Silathianone derivatives with green aggregation-induced emission characteristics and synthesis method and application thereof

Abstract

The application discloses a kind of silicon heteroanthracene derivatives with green aggregation-induced emission characteristics and synthesis method and application, belong to luminescent material technical field.The structural formula of the derivative is with silicon heteroanthracene as core, and 9,9-dimethylfluorene group is connected on both sides.The introduction of 9,9-dimethylfluorene forms twisted non-planar structure, so that the luminescence of molecule is significantly enhanced in aggregated state, AIE characteristics are obtained, while retaining the inherent σ* of silicon heteroanthracene-pi* conjugation effect and low LUMO energy level advantage.The synthesis method is based on suzuki coupling reaction, with 2,7-dichloro-9,9-dimethyl-9H-9-silicon heteroanthracene and 9,9-dimethylfluorene-2-boronic acid pinacol ester as raw material, under the action of catalyst, phosphine ligand and base in ethanol / water mixed solvent, mild condition, simple operation.The derivative can be used as efficient green light emitting material in electrochemiluminescence field, especially as electrochemiluminescence luminophor for detection of quercetin, with high detection sensitivity, good selectivity and strong anti-interference ability.

Description

Technical Field

[0001] This invention belongs to the field of luminescent materials technology, specifically relating to a siloxane derivative with green aggregation-induced emission properties, its synthesis method, and its application. Background Technology

[0002] Silicon xanthones, through the σ*-π* conjugation effect formed by the exocyclic σ* orbitals of silicon atoms and the π* orbitals of aromatic rings, exhibit excellent electronic structure characteristics. Effective orbital overlap enables efficient electron delocalization, significantly reducing the least occupied orbital (LUMO) energy level of the molecule while simultaneously enhancing electron affinity. Based on these outstanding advantages, silicon xanthones show broad application prospects in organic light-emitting materials, organic electron transport materials, and optoelectronic devices, becoming one of the research hotspots in the field of organic optoelectronics.

[0003] However, siloxane derivatives face the aggregation-caused quenching (ACQ) phenomenon due to their rigid structural framework. Because of the strong rigidity of their parent core and the highly planar molecular structure, siloxane derivatives are prone to π-π stacking, preventing the release of excited-state energy through radiative transitions. This results in weakened fluorescence intensity or even complete quenching, severely limiting their practical application in luminescent materials. The concept of aggregation-induced emission (AIE) successfully overcomes the ACQ phenomenon commonly found in traditional fluorescent molecules with rigid planar structures, providing a new approach for the design and application of luminescent materials. AIE refers to a photophysical phenomenon where molecules exhibit significantly enhanced luminescence in the aggregated or solid state compared to their solution state. Its core mechanism lies in the restricted intramolecular motion; in solution, intramolecular groups rotate freely, and excited-state energy dissipates non-radiatively, resulting in weak luminescence. When molecules exist in an aggregated state, the rotation of intramolecular groups is hindered, and excited-state energy is released through radiative transitions, thus achieving highly efficient photoluminescence.

[0004] Currently, methods to improve the ACQ phenomenon of siloxanthone derivatives are relatively limited. A common technique involves introducing sterically hindered groups such as tetraphenylethylene or triphenylamine to disrupt the π-π stacking between molecules through steric hindrance, thereby enabling the siloxanthone molecule to acquire AIE behavior. However, this method has certain drawbacks: the substitution reaction of sterically hindered groups like tetraphenylethylene and triphenylamine is difficult, and substitution failure is common in some scenarios, increasing the difficulty of material preparation. In contrast, 9,9-dimethylfluorene can be substituted under milder reaction conditions, making it easier to prepare the target product. Furthermore, its structural characteristics allow the substituted siloxanthone derivative to exhibit excellent AIE behavior and retain the inherent σ*-π* conjugation effect of the siloxanthone parent compound. Therefore, developing a preparation scheme with AIE behavior, mild synthesis conditions, and preservation of the inherent electronic structure advantages of the siloxanthone parent compound has become an urgent problem to be solved in the field of organic light-emitting materials.

[0005] Quercetin (Que), a typical representative of flavonoids, is a naturally occurring polyphenol widely found in nature, abundant in vegetables, fruits, and traditional Chinese medicines, and is one of the most important flavonoid antioxidants in nature. Its molecular structure contains multiple phenolic hydroxyl groups, endowing it with excellent free radical scavenging ability, thus exhibiting significant antioxidant activity. Studies have shown that Que possesses excellent antioxidant capacity, which is closely related to its ability to enhance cellular antioxidant capacity through mechanisms such as activating the Nrf2 / ARE signaling pathway. Furthermore, multiple experiments have shown that Que exhibits various potential pharmacological activities, including antiviral, anti-inflammatory, antitumor, and cardiovascular protective effects, demonstrating broad application prospects in natural medicines, functional foods, health products, and cosmetics. Therefore, constructing a sensitive and stable Que sensor to achieve rapid detection of Que in biological samples is of great significance for promoting the research and practical application of quercetin. Summary of the Invention

[0006] The purpose of this invention is to overcome the shortcomings of existing technologies and provide a siloxane derivative with green AIE properties. This derivative, by introducing a 9,9-dimethylfluorene group, successfully transforms ACQ properties into AIE properties while maintaining the low LUMO energy level advantage brought by the σ*-π* conjugation effect of the siloxane parent compound.

[0007] Another object of the present invention is to provide a method for synthesizing the above-mentioned siloxane derivatives. This method is based on the Suzuki coupling reaction, is mild, simple to operate, low in cost, and yields good results.

[0008] Another object of the present invention is to provide the above-mentioned siloxane derivatives as organic light-emitting materials, particularly for use in organic electroluminescent devices.

[0009] A fourth objective of this invention is to provide the application of the above-mentioned siloxane derivatives in electrochemiluminescence (ECL) detection, particularly for constructing an ECL sensing system for detecting quercetin (Que).

[0010] To achieve the above objectives, the present invention adopts the following technical solution: A siloxane derivative exhibiting green aggregation-induced emission properties has the following structural formula: .

[0011] This molecule has a siloxane core with 9,9-dimethylfluorene groups covalently bonded to both sides. The introduction of the 9,9-dimethylfluorene groups disrupts the original planarity of the siloxane, forming a distorted three-dimensional structure and a non-planar π-conjugated system. In solution, this structure allows free rotation of intramolecular groups, consuming excited-state energy and resulting in weak luminescence; however, in the aggregated state, intramolecular rotation is restricted, and excited-state energy is mainly released through radiative transitions, thus exhibiting significant AIE (Active Electron Emission) characteristics. Simultaneously, the inherent σ*-π* conjugation effect of the siloxane core is preserved, ensuring that the molecule still possesses a low LUMO energy level and good electron transport capabilities.

[0012] The method for synthesizing the above-mentioned siloxane derivatives with green aggregation-induced emission properties includes the following steps: 2,7-Dichloro-9,9-dimethyl-9H-9-silicanthrone, 9,9-dimethylfluorene-2-boronate pinacol ester, palladium acetate catalyst, phosphine ligand 2-di-tert-butylphospho-2',4',6'-triisopropylbiphenyl, and potassium basic phosphate were dissolved in a mixed solvent of ethanol and water. The reaction system was purged with an inert gas (e.g., nitrogen) to remove oxygen, and then stirred at 90°C–100°C (preferably 95°C) for 20–28 hours (preferably 24 hours) to complete the Suzuki coupling reaction. After the reaction, the reaction mixture was extracted with an organic solvent (e.g., dichloromethane), and the organic phase was collected and concentrated under reduced pressure to remove the solvent, yielding the crude product. The crude product was purified by silica gel column chromatography using a mixed solvent of dichloromethane and petroleum ether (volume ratio 3:1–5:1, preferably 4:1) as the eluent, finally yielding the target silicanthrone derivative.

[0013] Preferably, the proportions of each reactant are as follows: The molar ratio of 2,7-dichloro-9,9-dimethyl-9H-9-siloxane to 9,9-dimethylfluorene-2-boronic acid pinacol ester is 1:2 to 1:3, preferably 1:2.5. For the synthesis of 2,7-dichloro-9,9-dimethyl-9H-9-siloxane, refer to Delcamp, Jared Heath; Nghombui, David Ndaleh Dodah; Meador, William Edward. “Silicone-based dyes and methods for making and using the same.” US Patent WO2022 / 241405 A1, issued 17 November 2022.

[0014] The molar amount of palladium acetate catalyst is 10% to 30% of the molar amount of 2,7-dichloro-9,9-dimethyl-9H-9-siloxane, preferably 20%.

[0015] The molar amount of the phosphine ligand 2-di-tert-butylphospho-2',4',6'-triisopropylbiphenyl is 20% to 50% of the molar amount of 2,7-dichloro-9,9-dimethyl-9H-9-siloxane, preferably 40%.

[0016] The molar amount of potassium phosphate is 1.5 to 3 times that of 2,7-dichloro-9,9-dimethyl-9H-9-siloxane, preferably 2 times.

[0017] The volume ratio of ethanol to water in the mixed solvent is 3:1 to 5:1, preferably 4:1.

[0018] This invention provides the application of the above-mentioned siloxane-anthraquinone derivative as an organic light-emitting material. This invention also provides the application of the above-mentioned siloxane-anthraquinone derivative in the fabrication of organic electroluminescent devices (such as OLEDs). This derivative can be used as a light-emitting layer material or an electron transport layer material.

[0019] This invention provides the application of the above-mentioned siloxane derivatives in electrochemiluminescence detection. The siloxane derivatives are used as electrochemiluminescent emitters to construct an electrochemiluminescence sensing system.

[0020] The electrochemiluminescence sensing system comprises the siloxane derivative and a co-reactant. The co-reactant is preferably a persulfate, such as K₂S₂O₈.

[0021] The electrochemiluminescence sensing system described above is used to detect quercetin. The luminescence signal of this derivative in the ECL system composed of K₂S₂O₈ can be effectively quenched by quercetin, and the degree of quenching is linearly related to the quercetin concentration within a certain range, thus enabling quantitative detection of quercetin.

[0022] Quantitative detection of quercetin was achieved by measuring the linear relationship between quercetin concentration and electrochemiluminescence signal intensity. The linear equation corresponding to the linear relationship is I = -13.6 [Que] + 11423.5, where I is the electrochemiluminescence signal intensity and [Que] is the quercetin concentration. The linear range for quercetin detection is 20–500 μM. This method exhibits high sensitivity and selectivity and can be used for the detection of quercetin in complex samples (such as human serum).

[0023] This invention utilizes a Suzuki coupling reaction to modify the structure of a siloxane derivative by introducing 9,9-dimethylfluorene groups on both sides. On one hand, it retains the inherent σ*-π* conjugation effect of the siloxane derivative, resulting in a low least unoccupied orbital (LUMO) energy level and excellent electron affinity, ensuring good electron transport capabilities. On the other hand, it overcomes the aggregation-induced quenching (ACQ) property of the siloxane derivative, endowing it with AIE (Alternating Electron Emission) properties and significantly improving the luminescence efficiency. This invention aims to solve the technical problem of the ACQ phenomenon in existing siloxane derivatives, which hinders their practical application. Furthermore, the preparation process is based on Suzuki coupling, with mild reaction conditions and low cost. The resulting derivative can be applied to organic light-emitting materials, possessing significant practical application value.

[0024] Compared with the prior art, the present invention has the following beneficial effects: 1. Successful Attribution of AIE Properties: This invention cleverly disrupts the planarity of the molecule by introducing a bulky, rigid 9,9-dimethylfluorene group at the 2,7 positions of the siloxane, forming a twisted three-dimensional structure. In solution, intramolecular rotation leads to nonradiative transitions, resulting in weak luminescence; however, in the aggregated state, intramolecular motion is restricted (RIM), opening radiative transition channels and thus exhibiting a significant AIE effect, effectively overcoming the ACQ problem of traditional siloxanes.

[0025] 2. Retaining excellent electronic properties: The modified derivatives still retain the inherent σ*-π* conjugation effect of the siloxane core, have a low LUMO energy level and good electron affinity / transport ability, which lays the foundation for its application in the optoelectronic field.

[0026] 3. Simple and efficient synthesis method: This invention employs a one-step Suzuki coupling reaction to synthesize the target molecule from commercially available or easily prepared raw materials. The reaction conditions are mild (water / alcohol mixed solvent, moderate temperature), the catalyst system is highly efficient, the post-processing is simple, and the yield is good, making it suitable for large-scale preparation.

[0027] 4. Excellent luminescence performance: The obtained derivatives emit bright green fluorescence in the aggregated state and have a large Stokes shift, which helps to reduce self-absorption and improve luminescence efficiency.

[0028] 5. Excellent quercetin detection performance: The ECL system based on this derivative exhibits a sensitive response to quercetin. The ECL signal is linearly quenched with increasing quercetin concentration, showing a wide linear range and good linearity. It also demonstrates high selectivity for common interfering substances (such as urea, glucose, and amino acids). This ECL sensing system showed high accuracy and reliability in human serum spiked recovery experiments, indicating its potential for detecting quercetin in complex real-world samples and its significant practical application prospects.

[0029] 6. Broad application prospects: This AIE-active siloxane derivative can be used as a high-performance green light-emitting material in fields such as OLED, chemical / biological sensors, and photodetectors, and has important practical application value. Attached Figure Description

[0030] Figure 1 The luminescent siloxane derivative synthesized in Example 1 of this invention 1 H-NMR spectrum.

[0031] Figure 2 The siloxane derivative synthesized in Example 1 of this invention 13 C-NMR spectrum.

[0032] Figure 3 This is a high-resolution mass spectrum of the siloxane derivative synthesized in Example 1 of the present invention.

[0033] Figure 4 This is a single-crystal XRD diffraction structure of the siloxane derivative synthesized in Example 1 of the present invention.

[0034] Figure 5 The UV-Vis absorption spectrum of the siloxane derivative synthesized in Example 1 of this invention is shown.

[0035] Figure 6 The fluorescence emission spectrum of the siloxane derivative synthesized in Example 1 of this invention in its aggregated state in N,N-dimethylformamide as a good solvent and ethanol as a poor solvent is shown.

[0036] Figure 7The fluorescence excitation and emission spectra of the siloxane derivative synthesized in Example 1 of this invention are shown.

[0037] Figure 8 The fluorescence emission spectra of the aggregated states of the siloxane derivative synthesized in Example 1 of this invention in different unsuitable solvents are shown.

[0038] Figure 9 The electrochemiluminescence stability test diagram of the siloxane derivative synthesized in Example 1 of the present invention in the presence of K2S2O8 co-reactant (25 consecutive scans).

[0039] Figure 10 The diagram shows the quenching effect of different concentrations of quercetin on the electrochemiluminescence signal of the siloxane derivative system of this invention.

[0040] Figure 11 This is a graph showing the linear relationship between the concentration of quercetin and the electrochemiluminescence signal intensity of the siloxane derivative system of the present invention.

[0041] Figure 12 This is a graph showing the anti-interference effect of the siloxane derivative system of the present invention on the detection of quercetin. Detailed Implementation

[0042] The present invention will be further described in detail below with reference to the accompanying drawings and embodiments. The following embodiments are used to illustrate the present invention, but are not intended to limit the scope of the present invention.

[0043] Example 1: Synthesis of siloxane derivatives The reaction formula for siloxane derivatives is as follows: 2,7-Dichloro-9,9-dimethyl-9H-9-siloxane (0.75 mmol, 0.2295 g), 9,9-dimethylfluorene-2-boronate pinacol ester (1.875 mmol, 0.8595 g), palladium acetate (20 mol%, 0.0336 g), 2-di-tert-butylphosphino-2',4',6'-triisopropylbiphenyl (40 mol%, 0.1273 g), and potassium phosphate (1.5 mmol, 0.3184 g) were dissolved in ethanol (20 mL) and double-distilled water (5 mL). A mixed solution (mL) was prepared, and the system was purged with nitrogen. The mixture was stirred in an oil bath at 95°C for 24 hours to induce a Suzuki coupling reaction. After the reaction, the mixture was extracted with dichloromethane to separate the layers. The organic phase was collected and evaporated under reduced pressure. Using dichloromethane and petroleum ether at a volume ratio of 4:1 as eluent, the mixture was purified by silica gel column chromatography to obtain 0.1179 g of a green solid product with a yield of 25.25%, which is a siloxane derivative.

[0044] The obtained product was structurally characterized, such as Figure 1 ,2 Characterization data of the obtained siloxane derivatives: 3, 4, 1 The H NMR spectral data are as follows: 1 H NMR (400 MHz, Chloroform-d) δ (ppm) 8.61 (d,J =8.3 Hz, 2H), 7.98 (d, J = 1.8 Hz, 2H), 7.91 (dd, J = 8.3, 1.9 Hz, 2H), 7.86(d, J = 7.9 Hz, 2H), 1.60 (s, 12H), 0.67 (s, 6H). 13 The C NMR spectral data are as follows: 13 C NMR (600 MHz, Chloroform-d) δ (ppm)187.34,154.48, 153.99, 144.69, 139.70, 139.67, 139.49, 139.26, 138.58, 131.75,130.34, 128.99, 127.62, 127.13, 126.57, 122.69, 121.59, 120.48, 120.27,47.06, 27.24,-1.17. High-resolution mass spectrometry data are: HRMS m / z Calculated for C 45 H 38 OSi [H] + 623.2765, found 623.2764. The 1H NMR, 1C NMR, and high-resolution mass spectrometry data all matched the structure of the target molecule, confirming the successful synthesis of the target product. Example 2 Single Crystal Structure Determination The product obtained in Example 1 was cultured into single crystals using a solvent diffusion method (dichloromethane / methanol). The single crystals were analyzed using an X-ray single-crystal diffractometer. Crystallographic data are shown in Table 1, and the molecular structure is as follows: Figure 4As shown in the diagram, the crystal structure clearly reveals a significant twist angle between the two 9,9-dimethylfluorene groups and the central siloxane plane, forming a non-planar spatial configuration. This structurally explains the molecule's AIE properties.

[0045] Example 3: Photophysical property testing 1. UV-Vis absorption spectroscopy: The product obtained in Example 1 was dissolved in tetrahydrofuran to prepare a solution of 10... -3 The solution of M was tested using a UV-Vis spectrophotometer. The results are as follows: Figure 5 As shown, characteristic absorption peaks appear at 218 nm, 276 nm and 352 nm.

[0046] 2. Aggregation-induced emission (AIE) property test: First, the product was dissolved in N,N-dimethylformamide (DMF) to prepare a solution of 1×10⁻⁶. -3 A stock solution of M was prepared. Then, a series of mixed solutions of DMF and ethanol (a poor solvent) were prepared, with ethanol volume fractions (fv%) of 0%, 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80%, 90%, 95%, and 98%. An equal volume (20 μL) of the above stock solution was added to each mixed solvent system to ensure a consistent final test concentration. The fluorescence emission spectra of each mixed system were measured using a fluorescence spectrometer (excitation wavelength 365 nm). The results are as follows: Figure 6 As shown, the fluorescence intensity is very weak in pure DMF (fv%=0); as the proportion of the poor solvent ethanol increases, the molecules begin to aggregate and the fluorescence intensity gradually increases. The fluorescence intensity reaches its maximum when the fv% reaches 90%, exhibiting typical AIE characteristics.

[0047] 3. Fluorescence spectroscopy: Tests the fluorescence excitation and emission spectra of the product, such as... Figure 7 As shown, its maximum emission wavelength is approximately 514 nm, which falls within the green light region, and its Stokes shift is approximately 122 nm.

[0048] 4. Fluorescence in different unsuitable solvents: The fluorescence emission spectra of the product in different unsuitable solvents (methanol, ethanol, n-propanol, n-butanol, n-pentanol) were tested, such as... Figure 8 As shown, in different undesirable solvents, its maximum emission wavelength exhibits a significant red shift with increasing solvent polarity. This indicates that the DAD-type structure formed by the dimethylfluorene flanking the siloxane as the acceptor in the DMFMHBS molecule has a significant intramolecular charge transfer (ICT) effect.

[0049] Example 4: Electrochemiluminescence performance testing and application 1. ECL Stability Test: The siloxane derivative (denoted as DMFMHBS) obtained in Example 1 was dissolved in DMF to prepare a 1 mmol / L stock solution. ECL testing was performed using a three-electrode system: a glassy carbon electrode (GCE) as the working electrode (polished with 0.3 μm and 0.05 μm Al₂O₃ powders before use), a platinum electrode as the counter electrode, and an Ag / AgCl electrode as the reference electrode. 20 μL of the above DMFMHBS stock solution was added to a phosphate buffer solution (PBS, pH=7.4) containing 0.1 M K₂S₂O₈. Detection was performed using an MPI-A / B capillary electrophoresis-electrochemiluminescence analyzer. Test conditions: photomultiplier tube high voltage 800 V, scan potential range -1.8 V ~ 0 V, scan rate 0.16 V / s. Results are as follows: Figure 9 As shown, the ECL system stabilized its signal after 25 consecutive scans, with a relative standard deviation (RSD) of only 0.47%, indicating that it has excellent stability and is suitable for building sensors.

[0050] 2. Quercetin assay: A series of 0.1 MK2S2O8 PBS (pH=7.4) solutions containing different concentrations of quercetin (Que, concentration range 0-500 μM) were prepared. 20 μL of 1 mmol / L DMFMHBS stock solution was added to each solution for ECL testing. Results are as follows: Figure 10 As shown, the ECL signal intensity gradually decreases with increasing quercetin concentration, indicating that quercetin has a quenching effect on the ECL system.

[0051] 3. Linearity and Sensitivity: Data on quercetin concentrations ranging from 20 μM to 500 μM were linearly fitted to the corresponding ECL signal intensities. The results are as follows: Figure 11 As shown, there is a good linear relationship between quercetin concentration ([Que]) and ECL signal intensity (I), with the linear equation being I = -13.6 [Que] + 11423.5 and a correlation coefficient R. 2 = 0.9957. This indicates that the system can be used for the quantitative detection of quercetin.

[0052] 4. Selectivity Test: To evaluate the selectivity of the sensing system, potentially interfering substances, including urea, glucose (Glc), threonine (Thr), cysteine ​​(Cys), alanine (Ala), and arginine (Arg), were added to a PBS system containing DMFMHBS and K2S2O8. The results are as follows: Figure 12As shown, these interfering substances have no significant effect on the ECL signal intensity, indicating that the system has high selectivity for quercetin.

[0053] 5. Spiked Recovery Experiment of Real Samples: To verify the applicability of this ECL sensing system to complex real-world samples, a spiked recovery experiment was conducted on human serum samples. Different concentrations of quercetin standards (25 μM, 45 μM, 65 μM) were added to human serum samples, and then the ECL method described above was used for detection. The results are shown in Table 2. The recoveries of the detected amounts ranged from 98.2% to 100.9%, and the relative standard deviations (RSDs) were all less than 4%, demonstrating the accuracy and reliability of this method in the analysis of real samples.

[0054] The above description is merely a preferred embodiment of the present invention and is not intended to limit the invention. Various modifications and variations can be made to the present invention by those skilled in the art. Any modifications, equivalent substitutions, improvements, etc., made within the spirit and principles of the present invention should be included within the scope of protection of the present invention.

Claims

1. A siloxane derivative with green aggregation-induced emission properties, characterized in that, The structural formula of the siloxane derivative is: 。 2. The siloxane derivative according to claim 1, characterized in that, The siloxane derivative consists of a siloxane host and 9,9-dimethylfluorene groups on both sides, forming a distorted three-dimensional structure and a non-planar π-conjugated system.

3. A method for synthesizing a siloxane derivative with green aggregation-induced luminescence according to claim 1 or 2, characterized in that, Includes the following steps: 2,7-Dichloro-9,9-dimethyl-9H-9-siloxane, 9,9-dimethylfluorene-2-boronic acid pinacol ester, catalyst, phosphine ligand and base were dissolved in a mixed solvent of ethanol and water, and Suzuki coupling reaction was carried out under an inert atmosphere. After the reaction was completed, the siloxane derivative was obtained by extraction, concentration and column chromatography purification.

4. The synthesis method according to claim 3, characterized in that, The molar ratio of 2,7-dichloro-9,9-dimethyl-9H-9-siloxane to 9,9-dimethylfluorene-2-boronate pinacol ester is 1:2 to 1:3; the catalyst is palladium acetate, and its molar amount is 10% to 30% of the molar amount of 2,7-dichloro-9,9-dimethyl-9H-9-siloxane; the phosphine ligand is 2-di-tert-butylphosphino-2',4',6'-triisopropylbiphenyl, and its molar amount is 2... The solvent is 20% to 50% of the molar amount of 2,7-dichloro-9,9-dimethyl-9H-9-siloxane; the base is potassium phosphate, and its molar amount is 1.5 to 3 times the molar amount of 2,7-dichloro-9,9-dimethyl-9H-9-siloxane; the volume ratio of ethanol to water in the mixed solvent is 3:1 to 5:1; the reaction temperature of the Suzuki coupling reaction is 90℃ to 100℃, and the reaction time is 20 to 28 hours.

5. The application of a siloxane derivative according to claim 1 or 2 as an organic light-emitting material.

6. The application of a siloxane derivative according to claim 1 or 2 in electrochemiluminescence detection.

7. The application according to claim 6, characterized in that, The siloxane derivatives were used as electrochemiluminescent emitters to construct an electrochemiluminescent sensing system.

8. The application according to claim 7, characterized in that, The electrochemiluminescence sensing system comprises the siloxane derivative and the co-reactant persulfate.

9. The application according to claim 7 or 8, characterized in that, The electrochemiluminescence sensing system is used to detect quercetin.

10. In the application according to claim 9, there is a linear relationship between the concentration of quercetin and the intensity of the electrochemiluminescence signal, the linear range for detecting quercetin is 20~500 μM, and the linear equation is I = -13.6 [Que] + 11423.5, R 2 =0.9957, where I is the electrochemiluminescence signal intensity and [Que] is the quercetin concentration.

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