from Figure 8 It can be seen that when the water content is below 50%, the fluorescence emission intensity gradually decreases with increasing water content in the mixed solution, while the emission peak undergoes a red shift. This change reflects a significant distortion of intramolecular charge transfer effect. During the process of enhanced solvent polarity, molecules become polarized and tend to become planarized, intensifying intermolecular π-π stacking interactions and forming a certain degree of aggregation, thus leading to weakened fluorescence. However, when the water content exceeds 60%, the fluorescence intensity of the system increases sharply, exhibiting typical aggregation-induced emission characteristics.
[0077] A dichloromethane solution of R-BIN-DCyn was uniformly dropped onto a quartz plate using a drop-coating method. The solvent was evaporated at room temperature to obtain a solid film. The fluorescence emission spectrum of the solid film was measured at an excitation wavelength of 340 nm. Figure 9 ).from Figure 9 As can be seen, R-BIN-DCyn exhibits strong fluorescence in the solid film state, with the maximum fluorescence emission peak concentrated in the 480–520 nm range. Compared to the fluorescence spectrum in solution, the maximum fluorescence emission peak of R-BIN-DCyn in the solid film state shows a sustained redshift. In the solid state, the torsional motion of molecules is restricted, and the molecules are essentially in a planar conformation, which is the main reason for the redshift in the solid-state fluorescence spectrum.
[0078] The results above show that R-BIN-DCyn exhibits excellent aggregation-induced emission properties in both solution and solid states.
[0079] Example 7
[0080] The liquid crystal properties of R-BIN-DCyn prepared in Example 5 were tested:
[0081] To observe the liquid crystal behavior of R-BIN-DCyn, the sample was placed on a hot-stage slide of a polarizing optical microscope (POM) and covered with a coverslip. Gent pressure was applied to spread the sample evenly into a thin film. Within the liquid crystal phase temperature range, the phase transition behavior of the molecule was observed using the POM with an external heating stage, and the liquid crystal texture of the molecule was photographed. The magnification was 400x, and the heating and cooling rates of the hot stage were both 5°C / min. In phase transition studies, the cooling process is generally more conducive to monitoring birefringence. When the heating temperature exceeded 70°C, the sample began to melt, and the target molecule exhibited a phase transition behavior of crystallization-intermediate phase-isotropic state. Slow cooling from the isotropic state to the liquid crystal temperature range (around 140°C) was then performed. Figure 10 As shown, R-BIN-DCyn gradually exhibits birefringent liquid crystal textures, and a typical fan-shaped pseudo-focal cone texture can be clearly observed. This texture feature further confirms that R-BIN-DCyn possesses liquid crystal properties.
[0082] Example 8
[0083] The circular polarization luminescence properties of R-BIN-DCyn prepared in Example 5 were tested:
[0084] A dichloromethane solution of R-BIN-DCyn was uniformly dropped onto a quartz plate using a drop-coating method. The solvent was then evaporated at room temperature to obtain a solid film. The circularly polarized fluorescence spectrum of the solid film was measured at an excitation wavelength of 340 nm. Figure 11 ).from Figure 11 It can be seen that R-BIN-DCyn exhibits a significant CPL signal in the 450–600 nm range, consistent with the PL spectrum. R-BIN-DCyn also demonstrates a high chiral asymmetry factor in its solid-state thin film state. This invention, by introducing an R-binaphthyl unit into the molecular system, enables the transfer of chirality from the binaphthyl moiety to the dicyandiphenyl styrene (DCS) luminescent center, thereby endowing the entire molecule with chiral optical response.
[0085] In summary, R-BIN-DCyn exhibits excellent aggregation-induced emission properties, high solid-state fluorescence quantum yield, and circularly polarized luminescence performance in both solution and aggregated states. This result can be attributed to the fact that the DCS group itself has a distorted spatial configuration during aggregate formation. When it attaches to the R-binaphthyl framework, the molecules are stacked in a helical, ordered manner, further enhancing the circularly polarized luminescence performance of the system. Therefore, modifying the binaphthyl framework with a structurally distorted luminescent group can not only optimize the luminescence properties of the material but also significantly improve its asymmetry factor, providing an effective strategy for designing highly efficient circularly polarized luminescent materials.
[0086] The foregoing has shown and described the basic principles, main features, and advantages of the present invention. Those skilled in the art should understand that the present invention is not limited to the above embodiments. The embodiments and descriptions in the specification are merely illustrative of the principles of the invention. Various changes and modifications can be made to the invention without departing from its spirit and scope, and all such changes and modifications fall within the scope of the present invention as claimed. The scope of protection of this invention is defined by the appended claims and their equivalents.
Claims
1. A chiral binaphthol-cyanostilbene compound, abbreviated as R-BIN-DCyn, has the following structural formula: ； in, n=4~16。 2. The method for preparing the chiral binaphthol-cyanostilbene compound according to claim 1, characterized in that, The preparation method includes the following steps: (1) 4-hydroxyphenylacetonitrile reacts with terephthalaldehyde via a Knoevenagel condensation reaction to give intermediate 1; ； (2) R-6,6'-dihalo-1,1'-bi-2-naphthol undergoes a Suzuki coupling reaction with 4-ether phenylboronic acid to give intermediate 2; ； (3) Intermediate 2 undergoes a substitution reaction with 1-halododecane to give intermediate 3; ； (4) Intermediate 3 undergoes a substitution reaction with 1,4-dihalobutane to give intermediate 4; ； (5) Intermediate 1 and intermediate 4 undergo a substitution reaction to give R-BIN-DCyn; ； Where n = 4~16, and R is one of F, Cl, or Br.
3. The method for preparing chiral binaphthol-cyanostilbene compounds according to claim 2, characterized in that: The molar ratio of 4-hydroxyphenylacetonitrile to terephthalaldehyde is (2~4):1; Preferably, the Knoevenagel condensation reaction is carried out under the action of a base; Preferably, the base is selected from at least one of sodium hydroxide, pyridine, piperidine, and potassium tert-butoxide; Preferably, the reaction temperature of the Knoevenagel condensation reaction is 50~85℃.
4. The method for preparing chiral binaphthol-cyanostilbene compounds according to claim 2, characterized in that: The molar ratio of R-6,6'-dihalo-1,1'-bi-2-naphthol to 4-etherylphenylboronic acid is 1:(2.5~4.5); Preferably, the Suzuki coupling reaction is carried out in the presence of a base and a palladium catalyst; Preferably, the alkali is selected from at least one of potassium acetate, potassium carbonate, sodium acetate, sodium carbonate, and magnesium carbonate; Preferably, the reaction temperature of the Suzuki coupling reaction is 100~150℃.
5. The method for preparing chiral binaphthol-cyanostilbene compounds according to claim 2, characterized in that: The molar ratio of intermediate 2 to 1-halododecane is (1.2~1.8):
1.
6. The method for preparing chiral binaphthol-cyanostilbene compounds according to claim 2, characterized in that: The molar ratio of intermediate 3 to 1,4-dihalobutane is (1.5~3):
1.
7. The method for preparing chiral binaphthol-cyanostilbene compounds according to claim 2, characterized in that: The molar ratio of intermediate 1 to intermediate 4 is 1:(3~5).
8. The method for preparing chiral binaphthol-cyanostilbene compounds according to claim 2, characterized in that: The substitution reaction is carried out in the presence of an acid-binding agent selected from at least one of potassium carbonate, sodium sulfate, potassium iodide, potassium bromide, sodium iodide, sodium carbonate, sodium acetate, pyridine, and triethylamine. Preferably, the reaction temperature of the substitution reaction is 70~95℃.
9. The use of the chiral binaphthol-cyanostilbene compound of claim 1 as a chiral aggregation-induced emission liquid crystal material.
10. The application of the chiral aggregation-induced emission liquid crystal material according to claim 9 in organic light-emitting diodes and chiral fluorescent sensors.