Alkoxy silane with fluorescence characteristic and preparation method thereof

Abstract

The invention relates to the technical field of organic silicon monomer synthesis, in particular to alkoxy silane with fluorescence characteristics and a preparation method thereof. The alkoxy silane is prepared by carrying out addition reaction on activated alkyne containing an electron withdrawing group and an alkoxy silane monomer containing a primary amino group, an alkoxy silane monomer containing a secondary amino group and an alkoxy silane monomer simultaneously containing the primary amino group and the secondary amino group at-20 DEG C to room temperature, and has a fluorescence characteristic; wherein the molar ratio of alkynyl in the activated alkyne containing the electron withdrawing group to primary amino groups, secondary amino groups or the sum of the primary amino groups and the secondary amino groups in the three alkoxy silane monomers is x: 1, and x is the number of the primary amino groups, the secondary amino groups or the sum of the primary amino groups and the secondary amino groups in each alkoxy silane monomer. The preparation method provided by the invention does not need heating, does not need to add a catalyst and an organic solvent, and has the advantages of simple synthesis steps, convenient post-treatment and high yield.

Description

Technical Field

[0001] This invention relates to the field of organosilicon monomer synthesis technology, specifically to an alkoxysilane with fluorescent properties and its preparation method. Background Technology

[0002] Alkoxysilanes are a class of organosilicon compounds containing two functional groups with different chemical properties, with the general formula Y-Si-X3. X is a hydrolyzable organic functional group (such as methoxy or ethoxy), and Y is a non-hydrolyzable functional group that can react with organic matter (such as amino, mercapto, or vinyl groups). The silanol groups produced after the X group hydrolyzes readily combine with inorganic materials (such as glass and metals), while the Y group has a good binding ability with organic materials such as resins and rubber. Therefore, alkoxysilanes can connect two different materials at the interface and improve the performance of composite materials. They are widely used in surface modifiers, adhesives, sealants, coating tackifiers, and filled plastics, and are indispensable key additives in modern industry.

[0003] The preparation of alkoxysilanes usually requires organic solvents and catalysts, and a long heating reaction to obtain the product. The product contains many byproducts, which need to be purified by various post-processing methods to finally obtain the alkoxysilane monomer. The process is complicated, time-consuming, and has high requirements for equipment and operation. The most common synthesis methods are as follows: (1) Direct synthesis method: Silica powder and haloalkanes are reacted directly at high temperature (~300℃) under the action of copper catalyst to generate a mixture of methylchlorosilanes. The target product is then obtained through separation, alcoholysis and other steps. Although this method is mature and low in cost, it has defects such as poor reaction selectivity, harsh reaction conditions (high temperature and high pressure), and difficulty in separation and purification. It is only suitable for synthesizing simple alkoxysilanes such as methyl and ethyl, and it is difficult to introduce more complex functional groups, thus limiting its application range. (2) Grignard reagent method: This method is commonly used in the laboratory. First, haloalkanes with the target functional group are made into Grignard reagents, and then they are condensed with silicon tetrachloride. Finally, the target product is obtained by hydrolysis. The advantage of this method is that it can introduce a wide variety of organic functional groups and the product has high purity. However, its disadvantages are that the entire synthetic route has many steps, the Grignard reagent is extremely sensitive to water, the production conditions are harsh, a large amount of waste liquid is contained in the reaction process, the post-treatment is complicated, and the cost is high, making it difficult to carry out large-scale production. (3) Hydrosilylation method: This is an important method for producing alkoxysilanes containing alkenyl, epoxy and other groups. It uses intermediates containing silane-hydrogen bonds and olefins with unsaturated bonds to react under the catalysis of noble metals such as platinum. This method has a short procedure, good selectivity, and is suitable for continuous scale-up production. However, its problem is that it depends on expensive and easily poisoned and deactivated platinum catalysts, and there are side reactions in the reaction. It also has extremely high requirements for the purity of raw materials and process control.

[0004] In summary, existing methods for synthesizing alkoxysilanes have shortcomings in terms of reaction selectivity, product purity, cost control, reaction conditions, and environmental protection. Furthermore, with the continuous expansion of the application scope of alkoxysilanes, existing methods are unable to meet the new demands for the structure and properties of alkoxysilanes. Therefore, we propose a green synthesis method for alkoxysilanes that solves the above problems. Summary of the Invention

[0005] To address the shortcomings of existing technologies, the present invention aims to provide a fluorescent alkoxysilane and its preparation method. This synthetic method can obtain fluorescent alkoxysilanes through an addition reaction between an amino-containing alkoxysilane monomer and an activated alkyne containing an electron-withdrawing group, without the need for a catalyst and under conditions of low temperature or room temperature. The reaction rate is fast, the post-processing is convenient, and the yield is high.

[0006] The present invention provides a method for preparing fluorescent alkoxysilanes. The method involves reacting activated alkynes containing electron-withdrawing groups with alkoxysilane monomers containing primary amino groups, alkoxysilane monomers containing secondary amino groups, and alkoxysilane monomers containing both primary and secondary amino groups at a temperature of -20°C to room temperature to synthesize fluorescent alkoxysilanes. In activated alkynes containing electron-withdrawing groups, the molar ratio of the alkyne group to the primary amino group, secondary amino group, or the sum of both in the three alkoxysilane monomers is x:1, where x is the number of primary amino groups, secondary amino groups, or the sum of both in each alkoxysilane monomer.

[0007] Preferably, the activated alkyne containing an electron-withdrawing group includes, but is not limited to, methyl propargylate, dimethyl butargyl diacidate, ethyl 4,4,4-trifluorobutargylate, 3-butyn-2-one, 1-phenyl-2-propyn-1-one, 4-trimethylsilyl-3-butyn-2-one, or alkynyl-p-tolyl sulfone.

[0008] The structural formula of an activated alkyne containing an electron-withdrawing group is R1-C≡C-R2, wherein at least one of R1 and R2 is an electron-withdrawing group; When R1 is H and R2 is -COOCH3, the activated alkyne containing the electron-withdrawing group is methyl propynate; when both R1 and R2 are -COOCH3, the activated alkyne is dimethyl butynedioate; when R1 is -CF3 and R2 is -COOCH2CH3, the activated alkyne is ethyl 4,4,4-trifluorobutynedioate; when R1 is H and R2 is -COCH3, the activated alkyne is 3-butyn-2-one; when R1 is H and R2 is -CO-C6H5, the activated alkyne is 1-phenyl-2-propyn-1-one; when R1 is -Si(CH3)3 and R2 is -COCH3, the activated alkyne is 4-trimethylsilyl-3-butyn-2-one; when R1 is H and R2 is -SO2-C6H4-CH3, the activated alkyne is alkynyl-p-tolyl sulfone.

[0009] Preferably, the alkoxysilane monomer containing a primary amino group includes aminopropyltrimethoxysilane, aminopropyltriethoxysilane, aminopropylmethyldimethoxysilane, aminopropylmethyldiethoxysilane, and aminopropyldimethylmethoxysilane; Alkoxysilane monomers containing secondary amino groups include bis(3-trimethoxysilylpropyl)amine; Alkoxysilane monomers that contain both primary and secondary amino groups include [3-(6-aminohexylamino)propyl]trimethoxysilane or 3-[2-(2-aminoethylamino)ethylamino]propyl-trimethoxysilane.

[0010] The amino-containing alkoxysilane monomer has the structural formula (R3)(R4)(R5)Si-(R6), where R 3, R 4, In R5, one to three groups are -COOCH3 or -COOCH2CH3, and the rest are -CH3. R6 contains one or more amino groups (at least one primary or secondary amine group). 3, R 4, When R5 is -COOCH3 and R6 is -(CH2)3NH2, the aminoalkoxysilane monomer is aminopropyltrimethoxysilane; when R 3, R 4, When R5 is -COOCH2CH3 and R6 is -(CH2)3NH2, the aminoalkoxysilane monomer is aminopropyltriethoxysilane; when R3 is -CH3, R 4, When R5 is -COOCH3 and R6 is -(CH2)3NH2, the aminoalkoxysilane monomer is aminopropylmethyldimethoxysilane; when R3 is -CH3, R 4,When R5 is -COOCH2CH3 and R6 is -(CH2)3NH2, the aminoalkoxysilane monomer is aminopropylmethyldiethoxysilane; when R3 and R5 are -CH3, R4 is -COOCH3, and R6 is -(CH2)3NH2, the aminoalkoxysilane monomer is aminopropyldimethylmethoxysilane; when R3 and R5 are -CH3, R4 is -COOCH2CH3, and R6 is -(CH2)3NH2, the aminoalkoxysilane monomer is aminopropyldimethylethoxysilane; when R... 3, R 4, When R5 is -COOCH3 and R6 is -(CH2)3NH(CH2)3Si(OCH3)3, the aminoalkoxysilane monomer is di(3-trimethoxysilylpropyl)amine; when R 3, R 4, When R5 is -COOCH3 and R6 is -(NH2)3NH(NH2)6NH2, the aminoalkoxysilane monomer is [3-(6-aminohexylamino)propyl]trimethoxysilane; when R 3, R 4, When R5 is -COOCH3 and R6 is -(CH2)3NH(CH2)2NH(CH2)2NH2, the aminoalkoxysilane monomer is 3-[2-(2-aminoethylamino)ethylamino]propyl-trimethoxysilane.

[0011] Preferably, the molar ratio of methyl propargylate, dimethyl butynedioate, ethyl 4,4,4-trifluorobutargylate, 3-butyn-2-one, 1-phenyl-2-propyn-1-one, 4-trimethylsilyl-3-butyn-2-one or alkynyl-p-tolyl sulfone to aminopropyltriethoxysilane is 1:1; or, The molar ratio of methyl propargylate, dimethyl butynedioate, ethyl 4,4,4-trifluorobutargylate, 3-butyn-2-one, 1-phenyl-2-propyn-1-one, 4-trimethylsilyl-3-butyn-2-one or alkynyl-p-tolyl sulfone to aminopropyltrimethoxysilane is 1:1; or, The molar ratio of methyl propargylate, dimethyl butynedioate, ethyl 4,4,4-trifluorobutargylate, 3-butyn-2-one, 1-phenyl-2-propyn-1-one, 4-trimethylsilyl-3-butyn-2-one or alkynyl-p-tolyl sulfone to aminopropylmethyldiethoxysilane is 1:1; or, The molar ratio of methyl propargylate, dimethyl butynedioate, ethyl 4,4,4-trifluorobutargylate, 3-butyn-2-one, 1-phenyl-2-propyn-1-one, 4-trimethylsilyl-3-butyn-2-one or alkynyl-p-tolyl sulfone to aminopropylmethyldiethoxysilane is 1:1; or, The molar ratio of methyl propargylate, dimethyl butynedioate, ethyl 4,4,4-trifluorobutargylate, 3-butyn-2-one, 1-phenyl-2-propyn-1-one, 4-trimethylsilyl-3-butyn-2-one or alkynyl-p-tolyl sulfone to aminopropyl diethylmethoxysilane is 1:1; or, The molar ratio of methyl propargylate, dimethyl butynedioate, ethyl 4,4,4-trifluorobutargylate, 3-butyn-2-one, 1-phenyl-2-propyn-1-one, 4-trimethylsilyl-3-butyn-2-one or alkynyl-p-tolyl sulfone to aminopropyl dimethylmethoxysilane is 1:1; or, The molar ratio of methyl propargylate, dimethyl butynedioate, ethyl 4,4,4-trifluorobutargylate, 3-butyn-2-one, 1-phenyl-2-propyn-1-one, 4-trimethylsilyl-3-butyn-2-one or alkynyl-p-tolyl sulfone to di(3-trimethoxysilylpropyl)amine is 1:1; or, The molar ratio of methyl propynate, dimethyl butynedioate, ethyl 4,4,4-trifluorobutynedioate, 3-butyn-2-one, 1-phenyl-2-propyn-1-one, 4-trimethylsilyl-3-butyn-2-one or alkynyl-p-tolyl sulfone to [3-(6-aminohexylamino)propyl]trimethoxysilane is 2:1; or, The molar ratio of methyl propynate, dimethyl butynedioate, ethyl 4,4,4-trifluorobutynedioate, 3-butyn-2-one, 1-phenyl-2-propyn-1-one, 4-trimethylsilyl-3-butyn-2-one or alkynyl-p-tolyl sulfone to 3-[2-(2-aminoethylamino)ethylamino]propyl-trimethoxysilane is 3:1.

[0012] Preferably, the alkoxysilane monomer containing a primary amino group, the alkoxysilane monomer containing a secondary amino group, or the alkoxysilane monomer containing both primary and secondary amino groups are added dropwise to the activated alkyne containing an electron-withdrawing group at a dropping rate of 0.1 ml / min to 1.0 ml / min.

[0013] Preferably, the addition reaction time is 3 min to 1 h.

[0014] The present invention also provides a method for preparing fluorescent alkoxysilanes.

[0015] Compared with the prior art, the beneficial effects of the present invention are as follows: This invention involves the addition reaction of activated alkynes containing electron-withdrawing groups with alkoxysilane monomers containing primary amino groups, secondary amino groups, and both primary and secondary amino groups. This reaction is highly reactive, and the reaction process is monitored using infrared absorption spectroscopy. It was observed that the reaction is complete within 3 minutes to 1 hour after the reactants are added, indicating a very rapid reaction. No organic solvents or catalysts are required during the reaction, and heating is unnecessary. The reaction can be carried out at temperatures ranging from -20°C to above room temperature to obtain alkoxysilanes. The unpurified alkoxysilanes were analyzed using 1H NMR spectroscopy, revealing the absence of byproducts. The reaction is green, and alkoxysilanes can be obtained without complex post-treatment methods, with a high yield.

[0016] Furthermore, the alkoxysilane prepared by this invention contains multiple functional groups such as double bonds, amino groups, carbonyl groups, ester groups, and sulfone groups, and has a conjugated structure of double bonds and carbonyl groups. It exhibits fluorescence properties as measured by a fluorescence spectrophotometer. Its fluorescence originates from clustering and intramolecular interactions, making it a novel luminescent material. Its luminescence principle differs from that of traditional fluorescent materials, belonging to non-traditional fluorescence. It exhibits an aggregation-induced emission effect, with a stronger luminescence effect at higher concentrations in solution. In contrast, traditional fluorescent materials typically exhibit an aggregation-induced quenching effect, with their fluorescence efficiency decreasing sharply at high concentrations. Due to its unique properties, non-traditional fluorescent materials may find applications and development in polymer and biomedical fields in the future. Attached Figure Description

[0017] Figure 1 This is an infrared image of the product prepared in Example 1 of the present invention. Figure 2 This is the 1H NMR spectrum of aminopropyltriethoxysilane, methyl propynate, and the product prepared in Example 1 of this invention.

[0018] Figure 3 The fluorescence spectrum is obtained by mixing the product prepared in Example 1 of this invention with dichloromethane to form a 1.0 mol / L mixture.

[0019] Figure 4 The fluorescence spectra are obtained by mixing the product prepared in Example 1 of the present invention with dichloromethane to form mixed solutions of different concentrations. Detailed Implementation

[0020] To make the above-mentioned objectives, features, and advantages of the embodiments of the present invention more apparent and understandable, the technical solutions of the embodiments of the present invention will be clearly and completely described below with reference to the accompanying drawings. Obviously, the described embodiments are merely some embodiments of the present invention, and not all embodiments. All other embodiments obtained by those skilled in the art without creative effort are within the scope of protection of the present invention.

[0021] It should be noted that when numerical ranges are involved in this invention, it should be understood that the two endpoints of each numerical range and any value between the two endpoints can be selected. Since the steps and methods used are the same as those in Embodiments 1 to 25, preferred embodiments are described in this invention to avoid redundancy. However, this invention is not limited to these, but can be specifically implemented in other ways within the scope of the technical solutions defined in the appended claims.

[0022] The technical solution of the present invention will be further illustrated below with specific examples.

[0023] In the following embodiments, unless otherwise specified, the methods described are conventional methods, and the reagents described are commercially available unless otherwise specified.

[0024] Alkoxysilane monomers containing primary amino groups, alkoxysilane monomers containing secondary amino groups, or alkoxysilane monomers containing both primary and secondary amino groups were added dropwise to activated alkynes containing electron-withdrawing groups at a dropping rate of 0.1 ml / min to 1.0 ml / min to prepare fluorescent alkoxysilane monomers. The following experiments were conducted using a dropping rate of 0.25 ml / min.

[0025] In addition, alkoxysilane monomers containing primary amino groups, including aminopropyltrimethoxysilane, aminopropyltriethoxysilane, aminopropylmethyldimethoxysilane, aminopropylmethyldiethoxysilane, and aminopropyldimethylmethoxysilane, can all undergo addition reactions with activated alkynes containing electron-withdrawing groups. In the following examples, aminopropyltrimethoxysilane is used as an example of an alkoxysilane monomer containing primary amino groups.

[0026] Alkoxysilane monomers containing both primary and secondary amino groups, including [3-(6-aminohexylamino)propyl]trimethoxysilane or 3-[2-(2-aminoethylamino)ethylamino]propyl-trimethoxysilane, can undergo addition reactions with activated alkynes containing electron-withdrawing groups. [3-(6-aminohexylamino)propyl]trimethoxysilane is used as an example in the following embodiments as an alkoxysilane monomer containing both primary and secondary amino groups.

[0027] Example 1 A method for preparing an alkoxysilane with fluorescent properties includes the following steps: Take 0.84 g (10 mmol) of methyl propargylate into a 25 mL two-necked flask, add a rotor, and then place the flask in a low-temperature reaction chamber. Set the temperature of the low-temperature reaction chamber to 5 °C and turn on the magnetic stirrer. Connect one end of the two-necked flask to the discharge tube of a peristaltic pump, and insert a thermocouple thermometer into the other end. Then, take 2.21 g (10 mmol) of aminopropyltriethoxysilane into a 10 mL test tube, insert the feed tube of the peristaltic pump into the test tube, and set the feed rate of the peristaltic pump to 0.25 m / s. At a rate of L / min, the peristaltic pump was turned on, and aminopropyltriethoxysilane was gradually added dropwise into a two-necked flask. During the addition, the liquid in the flask gradually changed from colorless to pale yellow, releasing a large amount of heat. The thermocouple thermometer reading continuously increased. After all the aminopropyltriethoxysilane was titrated, the temperature gradually stabilized. After cooling to room temperature, a sample was taken for infrared spectroscopy. After the infrared monitoring showed that the reaction was complete, the product was taken out and weighed, with a yield of 97% and a reaction time of 10 min. Its structure and configuration were finally determined by proton nuclear magnetic resonance spectroscopy.

[0028] Example 2 A method for preparing an alkoxysilane with fluorescent properties includes the following steps: 1.42 g (10 mmol) of dimethyl butyrynethate was placed in a 25 mL two-necked flask, a rotor was added, and the flask was placed in a low-temperature reaction vessel. The temperature of the reaction vessel was set to 5 °C, and the magnetic stirrer was turned on. One end of the flask was connected to the discharge tube of a peristaltic pump, and the other end was inserted into a thermocouple. Then, 2.21 g (10 mmol) of aminopropyltriethoxysilane was placed in a 10 mL test tube, and the feed tube of the peristaltic pump was inserted into the test tube. The feed rate of the peristaltic pump was set to 0.25 rpm. At a rate of mL / min, the peristaltic pump was turned on, and aminopropyltriethoxysilane was gradually added dropwise into a two-necked flask. During the addition, the liquid in the flask gradually changed from colorless to brown, releasing a large amount of heat. The thermocouple thermometer reading continuously increased. After all the aminopropyltriethoxysilane was titrated, the temperature gradually stabilized. After cooling to room temperature, a sample was taken for infrared spectroscopy. After the infrared monitoring showed that the reaction was complete, the product was taken out and weighed, with a yield of 96% and a reaction time of 10 min. Its structure and configuration were finally determined by proton nuclear magnetic resonance spectroscopy.

[0029] Example 3 A method for preparing an alkoxysilane with fluorescent properties includes the following steps: Take 1.66 g (10 mmol) of ethyl 4,4,4-trifluorobutynedate into a 25 mL two-necked flask, add a rotor, and then place the two-necked flask in a low-temperature reaction chamber. Set the temperature of the low-temperature reaction chamber to 5 °C and turn on the magnetic stirrer. Connect one end of the two-necked flask to the discharge tube of a peristaltic pump and insert a thermocouple thermometer into the other end. Then take 2.21 g (10 mmol) of aminopropyltriethoxysilane into a 10 mL test tube, insert the feed tube of the peristaltic pump into the test tube, and set the feed rate of the peristaltic pump to 0. At a rate of 25 mL / min, the peristaltic pump was turned on, and aminopropyltriethoxysilane was gradually added dropwise into a two-necked flask. During the addition, the liquid in the flask gradually changed from colorless to orange-red, releasing a large amount of heat. The thermocouple thermometer reading continuously increased. After all the aminopropyltriethoxysilane had been titrated, the temperature gradually stabilized. After cooling to room temperature, a sample was taken for infrared spectroscopy. After the infrared monitoring showed that the reaction was complete, the product was taken out and weighed, with a yield of 97%. The reaction time was 10 min. Its structure and configuration were finally determined by proton nuclear magnetic resonance spectroscopy.

[0030] Example 4 A method for preparing an alkoxysilane with fluorescent properties includes the following steps: Take 0.68 g (10 mmol) of 3-butyn-2-one into a 25 mL two-necked flask, add a rotor, and then place the flask in a low-temperature reaction chamber. Set the temperature of the low-temperature reaction chamber to 5 °C and turn on the magnetic stirrer. Connect one end of the two-necked flask to the discharge tube of a peristaltic pump, and insert a thermocouple thermometer into the other end. Then, take 2.21 g (10 mmol) of aminopropyltriethoxysilane into a 10 mL test tube, insert the feed tube of the peristaltic pump into the test tube, and set the feed rate of the peristaltic pump to 0.25. At a rate of mL / min, the peristaltic pump was turned on, and aminopropyltriethoxysilane was gradually added dropwise into a two-necked flask. During the addition, the liquid in the flask gradually changed from colorless to pale yellow, releasing a large amount of heat. The thermocouple thermometer reading continuously rose. After all the aminopropyltriethoxysilane was titrated, the temperature gradually stabilized. After cooling to room temperature, a sample was taken for infrared spectroscopy. After the infrared monitoring showed that the reaction was complete, the product was taken out and weighed, with a yield of 98% and a reaction time of 10 min. Its structure and configuration were finally determined by proton nuclear magnetic resonance spectroscopy.

[0031] Example 5 A method for preparing an alkoxysilane with fluorescent properties includes the following steps: Take 1.30 g (10 mmol) of 1-phenyl-2-propyn-1-one into a 25 mL two-necked flask, add a rotor, and then place the two-necked flask in a low-temperature reaction chamber. Set the temperature of the low-temperature reaction chamber to 5 °C and turn on the magnetic stirrer. Connect one end of the two-necked flask to the discharge tube of a peristaltic pump and insert a thermocouple thermometer into the other end. Then, take 2.21 g (10 mmol) of aminopropyltriethoxysilane into a 10 mL test tube, insert the feed tube of the peristaltic pump into the test tube, and set the feed rate of the peristaltic pump to 0. At a rate of 0.25 mL / min, a peristaltic pump was turned on, and aminopropyltriethoxysilane was gradually added dropwise into a two-necked flask. During the addition, the liquid in the flask gradually changed from colorless to deep yellow, releasing a large amount of heat. The thermocouple thermometer reading continuously increased. After all the aminopropyltriethoxysilane had been titrated, the temperature gradually stabilized. After cooling to room temperature, a sample was taken for infrared spectroscopy. After the infrared spectroscopy confirmed the reaction was complete, the product was weighed, yielding 98%, with a reaction time of 10 min. Its structure and configuration were ultimately determined by proton nuclear magnetic resonance spectroscopy.

[0032] Example 6 A method for preparing an alkoxysilane with fluorescent properties includes the following steps: Take 1.40 g (10 mmol) of 4-trimethylsilyl-3-butyn-2-one into a 25 mL two-necked flask, add a rotor, and then place the flask in a low-temperature reaction chamber. Set the temperature of the low-temperature reaction chamber to 5 °C and turn on the magnetic stirrer. Connect one end of the two-necked flask to the discharge tube of a peristaltic pump and insert a thermocouple thermometer into the other end. Then, take 2.21 g (10 mmol) of aminopropyltriethoxysilane into a 10 mL test tube, insert the feed tube of the peristaltic pump into the test tube, and set the feed rate of the peristaltic pump to [value missing]. At a rate of 0.25 mL / min, a peristaltic pump was turned on, and aminopropyltriethoxysilane was gradually added dropwise into a two-necked flask. During the addition, the liquid in the flask gradually changed from colorless to orange, releasing a large amount of heat. The thermocouple thermometer reading continuously increased. After all the aminopropyltriethoxysilane had been titrated, the temperature gradually stabilized. After cooling to room temperature, a sample was taken for infrared spectroscopy. After the infrared spectroscopy confirmed the reaction was complete, the product was weighed, yielding 99%, with a reaction time of 10 min. Its structure and configuration were ultimately determined by proton nuclear magnetic resonance spectroscopy.

[0033] Example 7 A method for preparing an alkoxysilane with fluorescent properties includes the following steps: Take 1.80 g (10 mmol) of alkynyl-p-tolyl sulfone into a 25 mL two-necked flask, add a rotor, and then place the flask in a low-temperature reaction chamber. Set the temperature of the low-temperature reaction chamber to 5 °C and turn on the magnetic stirrer. Connect one end of the two-necked flask to the discharge tube of a peristaltic pump, and insert a thermocouple thermometer into the other end. Then, take 2.21 g (10 mmol) of aminopropyltriethoxysilane into a 10 mL test tube, insert the feed tube of the peristaltic pump into the test tube, and set the feed rate of the peristaltic pump to 0.25. At a rate of mL / min, the peristaltic pump was turned on, and aminopropyltriethoxysilane was gradually added dropwise into a two-necked flask. During the addition, the liquid in the flask gradually changed from colorless to orange-red, releasing a large amount of heat. The thermocouple thermometer reading continuously increased. After all the aminopropyltriethoxysilane was titrated, the temperature gradually stabilized. After cooling to room temperature, a sample was taken for infrared spectroscopy. After the infrared monitoring showed that the reaction was complete, the product was taken out and weighed, with a yield of 98% and a reaction time of 10 min. Its structure and configuration were finally determined by proton nuclear magnetic resonance spectroscopy.

[0034] Example 8 A method for preparing an alkoxysilane with fluorescent properties includes the following steps: Take 0.84 g (10 mmol) of methyl propargylate into a 25 mL two-necked flask, add a rotor, and then place the flask in a low-temperature reaction chamber. Set the temperature of the low-temperature reaction chamber to 5 °C and turn on the magnetic stirrer. Connect one end of the two-necked flask to the discharge tube of a peristaltic pump and insert a thermocouple thermometer into the other end. Then, take 3.41 g (10 mmol) of di(3-trimethoxysilylpropyl)amine into a 10 mL test tube, insert the feed tube of the peristaltic pump into the test tube, and set the feed rate of the peristaltic pump to 0.25 mL / m. In a two-necked flask, the peristaltic pump was turned on, and bis(3-trimethoxysilylpropyl)amine was gradually added dropwise through the pump. During the addition, the liquid in the flask gradually changed from colorless to yellow, releasing a large amount of heat, and the thermocouple thermometer reading continuously increased. After all the bis(3-trimethoxysilylpropyl)amine had been titrated, the temperature gradually stabilized. After cooling to room temperature, a sample was taken for infrared spectroscopy. After the infrared monitoring showed that the reaction was complete, the product was taken out and weighed, with a yield of 98% and a reaction time of 10 minutes. Its structure and configuration were finally determined by proton nuclear magnetic resonance spectroscopy.

[0035] Example 9 A method for preparing an alkoxysilane with fluorescent properties includes the following steps: 1.42 g (10 mmol) of dimethyl butyrynethide was placed in a 25 mL two-necked flask, a rotor was added, and the flask was placed in a low-temperature reaction chamber. The temperature of the low-temperature reaction chamber was set to 5 °C, and the magnetic stirrer was turned on. One end of the two-necked flask was connected to the discharge tube of a peristaltic pump, and the other end was inserted into a thermocouple thermometer. Then, 3.41 g (10 mmol) of di(3-trimethoxysilylpropyl)amine was placed in a 10 mL test tube, and the feed tube of the peristaltic pump was inserted into the test tube. The feed rate of the peristaltic pump was set to 0.25 mL / m. In a two-necked flask, the peristaltic pump was turned on, and bis(3-trimethoxysilylpropyl)amine was gradually added dropwise through the pump. During the addition, the liquid in the flask gradually changed from colorless to brownish-red, releasing a large amount of heat. The thermocouple thermometer reading continuously increased. After all the bis(3-trimethoxysilylpropyl)amine had been titrated, the temperature gradually stabilized. After cooling to room temperature, a sample was taken for infrared spectroscopy. After the infrared monitoring showed that the reaction was complete, the product was taken out and weighed, with a yield of 97% and a reaction time of 10 minutes. Its structure and configuration were finally determined by proton nuclear magnetic resonance spectroscopy.

[0036] Example 10 A method for preparing an alkoxysilane with fluorescent properties includes the following steps: Take 1.66 g (10 mmol) of ethyl 4,4,4-trifluorobutynedate into a 25 mL two-necked flask, add a rotor, and then place the flask in a low-temperature reaction vessel. Set the temperature of the low-temperature reaction vessel to 5 °C and turn on the magnetic stirrer. Connect one end of the two-necked flask to the discharge tube of a peristaltic pump and insert a thermocouple thermometer into the other end. Then, take 3.41 g (10 mmol) of di(3-trimethoxysilylpropyl)amine into a 10 mL test tube, insert the feed tube of the peristaltic pump into the test tube, and set the feed rate of the peristaltic pump to 0.25 mL. At a rate of 1 min, the peristaltic pump was turned on, and di(3-trimethoxysilylpropyl)amine was gradually added dropwise into a two-necked flask. During the addition, the liquid in the flask gradually changed from colorless to orange-red, releasing a large amount of heat. The thermocouple thermometer reading continuously increased. After all the di(3-trimethoxysilylpropyl)amine had been titrated, the temperature gradually stabilized. After cooling to room temperature, a sample was taken for infrared spectroscopy. After the infrared monitoring showed that the reaction was complete, the product was taken out and weighed, with a yield of 96.5% and a reaction time of 10 min. Its structure and configuration were finally determined by proton nuclear magnetic resonance spectroscopy.

[0037] Example 11 A method for preparing an alkoxysilane with fluorescent properties includes the following steps: Take 0.68 g (10 mmol) of 3-butyn-2-one into a 25 mL two-necked flask, add a rotor, and then place the flask in a low-temperature reaction chamber. Set the temperature of the low-temperature reaction chamber to 5 °C and turn on the magnetic stirrer. Connect one end of the two-necked flask to the discharge tube of a peristaltic pump and insert a thermocouple thermometer into the other end. Then, take 3.41 g (10 mmol) of di(3-trimethoxysilylpropyl)amine into a 10 mL test tube, insert the feed tube of the peristaltic pump into the test tube, and set the feed rate of the peristaltic pump to 0.25 mL / min. For 10 minutes, the peristaltic pump was turned on, and di(3-trimethoxysilylpropyl)amine was gradually added dropwise into a two-necked flask. During the addition, the liquid in the flask gradually changed from colorless to deep yellow, releasing a large amount of heat. The thermocouple thermometer reading continuously increased. After all the di(3-trimethoxysilylpropyl)amine had been titrated, the temperature gradually stabilized. After cooling to room temperature, a sample was taken for infrared spectroscopy. After the infrared monitoring showed that the reaction was complete, the product was taken out and weighed, with a yield of 99%. The reaction time was 10 minutes. Its structure and configuration were finally determined by proton nuclear magnetic resonance spectroscopy.

[0038] Example 12 A method for preparing an alkoxysilane with fluorescent properties includes the following steps: Take 1.30 g (10 mmol) of 1-phenyl-2-propyn-1-one into a 25 mL two-necked flask, add a rotor, and then place the flask in a low-temperature reaction chamber. Set the temperature of the low-temperature reaction chamber to 5 °C and turn on the magnetic stirrer. Connect one end of the two-necked flask to the discharge tube of a peristaltic pump and insert a thermocouple thermometer into the other end. Then, take 3.41 g (10 mmol) of di(3-trimethoxysilylpropyl)amine into a 10 mL test tube, insert the feed tube of the peristaltic pump into the test tube, and set the feed rate of the peristaltic pump to 0.25 m / s. At a rate of L / min, the peristaltic pump was turned on, and di(3-trimethoxysilylpropyl)amine was gradually added dropwise into a two-necked flask. During the addition, the liquid in the flask gradually changed from colorless to brownish-red, releasing a large amount of heat. The thermocouple thermometer reading continuously increased. After all the di(3-trimethoxysilylpropyl)amine had been titrated, the temperature gradually stabilized. After cooling to room temperature, a sample was taken for infrared spectroscopy. After the infrared monitoring showed that the reaction was complete, the product was taken out and weighed, with a yield of 98% and a reaction time of 10 min. Its structure and configuration were finally determined by proton nuclear magnetic resonance spectroscopy.

[0039] Example 13 A method for preparing an alkoxysilane with fluorescent properties includes the following steps: Take 1.40 g (10 mmol) of 4-trimethylsilyl-3-butyn-2-one into a 25 mL two-necked flask, add a rotor, and then place the flask in a low-temperature reaction chamber. Set the temperature of the low-temperature reaction chamber to 5 °C and turn on the magnetic stirrer. Connect one end of the two-necked flask to the discharge tube of a peristaltic pump and insert a thermocouple thermometer into the other end. Then, take 3.41 g (10 mmol) of di(3-trimethoxysilylpropyl)amine into a 10 mL test tube, insert the feed tube of the peristaltic pump into the test tube, and set the feed rate of the peristaltic pump to 0.25. The peristaltic pump was turned on at a rate of mL / min, and bis(3-trimethoxysilylpropyl)amine was gradually added dropwise into a two-necked flask. During the addition, the liquid in the flask gradually changed from colorless to deep yellow, releasing a large amount of heat. The thermocouple thermometer reading continuously increased. After all the bis(3-trimethoxysilylpropyl)amine had been titrated, the temperature gradually stabilized. After cooling to room temperature, a sample was taken for infrared spectroscopy. After the infrared monitoring showed that the reaction was complete, the product was taken out and weighed, with a yield of 98% and a reaction time of 10 min. Its structure and configuration were finally determined by proton nuclear magnetic resonance spectroscopy.

[0040] Example 14 A method for preparing an alkoxysilane with fluorescent properties includes the following steps: Take 1.80 g (10 mmol) of alkynyl-p-tolyl sulfone into a 25 mL two-necked flask, add a rotor, and then place the flask in a low-temperature reaction chamber. Set the temperature of the low-temperature reaction chamber to 5 °C and turn on the magnetic stirrer. Connect one end of the two-necked flask to the discharge tube of a peristaltic pump and insert a thermocouple thermometer into the other end. Then, take 3.41 g (10 mmol) of di(3-trimethoxysilylpropyl)amine into a 10 mL test tube, insert the feed tube of the peristaltic pump into the test tube, and set the feed rate of the peristaltic pump to 0.25 mL / m. In a two-necked flask, the peristaltic pump was turned on, and bis(3-trimethoxysilylpropyl)amine was gradually added dropwise through the pump. During the addition, the liquid in the flask gradually changed from colorless to deep orange, releasing a large amount of heat. The thermocouple thermometer reading continuously increased. After all the bis(3-trimethoxysilylpropyl)amine had been titrated, the temperature gradually stabilized. After cooling to room temperature, a sample was taken for infrared spectroscopy. After the infrared monitoring showed that the reaction was complete, the product was taken out and weighed, with a yield of 97% and a reaction time of 10 minutes. Its structure and configuration were finally determined by proton nuclear magnetic resonance spectroscopy.

[0041] Example 15 The only difference between Example 15 and Example 1 is that the temperature of the low-temperature reaction tank is -20°C, and the product is taken out and weighed after the reaction is completed by infrared monitoring, with a yield of 94%.

[0042] Example 16 The only difference between Example 16 and Example 1 is that a low-temperature reaction tank was not used; the reaction was carried out at room temperature. After the reaction was completed, the product was taken out and weighed, and the yield was 92%.

[0043] Example 17 The difference between Example 17 and Example 1 is that aminopropyltriethoxysilane was replaced with [3-(6-aminohexylamino)propyl]trimethoxysilane, and the weight of [3-(6-aminohexylamino)propyl]trimethoxysilane was 1.39 g (5 mmol). After the reaction was completed as monitored by infrared spectroscopy, the product was weighed, and the yield was 99%. The reaction time was 15 min. Its structure and configuration were ultimately determined by 1H NMR spectroscopy.

[0044] Example 18 The difference between Example 18 and Example 2 is that aminopropyltriethoxysilane was replaced with [3-(6-aminohexylamino)propyl]trimethoxysilane, and the weight of [3-(6-aminohexylamino)propyl]trimethoxysilane was 1.39 g (5 mmol). After the reaction was completed as monitored by infrared spectroscopy, the product was weighed, and the yield was 98%. The reaction time was 15 min. Its structure and configuration were ultimately determined by 1H NMR spectroscopy.

[0045] Example 19 The difference between Example 19 and Example 3 is that aminopropyltriethoxysilane was replaced with [3-(6-aminohexylamino)propyl]trimethoxysilane, and the weight of [3-(6-aminohexylamino)propyl]trimethoxysilane was 1.39 g (5 mmol). After the reaction was completed as monitored by infrared spectroscopy, the product was weighed, and the yield was 99%. The reaction time was 15 min. Its structure and configuration were ultimately determined by 1H NMR spectroscopy.

[0046] Example 20 The difference between Example 20 and Example 4 is that aminopropyltriethoxysilane was replaced with [3-(6-aminohexylamino)propyl]trimethoxysilane, and the weight of [3-(6-aminohexylamino)propyl]trimethoxysilane was 1.39 g (5 mmol). After the reaction was completed as monitored by infrared spectroscopy, the product was weighed, and the yield was 98.5%, with a reaction time of 15 min. Its structure and configuration were ultimately determined by 1H NMR spectroscopy.

[0047] Example 21 The difference between Example 21 and Example 5 is that aminopropyltriethoxysilane was replaced with [3-(6-aminohexylamino)propyl]trimethoxysilane, and the weight of [3-(6-aminohexylamino)propyl]trimethoxysilane was 1.39 g (5 mmol). After the reaction was completed as monitored by infrared spectroscopy, the product was weighed, and the yield was 99%. The reaction time was 15 min. Its structure and configuration were ultimately determined by 1H NMR spectroscopy.

[0048] Example 22 The difference between Example 22 and Example 6 is that aminopropyltriethoxysilane was replaced with [3-(6-aminohexylamino)propyl]trimethoxysilane, and the weight of [3-(6-aminohexylamino)propyl]trimethoxysilane was 1.39 g (5 mmol). After the reaction was completed as monitored by infrared spectroscopy, the product was weighed, and the yield was 98%. The reaction time was 15 min. Its structure and configuration were ultimately determined by 1H NMR spectroscopy.

[0049] Example 23 The difference between Example 23 and Example 6 is that aminopropyltriethoxysilane was replaced with [3-(6-aminohexylamino)propyl]trimethoxysilane, and the weight of [3-(6-aminohexylamino)propyl]trimethoxysilane was 1.39 g (5 mmol). After the reaction was completed as monitored by infrared spectroscopy, the product was weighed, and the yield was 97%. The reaction time was 15 min. Its structure and configuration were ultimately determined by 1H NMR spectroscopy.

[0050] Example 24 The only difference between Example 24 and Example 1 is that the reaction time is 3 minutes, the product is taken out and weighed, and the yield is 95%.

[0051] Example 25 The only difference between Example 25 and Example 1 is that the reaction time is 1 hour and the yield of the product is 99% when weighed.

[0052] Fluorescent alkoxysilanes were prepared in all of the above Examples 1 to 25. The following is an experimental test of the fluorescent alkoxysilane prepared in Example 1.

[0053] Experimental verification (1) Infrared testing like Figure 1 As shown, the carbon-carbon triple bond vibration peak at 2124 in the infrared spectrum of methyl propargylate disappeared in the infrared spectrum of the product, and a new carbon-carbon double bond vibration peak at 1611 was added in the product. At the same time, the carbonyl vibration peak originally located at 1725 in the infrared spectrum of methyl propargylate was red-shifted to 1692 due to the influence of the carbon-carbon double bond ester group conjugated structure in the product, proving that the desired alkoxysilane was generated.

[0054] (2) Proton NMR spectroscopy analysis like Figure 2 As shown, in the 1H NMR spectrum of the raw material, the hydrogen atom in the carbon-carbon triple bond of methyl propargylate at a chemical shift of 2.92 ppm disappears in the product, indicating that the addition reaction was complete. Meanwhile, in the product's NMR spectrum, the peaks at chemical shifts of 3.03 ppm–3.18 ppm correspond to hydrogen atoms on the methylene group attached to ammonia after the amino-alkynyl group reaction; the peaks at chemical shifts of 3.64–3.66 ppm correspond to hydrogen atoms on the methyl group attached to the ester bond; and the peaks at chemical shifts of 4.44–4.46 ppm, 6.61–6.66 ppm, and 4.71–4.74 ppm, 7.47–7.52 ppm correspond to hydrogen atoms on the carbon-carbon double bond formed after the reaction, respectively. These correspond to the E and Z configurations of the product, with a ratio of 70 / 30. The 1H NMR data clearly demonstrates that the reaction produced an alkoxysilane with the predicted structure, and also verifies the accuracy of the infrared detection results.

[0055] (3) Fluorescence spectrophotometry: A 1.0 mol / L mixed solution was prepared by dissolving the fluorescent alkoxysilane obtained in Example 1 in dichloromethane.

[0056] Depend on Figure 3 As can be seen from the detection, the product exhibits fluorescent properties, while the reactants methyl propynate and aminopropyltriethoxysilane show no fluorescent signal. This indicates that the fluorescence originates from the alkoxysilane monomer formed by the reaction of the two, with a maximum excitation wavelength of 437 nm and a maximum emission wavelength of 497 nm. However, its structure does not contain traditional fluorescent groups such as large π bonds and aromatic rings. Its fluorescence may originate from the clusters of secondary / tertiary amines, silicon-oxygen bonds, carbon-carbon double bonds, and ester groups in the product structure. Therefore, this product belongs to a non-traditional fluorescent organosilicon compound.

[0057] To further verify that the product prepared in the examples has non-traditional fluorescent properties, the product prepared in Example 1 was dissolved in dichloromethane to prepare 0.1 mol / L mixed solutions, 0.5 mol / L mixed solutions, and 1.0 mol / L mixed solutions.

[0058] Depend on Figure 4It can be seen that as the concentration of the mixed solution increases, the fluorescence intensity gradually increases, the shape of the emission spectrum changes, and the position of the emission wavelength also shows a certain degree of red shift, exhibiting the aggregation-induced enhancement effect and fluorescence red shift characteristics of non-traditional fluorescent compounds. The reason is that at low concentrations, non-traditional chromophores are dispersed in the solution, forming fewer clusters. As the concentration increases, it promotes the transformation of non-traditional chromophores from a discrete state to an aggregated state, promoting the formation of a large number of clusters, thereby enhancing the fluorescence intensity and red shifting the emission wavelength, further proving that the synthesized product has non-traditional fluorescent properties.

[0059] Obviously, those skilled in the art can make various modifications and variations to this invention without departing from its spirit and scope. Therefore, if these modifications and variations fall within the scope of the claims of this invention and their equivalents, this invention also intends to include these modifications and variations.

Claims

1. A method for producing an alkoxysilane having a fluorescent property, characterized by, The method is that the activated alkyne containing electron-withdrawing group respectively reacts with the alkoxysilane monomer containing primary amino group, the alkoxysilane monomer containing secondary amino group and the alkoxysilane monomer containing both primary amino group and secondary amino group at-20℃ to room temperature to synthesize the alkoxysilane with fluorescence; The molar ratio of the alkynyl in the activated alkyne containing electron-withdrawing group to the sum of the primary amino group, the secondary amino group or both in the three alkoxysilane monomers is x:1, and x is the number of the sum of the primary amino group, the secondary amino group or both in each alkoxysilane monomer.

2. The method for preparing alkoxysilanes with fluorescent properties according to claim 1, characterized in that, The activated alkyne containing electron-withdrawing group includes methyl propiolate, dimethyl butyne diacid, ethyl 4,4,4-trifluorobutyne acid, 3-butyne-2-ketone, 1-phenyl-2-propyne-1-ketone or 4-trimethylsilyl-3-butyne-2-ketone or alkynyl p-tolyl sulfone.

3. The method for preparing alkoxysilanes with fluorescent properties according to claim 2, characterized in that, The alkoxysilane monomer containing primary amino group includes aminopropyl trimethoxysilane, aminopropyl triethoxysilane, aminopropyl methyl dimethoxysilane, aminopropyl methyl diethoxysilane, aminopropyl dimethyl methoxysilane and aminopropyl dimethyl ethoxysilane. The alkoxysilane monomer containing secondary amino group includes di(3-trimethoxysilylpropyl) amine. The alkoxysilane monomer containing both primary amino group and secondary amino group includes [3-(6-aminohexylamino) propyl] trimethoxysilane or 3-[2-(2-aminoethylamino) ethylamino] propyl-trimethoxysilane.

4. The method for preparing alkoxysilanes with fluorescent properties according to claim 3, characterized in that, The molar ratio of methyl propiolate, dimethyl butyne diacid, ethyl 4,4,4-trifluorobutyne acid, 3-butyne-2-ketone, 1-phenyl-2-propyne-1-ketone, 4-trimethylsilyl-3-butyne-2-ketone or alkynyl p-tolyl sulfone to aminopropyl triethoxysilane is 1:1; or, The molar ratio of methyl propiolate, dimethyl butyne diacid, ethyl 4,4,4-trifluorobutyne acid, 3-butyne-2-ketone, 1-phenyl-2-propyne-1-ketone, 4-trimethylsilyl-3-butyne-2-ketone or alkynyl p-tolyl sulfone to aminopropyl triethoxysilane is 1:1; or, The molar ratio of methyl propiolate, dimethyl butyne diacid, ethyl 4,4,4-trifluorobutyne acid, 3-butyne-2-ketone, 1-phenyl-2-propyne-1-ketone, 4-trimethylsilyl-3-butyne-2-ketone or alkynyl p-tolyl sulfone to aminopropyl triethoxysilane is 1:1; or, The molar ratio of methyl propiolate, dimethyl butyne diacid, ethyl 4,4,4-trifluorobutyne acid, 3-butyne-2-ketone, 1-phenyl-2-propyne-1-ketone, 4-trimethylsilyl-3-butyne-2-ketone or alkynyl p-tolyl sulfone to aminopropyl triethoxysilane is 1:1; or, The molar ratio of methyl propiolate, dimethyl butyne diacid, ethyl 4,4,4-trifluorobutyne acid, 3-butyne-2-ketone, 1-phenyl-2-propyne-1-ketone, 4-trimethylsilyl-3-butyne-2-ketone or alkynyl p-tolyl sulfone to aminopropyl triethoxysilane is 1:1; or, The molar ratio of methyl propiolate, dimethyl butyne diacid, ethyl 4,4,4-trifluorobutyne acid, 3-butyne-2-ketone, 1-phenyl-2-propyne-1-ketone, 4-trimethylsilyl-3-butyne-2-ketone or alkynyl p-tolyl sulfone to aminopropyl triethoxysilane is 1:1; or, The molar ratio of the methyl propiolate, dimethyl butyne diacid, ethyl 4,4,4 trifluorobutyne acid, 3-butyne-2-ketone, 1-phenyl-2-propyne-1-ketone, 4-trimethylsilyl-3-butyne-2-ketone or alkynyl p-tolyl sulfone to the amino propyl dimethyl methoxysilane is 1:1; or, The molar ratio of the methyl propiolate, dimethyl butyne diacid, ethyl 4,4,4 trifluorobutyne acid, 3-butyne-2-ketone, 1-phenyl-2-propyne-1-ketone, 4-trimethylsilyl-3-butyne-2-ketone or alkynyl p-tolyl sulfone to the di(3-trimethoxysilylpropyl) amine is 1:1; or, The molar ratio of the methyl propiolate, dimethyl butyne diacid, ethyl 4,4,4 trifluorobutyne acid, 3-butyne-2-ketone, 1-phenyl-2-propyne-1-ketone, 4-trimethylsilyl-3-butyne-2-ketone or alkynyl p-tolyl sulfone to the [3-(6-aminohexylamino)propyl] trimethoxysilane is 2:1; or, The molar ratio of the methyl propiolate, dimethyl butyne diacid, ethyl 4,4,4 trifluorobutyne acid, 3-butyne-2-ketone, 1-phenyl-2-propyne-1-ketone, 4-trimethylsilyl-3-butyne-2-ketone or alkynyl p-tolyl sulfone to the 3-[2-(2-aminoethylamino)ethylamino]propyl-trimethoxysilane is 3:

1.

5. The method for preparing alkoxysilanes with fluorescent properties according to claim 1, characterized in that, The primary amino group-containing alkoxysilane monomer, the secondary amino group-containing alkoxysilane monomer or the alkoxysilane monomer containing both primary and secondary amino groups is added dropwise into the electron-withdrawing group-containing activated alkyne at a dropwise adding speed of 0.1 ml / min to 1.0 ml / min.

6. The method for preparing alkoxysilanes with fluorescent properties according to claim 1, characterized in that, The addition reaction lasts for 3 min to 1 h.

7. The alkoxysilane with fluorescence prepared by the method of any one of claims 1 to 6 has fluorescence.

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