One-step preparation method of fluorescent single-chain polymer nanoparticles

Abstract

The invention discloses a one-step preparation method of fluorescent single-chain polymer nanoparticles, and particularly relates to the field of high polymer chemistry. Comprising the following steps: dissolving polyethylene glycol methyl ether methacrylate, a cyanostilbene methacrylate monomer and an initiator in a ninth solvent to obtain a reaction solution, and carrying out polymerization reaction on the reaction solution in a nitrogen environment to obtain poly ((Z)-2-(2-(2-(4-(2-cyano-2-(3, 4, 5-trimethylphenyl) phenyl)-1, 3, 5-trimethylphenyl)-1, 3, 5-trimethylphenyl)-1, 3, 5-trimethylphenyl)-1, 3, 5- 2, 5-tri (dodecyloxy) phenyl) vinyl) hydroxyl ethyoxyl) ethyoxyl) ethyoxyl) ethyoxyl) ethyl methacrylate-polyethylene glycol methyl ether methacrylate); and dissolving the product in water to obtain a copolymer solution, irradiating the copolymer solution under an ultraviolet lamp, and carrying out freeze-drying separation to obtain the fluorescent single-chain polymer nanoparticles. And the one-step preparation of the fluorescent polymer single-chain nanoparticles is realized.

Description

Technical Field

[0001] The present application relates to the field of preparation methods of fluorescent single-chain polymers, and in particular to a "one-step" preparation method of fluorescent single-chain polymer nanoparticles. Background Art

[0002] Single-chain polymer nanoparticles are small-sized materials (less than 20 nm) prepared by cross-linking within polymer chains. Their formation process can mimic the folding and molecular transport functions of proteins, and therefore have become a research hotspot in the fields of chemistry, materials science, and life sciences. Among them, single-chain polymer nanoparticles with fluorescent properties have recently attracted widespread research enthusiasm due to their excellent biocompatibility and fluorescent function, and have been applied in the fields of catalysis, biosensors, nanoreactors, nanomedicines, etc.

[0003] Document 1 "JF Hoffmann, AH Roos, F.-J. Schmitt, D. Hinderberger, and W. H. Binder. Fluorescent and Water Dispersible Single-Chain Nanoparticles: Core-Shell Structured Compartmentation. Angew. Chem. Int. Ed. 2021, 60, 7820-7827" discloses a single-chain polymer nanoparticle that first uses a click reaction between an azide and an alkyne group as an intrachain folding mechanism, and then labels the formed single-chain polymer nanoparticles with a fluorescent dye to obtain fluorescent single-chain polymer nanoparticles. This method for preparing fluorescent single-chain polymer nanoparticles requires more than two chemical reaction steps, and the formed single-chain polymer nanoparticles require additional reactive functional groups to introduce fluorescent moieties, and the introduction of fluorescent moieties has many structural uncertainties, making it difficult to achieve a simple one-step preparation.

[0004] Reference 2 “Y. Shao, Y.-L. Wang, Z. Tang, Z. Wen, C. Chang, C. Wang, D.Sun, Y. Ye, D. Qiu, Y. Ke, F. Liu, and Z. Yang. Scalable Synthesis of Photoluminescent Single-Chain Nanoparticles by Electrostatic-Mediated Intramolecular Crosslinking. Angew. Chem. Int. Ed. 2022, 61, e202205183” discloses a method of first modifying a polymer with a fluorescent motif, and then adding a photocrosslinker to induce intrachain crosslinking of the polymer to obtain fluorescent single-chain polymer nanoparticles. This method for preparing fluorescent single-chain polymer nanoparticles requires more than two chemical reaction steps, and the introduced fluorescent motif will affect the intrachain folding and crosslinking of the polymer. Summary of the invention

[0005] The main purpose of the present application is to provide a "one-step" preparation method for fluorescent single-chain polymer nanoparticles, aiming to achieve a one-step method for simply preparing fluorescent single-chain polymer nanoparticles.

[0006] To achieve the above purpose, the present application provides a fluorescent single-chain polymer nanoparticle, the structural formula of which is: .

[0007] Optionally, in the structural formula, x+y=1.

[0008] To achieve the above objectives, the present application also provides a "one-step" preparation method of fluorescent single-chain polymer nanoparticles, comprising: Dissolving polyethylene glycol methyl ether methacrylate, cyanostilbene methacrylate monomer and an initiator in a ninth solvent to obtain a reaction solution, and subjecting the reaction solution to a polymerization reaction under a nitrogen environment to obtain poly((Z)-2-(2-(2-(2-(4-(2-cyano-2-(3,4,5-tri(dodecyloxy)phenyl)vinyl)hydroxyethoxy)ethoxy)ethoxy)ethoxy)ethyl methacrylate-polyethylene glycol methyl ether methacrylate); Poly((Z)-2-(2-(2-(2-(4-(2-cyano-2-(3,4,5-tri(dodecyloxy)phenyl)vinyl)hydroxyethoxy)ethoxy)ethoxy)ethoxy)ethyl methacrylate-polyethylene glycol methyl ether methacrylate) is dissolved in water to obtain a copolymer solution, the copolymer solution is irradiated under an ultraviolet lamp, and separated by freeze-drying to obtain fluorescent single-chain polymer nanoparticles.

[0009] Optionally, the preparation method of cyanostilbene methacrylate monomer comprises: Dissolving 3,4,5-trihydroxybenzaldehyde, 1-bromododecane, tetrabutylammonium iodide and potassium carbonate in a first solvent, and performing a first substitution reaction to obtain 3,4,5-tri(dodecyloxy)benzaldehyde; Dissolving 3,4,5-tri(dodecyloxy)benzaldehyde in a second solvent to obtain a 3,4,5-tri(dodecyloxy)benzaldehyde solution, adding a lithium aluminum hydride solution dropwise to the 3,4,5-tri(dodecyloxy)benzaldehyde solution, and performing a reduction reaction to obtain 3,4,5-tri(dodecyloxy)benzyl alcohol; 3, 4, 5-tri(dodecyloxy)benzyl alcohol is dissolved in a third solvent to obtain a 3, 4, 5-tri(dodecyloxy)benzyl alcohol solution, a phosphorus tribromide solution is added dropwise to the 3, 4, 5-tri(dodecyloxy)benzyl alcohol solution, and a second substitution reaction is performed to obtain 5-(bromomethyl)-1,2,3-tri(dodecyloxy)benzene; 5-(bromomethyl)-1,2,3-tri(dodecyloxy)benzene, trimethylsilyl cyanide and tetrabutylammonium fluoride are dissolved in a fourth solvent and subjected to a first nucleophilic substitution reaction to obtain 3,4,5-tri(dodecyloxy)benzeneacetonitrile; dissolving tetraethylene glycol and triethylamine in a fifth solvent to obtain a first mixed solution, dropping a 4-toluenesulfonyl chloride solution into the first mixed solution, and performing a second nucleophilic substitution reaction to obtain p-toluenesulfonate-tetraethylene glycol; Dissolving p-toluenesulfonate-tetraethylene glycol, p-hydroxybenzaldehyde and carbonic acid in a sixth solvent, and subjecting to a first nucleophilic addition reaction to obtain 4-(2-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)ethoxy)benzaldehyde; Dissolving 3,4,5-tri(dodecyloxy)benzeneacetonitrile and 4-(2-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)ethoxy)ethoxy)benzaldehyde in a seventh solvent, and subjecting to a second nucleophilic addition reaction and a dehydration reaction to obtain (Z)-3-(4-(2-(2-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)ethoxy)phenyl)-2-(3,4,5-tri(dodecyloxy)phenyl)acrylonitrile; (Z)-3-(4-(2-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)ethoxy)phenyl)-2-(3,4,5-tri(dodecyloxy)phenyl)acrylonitrile and triethylamine are dissolved in an eighth solvent to obtain a second mixed solution, methacryloyl chloride solution is added dropwise to the second mixed solution, and a third nucleophilic substitution reaction is performed to obtain cyanobenzene methacrylate monomer.

[0010] Optionally, in the first substitution reaction, the molar ratio of 3,4,5-trihydroxybenzaldehyde, 1-bromododecane, tetrabutylammonium iodide and potassium carbonate is 1:3:0.1:(3~1):5:0.2:8, the reaction temperature is 80~85°C, and the reaction time is 12-24h; in the reduction reaction, the molar ratio of 3,4,5-tri(dodecyloxy)benzaldehyde and lithium aluminum hydride in the lithium aluminum hydride solution is 1:1~2, the dropwise addition temperature is -5~5°C, and the reaction conditions are: react at -5~5°C for 0.5~1h and then react at 20~30°C for 2~3h; in the second substitution reaction, 3, 4, The molar ratio of 5-tri(dodecyloxy)benzyl alcohol to phosphorus tribromide in the phosphorus tribromide solution is 1:1~2, the dropping temperature is -5~5°C, the reaction temperature is 20~30°C, and the reaction time is 3~4h; in the first nucleophilic substitution reaction, the molar ratio of 5-(bromomethyl)-1,2,3-tri(dodecyloxy)benzene, trimethylsilyl cyanide and tetrabutylammonium fluoride is 1:1.2:0.2~1:1.5:1.5, the reaction temperature is 20~30°C, and the reaction time is 3~4h.

[0011] Optionally, in the second nucleophilic substitution reaction, the molar ratio of 4-toluenesulfonyl chloride, tetraethylene glycol and triethylamine in the reaction solution is 1:1:(1.1-4):1:1.2, the dropping temperature is -5-5°C, the reaction temperature is 20-30°C, and the reaction time is 0.5-1h; in the first nucleophilic addition reaction, the molar ratio of p-toluenesulfonate-tetraethylene glycol, p-hydroxybenzaldehyde and carbonic acid is 1:1:(2-1.1):1:3, the reaction temperature is 80-85°C, and the reaction time is 12-24h; in the second nucleophilic addition reaction, the molar ratio of 3,4,5-tri(dodecyloxy)benzyl cyanide and 4-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)ethoxy)ethoxy)benzaldehyde is 1-1.2:1, the reaction temperature is 40-50°C, and the reaction time is 12-24h; In the third nucleophilic substitution reaction, the molar ratio of (Z)-3-(4-(2-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)ethoxy)phenyl)-2-(3,4,5-tri(dodecyloxy)phenyl)acrylonitrile, triethylamine and methacryloyl chloride solution is 1:1:(1.5~1):3:3, the dropping temperature is -5~5°C, the reaction temperature is 20~30°C, and the reaction time is 12~24h.

[0012] Optionally, the first solvent is N,N-dimethylformamide solution, the second solvent is tetrahydrofuran solution, the third solvent is dichloromethane solution, and the fourth solvent is acetonitrile; the fifth solvent is dichloromethane solution, the sixth solvent is N,N-dimethylformamide solution, the seventh solvent is a mixed solution of ethanol and tetrabutylammonium hydroxide, the volume ratio of ethanol to tetrabutylammonium hydroxide is 20~30:1, and the eighth solvent is dichloromethane solution.

[0013] Optionally, before the polymerization reaction, the reaction solution is subjected to a freeze-vacuum-thaw cycle in a nitrogen environment; and after the polymerization reaction, the reaction product is separated and purified.

[0014] Optionally, the reaction temperature of the polymerization reaction is 73-76° C., the reaction time is 10-12 h under stirring; the ninth solvent is tetrahydrofuran solution; the wavelength of the ultraviolet lamp is 365 nm, and the irradiation time is 6-12 h.

[0015] To achieve the above objectives, the present application also provides an application of fluorescent single-chain polymer nanoparticles in catalysts, biosensors, nanoreactors or nanomedicines.

[0016] Compared with the prior art, the present invention has the following beneficial effects: The present invention provides a one-step preparation method for fluorescent single-chain polymer nanoparticles. First, hydrophobic cyanophenylvinyl methacrylate monomer ((Z)-2-(2-(2-(2-(4-(2-cyano-2- A random copolymer is obtained by copolymerizing (3,4,5-tri(dodecyloxy)phenyl)vinyl)hydroxyethoxy)ethoxy)ethoxy)ethoxy)ethyl methacrylate) with a hydrophilic polyethylene glycol monomethyl ether methacrylate monomer. In the single-chain aggregation state of this random copolymer, the hydrophobic cyanostyrene moiety can simultaneously have two states: ordered stacking and single-molecule dispersion. The ordered stacked cyanostyrene moiety undergoes intermolecular [2+2] cycloaddition under light conditions, and cross-linking within the polymer chain can be achieved without the addition of an additional cross-linking agent; while the dispersed cyanostyrene moiety undergoes intramolecular cyclization under light conditions to produce phenanthrene derivatives with strong fluorescent properties, and strong fluorescent properties can be achieved without post-modification of the fluorescent moiety, thereby realizing the "one-step" preparation of fluorescent polymer single-chain nanoparticles; at the same time, the "one-step" preparation method of this fluorescent polymer single-chain nanoparticle can simulate the changes in structure and function during protein folding. BRIEF DESCRIPTION OF THE DRAWINGS

[0017] Figure 1 A schematic diagram of the molecular folding of a single-chain polymer prepared by a "one-step" preparation method of fluorescent single-chain polymer nanoparticles in this application; Figure 2An atomic force microscope image of a single-chain polymer prepared by a "one-step" preparation method for fluorescent single-chain polymer nanoparticles of this application; Figure 3 This is a comparison chart of gel permeation chromatography of a single-chain polymer prepared by a "one-step" preparation method of fluorescent single-chain polymer nanoparticles in this application before and after illumination; Figure 4 A schematic diagram of the change in fluorescence spectrum of a single-chain polymer prepared by a "one-step" preparation method for fluorescent single-chain polymer nanoparticles in this application under ultraviolet light irradiation.

[0018] The realization of the purpose, functional features and advantages of this application will be further explained in conjunction with embodiments and with reference to the accompanying drawings. DETAILED DESCRIPTION

[0019] In order to make the purpose, technical solutions and advantages of this application clearer, the technical solutions in this application will be clearly and completely described below in conjunction with the drawings in this application. Obviously, the described embodiments are part of the embodiments of this application, not all of them. Based on the embodiments in this application, all other embodiments obtained by ordinary technicians in this field without creative work are within the scope of protection of this application.

[0020] The first embodiment of the present invention provides a fluorescent single-chain polymer nanoparticle, which is a viscous yellow solid and has the structural formula:

[0021] Among them, x+y=1.

[0022] The second embodiment of the present invention provides a one-step preparation method of fluorescent single-chain polymer nanoparticles, the preparation method comprising: Step S1, dissolving polyethylene glycol methyl ether methacrylate, cyanophenylvinyl methacrylate monomer and initiator in a ninth solvent to obtain a reaction solution, placing the reaction solution in a dry Schlenk tube in a nitrogen environment to perform freeze-vacuum-thaw cycles for multiple times, and then continuing to stir at 73-76° C. for 10-12 hours to perform a polymerization reaction; after the reaction is completed, separating and purifying by column chromatography to obtain poly((Z)-2-(2-(2-(2-(4-(2-cyano-2-(3,4,5-tri(dodecyloxy)phenyl)vinyl)hydroxyethoxy)ethoxy)ethoxy)ethoxy)ethyl methacrylate-polyethylene glycol methyl ether methacrylate); wherein the ninth solvent may be a tetrahydrofuran solution; Step S2, dissolving poly((Z)-2-(2-(2-(2-(4-(2-cyano-2-(3,4,5-tri(dodecyloxy)phenyl)vinyl)hydroxyethoxy)ethoxy)ethoxy)ethoxy)ethyl methacrylate-polyethylene glycol methyl ether methacrylate) in water to obtain a copolymer solution, irradiating the copolymer solution under an ultraviolet lamp with a wavelength of 365 nm for 6 to 12 h, and separating by freeze-drying to obtain fluorescent single-chain polymer nanoparticles.

[0023] In this embodiment, a random copolymer is obtained by copolymerizing a hydrophobic cyanostyrene methacrylate monomer with a hydrophilic polyethylene glycol monomethyl ether methacrylate monomer; in the single-chain aggregation state of this random copolymer, the hydrophobic cyanostyrene motifs can simultaneously have two states: ordered stacking and single-molecule dispersion, wherein the ordered stacked cyanostyrene motifs undergo intermolecular [2+2] cycloaddition under illumination conditions, which can achieve crosslinking within the polymer chain; and the dispersed cyanostyrene motifs undergo intramolecular cyclization under illumination conditions to produce phenanthrene derivatives with strong fluorescent properties, thereby achieving the "one-step" preparation of fluorescent polymer single-chain nanoparticles. This "one-step" preparation method of fluorescent polymer single-chain nanoparticles can not only simulate the changes in structure and function during protein folding. Molecular folding demonstration of fluorescent single-chain polymer nanoparticles Figure 1 ,from Figure 1 It can be seen that the synthesized copolymer first pre-collapses in water to form loose nanospheres. Under the irradiation of 365 nm ultraviolet light, the orderly stacked cyanostyrene moieties undergo intermolecular [2+2] cycloaddition under light conditions, which can achieve cross-linking within the polymer chain; while the dispersed cyanostyrene moieties undergo intramolecular cyclization under light conditions to produce phenanthrene derivatives with strong fluorescent properties, successfully preparing strong fluorescent single-chain polymer nanoparticles.

[0024] The method for preparing cyanophenylvinyl methacrylate monomer in step S1 specifically comprises the following steps: Step S11, dissolving 3,4,5-trihydroxybenzaldehyde, 1-bromododecane, tetrabutylammonium iodide and potassium carbonate in a molar ratio of 1:3:0.1:(3~1):5:0.2:8 in a first solvent, stirring to carry out a first substitution reaction, the reaction temperature is 80~85°C, and the reaction time is 12-24h; after the reaction liquid is cooled to room temperature, a product is obtained, and the product of the substitution reaction is purified, and the specific process is: low-pressure evaporation to remove the N,N-dimethylformamide solvent, followed by extraction with dichloromethane, and then drying with anhydrous magnesium sulfate and rotary evaporation to remove the solvent, and then separation and purification by column chromatography to obtain a white solid 3,4,5-tri(dodecyloxy)benzaldehyde; wherein the first solvent can be an N,N-dimethylformamide solution.

[0025] Among them, the bromine atoms in bromoalkanes are easily replaced by other polar groups under polar conditions (such as alkaline environment). Due to the strong ability of bromine atoms to attract electrons, the C-Br bond has a certain polarity. When this polar bond encounters the hydroxyl group of 3,4,5-trihydroxybenzaldehyde, the bromine atom can be replaced by the hydroxyl group. Potassium carbonate provides an alkaline environment, and tetrabutylammonium iodide serves as a phase transfer catalyst. If the ratio of 1-bromododecane to 3,4,5-trihydroxybenzaldehyde is less than 3:1, the hydroxyl group will not be completely replaced, and 1- or 2-substituted products are easily obtained.

[0026] Step S12, 3, 4, 5-tri(dodecyloxy)benzaldehyde and lithium aluminum hydride in a molar ratio of 1:1~2 are dissolved in a second solvent to obtain a 3, 4, 5-tri(dodecyloxy)benzaldehyde solution and a lithium aluminum hydride solution, and the lithium aluminum hydride solution is slowly added dropwise to the above benzaldehyde derivative solution at -5~5°C and stirred for reduction reaction. During the reaction, the mixture is first stirred in an ice bath for 0.5~1h and then stirred at room temperature for 2~3h. After the reaction is completed, water is added to quench the reaction and purification is performed. The specific process is: low-pressure distillation to remove the second solvent, followed by extraction with dichloromethane, and then drying with anhydrous magnesium sulfate and rotary evaporation to remove the solvent, and then separation and purification by column chromatography to obtain a white solid 3,4,5-tri(dodecyloxy)benzyl alcohol; wherein the second solvent can be a tetrahydrofuran solution.

[0027] Among them, the carbonyl group of the benzaldehyde derivative first undergoes a nucleophilic addition reaction with the hydroxide ion to form a benzyl alcohol anion intermediate. Subsequently, the hydride anion is transferred from the lithium aluminum hydride to the benzyl alcohol anion intermediate to form benzyl alcohol and lithium salt. Lithium aluminum hydride is used as an alkaline reducing agent. If the ratio is less than 1:1, the benzaldehyde derivative cannot be completely reduced. If the ratio is greater than 1:2, the benzaldehyde is easily over-reduced to generate by-products such as methyl compounds.

[0028] Step S13, dissolving 3, 4, 5-tri(dodecyloxy)benzyl alcohol and phosphorus tribromide in a molar ratio of 1:1~2 in a third solvent to obtain a 3, 4, 5-tri(dodecyloxy)benzyl alcohol solution and a phosphorus tribromide solution, slowly dropping the phosphorus tribromide solution into the above-mentioned benzyl alcohol derivative solution at -5~5°C, stirring to carry out a second substitution reaction, the reaction temperature is room temperature, and the reaction time is 3~4h; after the reaction is completed, adding water to quench the reaction and purifying, the specific process is: extracting the reaction solution after adding water with dichloromethane, then drying with anhydrous magnesium sulfate and rotary evaporating to remove the solvent, and then separating and purifying by column chromatography to obtain a white solid 5-(bromomethyl)-1,2,3-tri(dodecyloxy)benzene; wherein the third solvent can be a dichloromethane solution.

[0029] The hydroxyl group of the benzyl alcohol derivative is replaced by a bromine atom to generate bromobenzene. Phosphorus tribromide serves as a bromine donor and catalyst.

[0030] Step S14, dissolving 5-(bromomethyl)-1,2,3-tri(dodecyloxy)benzene, trimethylsilyl cyanide and tetrabutylammonium fluoride in a molar ratio of 1:1.2:(0.2-1):1.5:1.5 in a fourth solvent, stirring at room temperature for a first nucleophilic substitution reaction, the reaction time is 3-4 h; after the reaction is completed, purification is performed, the specific process is: first removing the fourth solvent, then extracting with dichloromethane, then drying with anhydrous magnesium sulfate and rotary evaporation to remove the solvent, and then separating and purifying by column chromatography to obtain a white solid 3,4,5-tri(dodecyloxy)benzeneacetonitrile; wherein the fourth solvent can be acetonitrile.

[0031] Among them, tetrabutylammonium fluoride releases fluoride ions to break the carbon-silicon bond and activate trimethylsilyl cyanide to release cyanide ions, and then the cyanide ions react with bromobenzene in an SN2 nucleophilic substitution reaction, and bromine is replaced by cyano to generate a benzyl cyanide derivative. Trimethylsilyl cyanide provides cyano groups, and tetrabutylammonium fluoride acts as a phase transfer catalyst.

[0032] Step S15, dissolving tetraethylene glycol and triethylamine in a fifth solvent to obtain a first mixed solution, dissolving 4-toluenesulfonyl chloride in a fifth solvent to obtain a 4-toluenesulfonyl chloride solution, and dropping the 4-toluenesulfonyl chloride solution into the first mixed solution at -5~5°C, wherein the molar ratio of tetraethylene glycol, 4-toluenesulfonyl chloride and triethylamine dissolved in dichloromethane is 1:1:(1.1~4):1:1.2, and after the dropwise addition is completed, stirring is continued at room temperature to carry out a second nucleophilic substitution reaction (SN2), and the reaction time is 0.5~1h; after the reaction is completed, purification is carried out, and the specific process is: adding sodium bicarbonate to neutralize the pH, extracting with dichloromethane, then drying with anhydrous magnesium sulfate, and then rotary evaporating to remove the solvent, and then separating and purifying by column chromatography to obtain an oily liquid p-toluenesulfonate-tetraethylene glycol; wherein the fifth solvent can be a dichloromethane solution.

[0033] The hydroxyl group of tetraethylene glycol acts as a nucleophile to attack the sulfur atom of 4-toluenesulfonyl chloride to generate p-toluenesulfonate-tetraethylene glycol, while triethylamine acts as a base to capture the byproduct hydrogen chloride to prevent the system from acidifying. Tetraethylene glycol has a dihydroxyl site, so in order to achieve monohydroxy esterification, an excess of tetraethylene glycol is required.

[0034] Step S16, dissolving p-toluenesulfonate-tetraethylene glycol, p-hydroxybenzaldehyde and potassium carbonate in a molar ratio of 1:1:(2-1.1):1:3 in a sixth solvent and stirring to carry out a first nucleophilic addition reaction, the reaction temperature is 80-85°C, and the reaction time is 12-24 hours; after the reaction liquid is cooled to room temperature, it is purified, and the specific process is: removing the sixth solvent, then extracting with dichloromethane, and then drying with anhydrous magnesium sulfate and rotary evaporation to remove the solvent, and then separating and purifying by column chromatography to obtain an oily liquid 4-(2-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)ethoxy)ethoxy)benzaldehyde; wherein the sixth solvent can be an N,N-dimethylformamide solution.

[0035] Here, the hydroxyl group acts as a nucleophile to attack the carbonyl carbon of p-toluenesulfonate to form an intermediate, and then the sulfonate group is released as a leaving group.

[0036] Step S17, dissolving 3,4,5-tri(dodecyloxy)benzyl nitrile and 4-(2-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)ethoxy)benzaldehyde in a molar ratio of 1 to 1.2:1 in a seventh solvent, wherein the seventh solvent is a mixed solution of ethanol and tetrabutylammonium hydroxide in a volume ratio of 20 to 30:1, stirring for a second nucleophilic addition reaction and a dehydration reaction, the reaction temperature is 40 to 50°C, and the reaction time is 12 to 24 hours; after the reaction is completed, purification is performed, and the specific process is: first removing the seventh solvent, then extracting with dichloromethane, then drying with anhydrous magnesium sulfate and rotary evaporation to remove the solvent, and then separating and purifying by column chromatography to obtain a yellow solid (Z)-3-(4-(2-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)ethoxy)ethoxy)phenyl) -2-(3,4,5-tri(dodecyloxy)phenyl)acrylonitrile; wherein the seventh solvent may be a mixed solution of ethanol and tetrabutylammonium hydroxide, and the volume ratio of ethanol to tetrabutylammonium hydroxide is 20~30:1.

[0037] Among them, the carbon atom near the alkynyl hydrogen atom in the benzyl cyanocyanide derivative acts as a nucleophile to attack the carbonyl carbon in the benzaldehyde derivative to form a four-membered ring intermediate. The resulting intermediate forms the double bond of cyanobenzene through a dehydration reaction (generating a molecule of water). This process involves the removal of hydroxide ions.

[0038] Step S18, dissolving (Z)-3-(4-(2-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)ethoxy)phenyl)-2-(3,4,5-tri(dodecyloxy)phenyl)acrylonitrile and triethylamine in an eighth solvent to obtain a second mixed solution, dissolving methacrylic chloride in the eighth solvent to obtain a methacrylic chloride solution, and (Z)-3-(4-(2-(2-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)ethoxy)phenyl)-2-(3,4,5-tri(dodecyloxy)phenyl)acrylonitrile and triethylamine in an eighth solvent to obtain a second mixed solution. -2-(3,4,5-tri(dodecyloxy)phenyl)acrylonitrile, methacryloyl chloride and triethylamine in a molar ratio of 1:3:3; slowly drop the methacryloyl chloride solution into the acrylonitrile derivative solution at -5~5°C, stir at room temperature after the dropwise addition to carry out the third nucleophilic substitution reaction, the reaction time is 12h; after the reaction is completed, add water to quench the reaction and then purify, the specific process is: extract with dichloromethane, then dry with anhydrous magnesium sulfate and remove the solvent by rotary evaporation, and then separate and purify by column chromatography to obtain a yellow solid (Z)-2-(2-(2-(2-(4-(2-cyano-2- (3,4,5-tri(dodecyloxy)phenyl)vinyl)hydroxyethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethyl methacrylate, that is, cyano distilbene methacrylate monomer, wherein the eighth solvent can be a dichloromethane solution. The structural formula of cyano distilbene methacrylate monomer is:

[0039] The second embodiment of the present invention provides an application of fluorescent single-chain polymer nanoparticles in catalysts, biosensors, nanoreactors or nanomedicines.

[0040] Example 1 Step S10, 1.8 g methyl 3,4,5-trihydroxybenzoate, 9.74 g 1-bromododecane, 0.1 g tetrabutylammonium iodide, 10.7 g K 2 CO 3 , 50 mL of N,N-dimethylformamide was added to a 100 mL eggplant-shaped bottle, and the reaction was stirred at a constant temperature of 80 °C overnight. After the reaction was completed, most of the N,N-dimethylformamide solvent was removed by vacuum distillation after cooling to room temperature, and then extracted with 50 mL of dichloromethane 2-3 times, and then dried over anhydrous magnesium sulfate and rotary evaporated to remove the solvent, and then separated and purified by column chromatography (eluent is n-hexane: ethyl acetate = 5:1) to obtain purified white solid 3,4,5-tri(dodecyloxy)benzaldehyde; Step S20, add 6.2 g 3,4,5-trihydroxybenzaldehyde and 20 mL tetrahydrofuran to the reaction bottle, stir at 0 ° C for 20 min, add 13 mL of lithium aluminum hydride tetrahydrofuran solution to the constant pressure dropping funnel, slowly drip into the eggplant-shaped bottle (control the dropping time for 1h), continue to stir in an ice bath for 30min, then transfer to room temperature and continue stirring for 2h. Monitor the progress of the reaction by thin layer chromatography. After the reaction is completed, slowly add a small amount of water to quench, and remove most of the solvent by vacuum distillation. Extract with dichloromethane 3 times, then dry over anhydrous magnesium sulfate and rotary evaporate to remove the solvent, and collect the clean product white solid 3,4,5-tri(dodecyloxy)benzyl alcohol; Step S30, add 4.2 g 3,4,5-tri(dodecyloxy)benzyl alcohol and 20 mL dichloromethane to an eggplant-shaped bottle, stir at 0°C for 20 min, add 1.4 mL of tetrahydrofuran solution of phosphorus tribromide to a constant pressure dropping funnel, slowly drip into the eggplant-shaped bottle, and control the dropping time to 2h. After the dropwise addition is completed, transfer to room temperature and continue stirring for 3h. Monitor the progress of the reaction by thin layer chromatography. After the reaction is completed, slowly add a small amount of water to quench, extract twice with dichloromethane, then dry over anhydrous magnesium sulfate and rotary evaporate to remove the solvent to obtain a white solid 5-(bromomethyl)-1,2,3-tri(dodecyloxy)benzene; Step S40, add 3.7 g 5-(bromomethyl)-1,2,3-tri(dodecyloxy)benzene, 30 mL acetonitrile, and 1.2 mL trimethylsilyl cyanide into an eggplant-shaped bottle and stir at room temperature for 3 h. Monitor the progress of the reaction by thin layer chromatography. After the reaction is completed, most of the solvent is removed by vacuum distillation, extracted twice with dichloromethane, then dried over anhydrous magnesium sulfate and rotary evaporated to remove the solvent, and then separated and purified by column chromatography (eluent is dichloromethane) to obtain a white solid 3,4,5-tri(dodecyloxy)benzeneacetonitrile; Step S50, add 6 g of tetraethylene glycol, 3.9 mL of triethylamine, and 20 mL of dichloromethane into an eggplant-shaped bottle, stir at 0°C for 20 min, add 1.47 g of 4-toluenesulfonyl chloride and 20 mL of dichloromethane solution into a constant pressure dropping funnel, slowly drip into the eggplant-shaped bottle, control the dropping time to 30 min, and continue to stir at room temperature for 0.5 to 1 h after the dropwise addition is completed; after the reaction is completed, add sodium bicarbonate, extract with dichloromethane twice, then dry with anhydrous magnesium sulfate and rotary evaporate to remove the solvent, and then separate and purify by column chromatography to obtain an oily liquid p-toluenesulfonate-tetraethylene glycol; Step S60, dissolving 1.57 g of p-toluenesulfonate-tetraethylene glycol, 0.52 g of p-hydroxybenzaldehyde and 1.19 g of carbonic acid in N,N-dimethylformamide, stirring at 85° C. for overnight reaction; after the reaction solution is cooled to room temperature, evaporating at low pressure to remove the N,N-dimethylformamide solvent, then extracting with dichloromethane three times, and then drying over anhydrous magnesium sulfate and rotary evaporating to remove the solvent, and then separating and purifying by column chromatography to obtain an oily liquid 4-(2-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)ethoxy)benzaldehyde; Step S70, add 0.5 g of 3,4,5-tri(dodecyloxy)benzeneacetonitrile, 30 mL of a mixed solvent of ethanol and tetrabutylammonium hydroxide (25:1) into an eggplant-shaped bottle, slowly heat to 50° C. until the solution is completely dissolved and clarified, add 1.12 g of 4-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)ethoxy)ethoxy)benzaldehyde, stir and react at 40° C. overnight; after the reaction is completed, remove the solvent by low-pressure distillation, then extract with dichloromethane 3 times, then dry over anhydrous magnesium sulfate and remove the solvent by rotary evaporation, and then separate and purify by column chromatography to obtain a yellow solid (Z)-3-(4-(2-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)ethoxy)phenyl)-2-(3,4,5-tri(dodecyloxy)phenyl)acrylonitrile; Step S80, 1.18 g (Z)-3-(4-(2-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)ethoxy)phenyl)-2-(3,4,5-tri(dodecyloxy)phenyl)acrylonitrile, 0.52 ml triethylamine and 30 mL anhydrous dichloromethane were dissolved, 0.39 methacryloyl chloride and 30 mL anhydrous dichloromethane were added to a constant pressure dropping funnel, and the mixture was slowly dripped into an eggplant-shaped bottle, and the dropping time was controlled to 8 h. After the dropping was completed, stirring was continued at room temperature overnight; after the reaction was completed, water was added to quench the reaction, and the mixture was extracted with dichloromethane 3 times, and then dried over anhydrous magnesium sulfate and the solvent was removed by rotary evaporation, and then separated and purified by column chromatography to obtain a yellow solid (Z)-2-(2-(2-(2-(4-(2-cyano-2- (3,4,5-tri(dodecyloxy)phenyl)vinyl)hydroxyethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethyl methacrylate.

[0041] Example 2 Step S90, 0.12 g of polyethylene glycol methyl ether methacrylate, 0.1 g of (Z)-2-(2-(2-(2-(4-(2-cyano-2-(3,4,5-tri(dodecyloxy)phenyl)vinyl)hydroxyethoxy)ethoxy)ethoxy)ethoxy)ethyl methacrylate and 0.01 g of AIBN are dissolved in tetrahydrofuran solution, and the mixed solution is subjected to three freeze-vacuum-thaw cycles in a dry Schlenk tube in a nitrogen environment, and then stirred at 75° C. for 12 hours; after the reaction is completed, the mixture is separated and purified by column chromatography to obtain a viscous yellow water-soluble copolymer, i.e., poly((Z)-2-(2-(2-(4-(2-cyano-2-(3,4,5-tri(dodecyloxy)phenyl)vinyl)hydroxyethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethyl methacrylate-polyethylene glycol methyl ether methacrylate); Step S100, dissolving 1 g of the water-soluble copolymer prepared in step S90 in 1 mL of ultrapure water, ultrasonicating until the solution is clear, then moving the solution to 365 nm ultraviolet light and irradiating it at room temperature for 6 h, and freeze-drying and separation to obtain viscous yellow solid fluorescent single-chain polymer nanoparticles, whose chemical formula has x=0.8, y=0.2.

[0042] The atomic force microscopy image of the fluorescent single-chain polymer nanoparticles prepared in this example is shown in Figure 2 As can be seen from the figure, the single-chain polymer nanoparticles have been successfully obtained in this embodiment; and the products obtained in this embodiment were compared by gel permeation chromatography, and the results are shown in Figure 3 ,from Figure 3 It can be seen that single-chain polymer nanoparticles have been successfully obtained in this embodiment. Figure 4 It can be seen from the graph of the fluorescence intensity changing with the irradiation time that the single-chain polymer nanoparticles prepared in Example 1 exhibit strong green light emission.

[0043] Example 3 Step S10, 2 g of methyl 3,4,5-trihydroxybenzoate, 12.2 g of 1-bromododecane, 0.6 g of tetrabutylammonium iodide, 7.6 g of K 2 CO 3 , 50 mL of N,N-dimethylformamide was added to a 100 mL eggplant-shaped bottle, and the reaction was stirred at a constant temperature of 85 °C overnight. After the reaction was completed, most of the N,N-dimethylformamide solvent was removed by vacuum distillation after cooling to room temperature, and then extracted with 50 mL of dichloromethane 2-3 times, and then dried over anhydrous magnesium sulfate and rotary evaporated to remove the solvent, and then separated and purified by column chromatography (eluent is n-hexane: ethyl acetate = 5:1) to obtain purified white solid 3,4,5-tri(dodecyloxy)benzaldehyde; Step S20, add 7 g 3,4,5-trihydroxybenzaldehyde and 20 mL tetrahydrofuran to the reaction bottle, stir at 0 ° C for 20 min, add 45 mg of lithium aluminum hydride tetrahydrofuran solution to the constant pressure dropping funnel, slowly drip into the eggplant-shaped bottle (control the dropping time for 1h), continue to stir in an ice bath for 1h, then transfer to room temperature and continue stirring for 3h. Monitor the progress of the reaction by thin layer chromatography. After the reaction is completed, slowly add a small amount of water to quench, and remove most of the solvent by vacuum distillation. Extract with dichloromethane 3 times, then dry over anhydrous magnesium sulfate and rotary evaporate to remove the solvent, and collect the clean product white solid 3,4,5-tri(dodecyloxy)benzyl alcohol; Step S30, add 10 g 3,4,5-tri(dodecyloxy)benzyl alcohol and 20 mL dichloromethane to an eggplant-shaped bottle, stir at 0°C for 20 min, add 2.1 mL of tetrahydrofuran solution of phosphorus tribromide to a constant pressure dropping funnel, slowly drip into the eggplant-shaped bottle, and control the dropping time to 2.5 h. After the dropwise addition is completed, transfer to room temperature and continue stirring for 4 h. Monitor the progress of the reaction by thin layer chromatography. After the reaction is completed, slowly add a small amount of water to quench, extract twice with dichloromethane, and then dry over anhydrous magnesium sulfate and rotary evaporate to remove the solvent to obtain a white solid 5-(bromomethyl)-1,2,3-tri(dodecyloxy)benzene; Step S40, add 4.1 g 5-(bromomethyl)-1,2,3-tri(dodecyloxy)benzene and 30 mL acetonitrile to an eggplant-shaped bottle and fully dissolve, then drop 0.85 mL trimethylsilyl cyanide and 0.3 g tetrabutylammonium fluoride into the eggplant-shaped bottle, and stir at room temperature for 5 hours. Monitor the progress of the reaction by thin layer chromatography. After the reaction is completed, most of the solvent is removed by vacuum distillation, extracted twice with dichloromethane, then dried over anhydrous magnesium sulfate and rotary evaporated to remove the solvent, and then separated and purified by column chromatography (eluent is dichloromethane) to obtain a white solid 3,4,5-tri(dodecyloxy)benzeneacetonitrile; Step S50, add 6 g of tetraethylene glycol, 1.57 mL of triethylamine, and 20 mL of dichloromethane into an eggplant-shaped bottle, stir at 0°C for 20 min, add 1.95 g of 4-toluenesulfonyl chloride and 20 mL of dichloromethane solution into a constant pressure dropping funnel, slowly drip into the eggplant-shaped bottle, control the dropping time to 2 h, and continue stirring at room temperature for 0.5 to 1 h after the dropwise addition is completed; after the reaction is completed, add sodium bicarbonate, extract with dichloromethane twice, then dry with anhydrous magnesium sulfate and rotary evaporate to remove the solvent, and then separate and purify by column chromatography to obtain an oily liquid p-toluenesulfonate-tetraethylene glycol; Step S60, dissolving 1.5 g of p-toluenesulfonate-tetraethylene glycol, 0.45 g of p-hydroxybenzaldehyde and 1.55 g of carbonic acid in N,N-dimethylformamide, stirring and reacting at 80° C. overnight; after the reaction solution is cooled to room temperature, evaporating at low pressure to remove the N,N-dimethylformamide solvent, then extracting with dichloromethane three times, and then drying over anhydrous magnesium sulfate and rotary evaporating to remove the solvent, and then separating and purifying by column chromatography to obtain an oily liquid 4-(2-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)ethoxy)benzaldehyde; Step S70, add 0.5 g of 3,4,5-tri(dodecyloxy)benzeneacetonitrile, 30 mL of a mixed solvent of ethanol and tetrabutylammonium hydroxide (25:1) into an eggplant-shaped bottle, slowly heat to 50° C. until the solution is completely dissolved and clarified, add 0.94 g of 4-(2-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)ethoxy)ethoxy)benzaldehyde, stir and react overnight at 45° C.; after the reaction, remove the solvent by low-pressure distillation, then extract with dichloromethane 3 times, then dry over anhydrous magnesium sulfate and remove the solvent by rotary evaporation, and then separate and purify by column chromatography to obtain a yellow solid (Z)-3-(4-(2-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)ethoxy)ethoxy)phenyl)-2-(3,4,5-tri(dodecyloxy)phenyl)acrylonitrile; Step S80, 1.18 g (Z)-3-(4-(2-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)ethoxy)phenyl)-2-(3,4,5-tri(dodecyloxy)phenyl)acrylonitrile, 0.52 ml triethylamine and 30 mL anhydrous dichloromethane were dissolved, 0.32 g methacryloyl chloride and 30 mL anhydrous dichloromethane were added to a constant pressure dropping funnel, and the mixture was slowly dripped into an eggplant-shaped bottle, and the dropping time was controlled to 8 h. After the dropping was completed, stirring was continued at room temperature overnight; after the reaction was completed, water was added to quench the reaction, and the mixture was extracted with dichloromethane 3 times, and then dried over anhydrous magnesium sulfate and the solvent was removed by rotary evaporation, and then separated and purified by column chromatography to obtain a yellow solid (Z)-2-(2-(2-(2-(4-(2-cyano-2- (3,4,5-tri(dodecyloxy)phenyl)vinyl)hydroxyethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethyl methacrylate.

[0044] Example 4 Step S90, 0.09 g of polyethylene glycol methyl ether methacrylate, 0.15 g of (Z)-2-(2-(2-(2-(4-(2-cyano-2-(3,4,5-tri(dodecyloxy)phenyl)vinyl)hydroxyethoxy)ethoxy)ethoxy)ethoxy)ethyl methacrylate and 0.007 g of AIBN are dissolved in tetrahydrofuran solution, and the mixed solution is subjected to three freeze-vacuum-thaw cycles in a dry Schlenk tube in a nitrogen environment, and then stirred at 70° C. for 20 hours; after the reaction is completed, the mixture is separated and purified by column chromatography to obtain a viscous yellow water-soluble copolymer, i.e., poly((Z)-2-(2-(2-(4-(2-cyano-2-(3,4,5-tri(dodecyloxy)phenyl)vinyl)hydroxyethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethyl methacrylate-polyethylene glycol methyl ether methacrylate); Step S100, dissolving 1 g of the water-soluble copolymer prepared in step S90 in 1 mL of ultrapure water, ultrasonicating until the solution is clear, then moving the solution to 365 nm ultraviolet light and irradiating it at room temperature for 12 h, and freeze-drying and separation to obtain viscous yellow solid fluorescent single-chain polymer nanoparticles, whose chemical formula has x=0.67, y=0.33.

[0045] Example 5 Step S90, 0.2 g of polyethylene glycol methyl ether methacrylate, 0.12 g of (Z)-2-(2-(2-(2-(4-(2-cyano-2-(3,4,5-tri(dodecyloxy)phenyl)vinyl)hydroxyethoxy)ethoxy)ethoxy)ethoxy)ethyl methacrylate and 0.014 g of AIBN are dissolved in tetrahydrofuran solution, and the mixed solution is subjected to three freeze-vacuum-thaw cycles in a dry Schlenk tube in a nitrogen environment, and then stirred at 80° C. for 6 hours; after the reaction is completed, the mixture is separated and purified by column chromatography to obtain a viscous yellow water-soluble copolymer, i.e., poly((Z)-2-(2-(2-(4-(2-cyano-2-(3,4,5-tri(dodecyloxy)phenyl)vinyl)hydroxyethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethyl methacrylate-polyethylene glycol methyl ether methacrylate); Step S100, dissolving 1 g of the water-soluble copolymer prepared in step S90 in 1 mL of ultrapure water, ultrasonicating until the solution is clear, then moving the solution to 365 nm ultraviolet light and irradiating it at room temperature for 4 h, and freeze-drying and separating to obtain viscous yellow solid fluorescent single-chain polymer nanoparticles, whose chemical formula has x=0.86, y=0.14.

[0046] The above are only preferred embodiments of the present application, and are not intended to limit the patent scope of the present application. Any equivalent structure or equivalent process transformation made using the contents of the present application specification and drawings, or directly or indirectly applied in other related technical fields, are also included in the patent protection scope of the present application.

Claims

1. A fluorescent single-chain polymer nanoparticle, characterized in that: Its structural formula is: 。 2. A fluorescent single-chain polymer nanoparticle according to claim 1, characterized in that: In the structural formula, x+y=1.

3. A one-step preparation method of fluorescent single-chain polymer nanoparticles according to claim 1 or 2, characterized in that: include: Dissolving polyethylene glycol methyl ether methacrylate, cyanostilbene methacrylate monomer and an initiator in a ninth solvent to obtain a reaction solution, and subjecting the reaction solution to a polymerization reaction under a nitrogen environment to obtain poly((Z)-2-(2-(2-(2-(4-(2-cyano-2-(3,4,5-tri(dodecyloxy)phenyl)vinyl)hydroxyethoxy)ethoxy)ethoxy)ethoxy)ethyl methacrylate-polyethylene glycol methyl ether methacrylate); The poly((Z)-2-(2-(2-(2-(4-(2-cyano-2-(3,4,5-tri(dodecyloxy)phenyl)vinyl)hydroxyethoxy)ethoxy)ethoxy)ethoxy)ethyl methacrylate-polyethylene glycol methyl ether methacrylate) is dissolved in water to obtain a copolymer solution, the copolymer solution is irradiated under an ultraviolet lamp, and separated by freeze-drying to obtain fluorescent single-chain polymer nanoparticles.

4. The "one-step" preparation method of fluorescent single-chain polymer nanoparticles according to claim 3, characterized in that: The preparation method of the cyano distilbene methacrylate monomer comprises: Dissolving 3,4,5-trihydroxybenzaldehyde, 1-bromododecane, tetrabutylammonium iodide and potassium carbonate in a first solvent, and performing a first substitution reaction to obtain 3,4,5-tri(dodecyloxy)benzaldehyde; Dissolving 3,4,5-tri(dodecyloxy)benzaldehyde in a second solvent to obtain a 3,4,5-tri(dodecyloxy)benzaldehyde solution, dropping a lithium aluminum hydride solution into the 3,4,5-tri(dodecyloxy)benzaldehyde solution, and performing a reduction reaction to obtain 3,4,5-tri(dodecyloxy)benzyl alcohol; Dissolving 3, 4, 5-tri(dodecyloxy)benzyl alcohol in a third solvent to obtain a 3, 4, 5-tri(dodecyloxy)benzyl alcohol solution, adding a phosphorus tribromide solution dropwise to the 3, 4, 5-tri(dodecyloxy)benzyl alcohol solution, and performing a second substitution reaction to obtain 5-(bromomethyl)-1,2,3-tri(dodecyloxy)benzene; The 5-(bromomethyl)-1,2,3-tri(dodecyloxy)benzene, trimethylsilyl cyanide and tetrabutylammonium fluoride are dissolved in a fourth solvent and subjected to a first nucleophilic substitution reaction to obtain 3,4,5-tri(dodecyloxy)benzeneacetonitrile; dissolving tetraethylene glycol and triethylamine in a fifth solvent to obtain a first mixed solution, dropping a 4-toluenesulfonyl chloride solution into the first mixed solution, and performing a second nucleophilic substitution reaction to obtain p-toluenesulfonate-tetraethylene glycol; Dissolving the p-toluenesulfonate-tetraethylene glycol, p-hydroxybenzaldehyde and carbonic acid in a sixth solvent, and performing a first nucleophilic addition reaction to obtain 4-(2-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)ethoxy)benzaldehyde; The 3,4,5-tri(dodecyloxy)benzylacetonitrile and the 4-(2-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)ethoxy)ethoxy)benzaldehyde are dissolved in a seventh solvent, and subjected to a second nucleophilic addition reaction and a dehydration reaction to obtain (Z)-3-(4-(2-(2-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)ethoxy)phenyl)-2-(3,4,5-tri(dodecyloxy)phenyl)acrylonitrile; The (Z)-3-(4-(2-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)ethoxy)phenyl)-2-(3,4,5-tri(dodecyloxy)phenyl)acrylonitrile and triethylamine are dissolved in an eighth solvent to obtain a second mixed solution, the methacrylic chloride solution is added dropwise to the second mixed solution, and a third nucleophilic substitution reaction is performed to obtain a cyano distilbene methacrylate monomer.

5. The "one-step" preparation method of fluorescent single-chain polymer nanoparticles according to claim 4, characterized in that: In the first substitution reaction, the molar ratio of 3,4,5-trihydroxybenzaldehyde, 1-bromododecane, tetrabutylammonium iodide and potassium carbonate is 1:3:0.1:(3-1):5:0.2:8, the reaction temperature is 80-85°C, and the reaction time is 12-24h; In the reduction reaction, the molar ratio of the 3,4,5-tri(dodecyloxy)benzaldehyde to the lithium aluminum hydride in the lithium aluminum hydride solution is 1:1-2, the dropping temperature is -5-5°C, and the reaction conditions are: react at -5-5°C for 0.5-1h and then react at 20-30°C for 2-3h; In the second substitution reaction, the molar ratio of the 3, 4, 5-tri(dodecyloxy)benzyl alcohol to the phosphorus tribromide in the phosphorus tribromide solution is 1:1-2, the dropping temperature is -5-5°C, the reaction temperature is 20-30°C, and the reaction time is 3-4h; In the first nucleophilic substitution reaction, the molar ratio of 5-(bromomethyl)-1,2,3-tri(dodecyloxy)benzene, trimethylsilyl cyanide and tetrabutylammonium fluoride is 1:1.2:(0.2~1):1.5:1.5, the reaction temperature is 20~30°C, and the reaction time is 3~4h.

6. The "one-step" preparation method of fluorescent single-chain polymer nanoparticles according to claim 4, characterized in that: In the second nucleophilic substitution reaction, the molar ratio of 4-toluenesulfonyl chloride, tetraethylene glycol and triethylamine in the reaction solution is 1:1:(1.1-4):1:1.2, the dropping temperature is -5-5°C, the reaction temperature is 20-30°C, and the reaction time is 0.5-1h; In the first nucleophilic addition reaction, the molar ratio of the p-toluenesulfonate-tetraethylene glycol, p-hydroxybenzaldehyde and carbonic acid is 1:1:(2-1.1):1:3, the reaction temperature is 80-85°C, and the reaction time is 12-24h; In the second nucleophilic addition reaction, the molar ratio of the 3,4,5-tri(dodecyloxy)benzylacetonitrile to the 4-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)ethoxy)benzaldehyde is 1-1.2:1, the reaction temperature is 40-50° C., and the reaction time is 12-24 h; In the third nucleophilic substitution reaction, the molar ratio of the (Z)-3-(4-(2-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)ethoxy)phenyl)-2-(3,4,5-tri(dodecyloxy)phenyl)acrylonitrile, the triethylamine and the methacrylic chloride solution is 1:1:(1.5~1):3:3, the dropping temperature is -5~5°C, the reaction temperature is 20~30°C, and the reaction time is 12~24h.

7. The "one-step" preparation method of fluorescent single-chain polymer nanoparticles according to claim 4, characterized in that: The first solvent is N,N-dimethylformamide solution, the second solvent is tetrahydrofuran solution, the third solvent is dichloromethane solution, and the fourth solvent is acetonitrile; The fifth solvent is a dichloromethane solution, the sixth solvent is an N,N-dimethylformamide solution, the seventh solvent is a mixed solution of ethanol and tetrabutylammonium hydroxide, the volume ratio of the ethanol to the tetrabutylammonium hydroxide is 20-30:1, and the eighth solvent is a dichloromethane solution.

8. The "one-step" preparation method of fluorescent single-chain polymer nanoparticles according to claim 3, characterized in that: Before the polymerization reaction, the reaction solution is subjected to a freeze-vacuum-thaw cycle in a nitrogen environment; and after the polymerization reaction, the reaction product is separated and purified.

9. The "one-step" preparation method of fluorescent single-chain polymer nanoparticles according to claim 3, characterized in that: The reaction temperature of the polymerization reaction is 73-76° C., and the reaction time is 10-12 h. The ninth solvent is a tetrahydrofuran solution. The wavelength of the ultraviolet lamp is 365 nm, and the irradiation time is 6-12 h.

10. Use of the fluorescent single-chain polymer nanoparticles according to claim 1 or 2 in catalysts, biosensors, nanoreactors or nanomedicines.

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