Organic compound, amphiphilic polymer and application thereof

Abstract

The invention relates to the technical field of luminescent materials, and discloses an organic compound, an amphiphilic polymer and application thereof, and the organic compound has a structure as shown in a formula (I). The organic compound and the amphiphilic polymer provided by the invention have dual fluorescence emission, and can be used for amphiphilic aggregation-induced emission (AIE) polymer fluorescent materials. # imgabs0 #

Description

Technical Field

[0001] The invention relates to the technical field of luminescent materials, in particular to organic compounds and amphiphilic polymers and applications thereof. Background Art

[0002] Since the discovery of fluorescence, after decades of development, the demand for luminescent materials in various fields has continued to expand, especially fluorescent materials with aggregation-induced emission effect, which emit strong fluorescence in the aggregated state. Using fluorescent signals for visual sensing is a powerful chemical and physical detection method, making it widely used in fields such as bio-imaging and bio-imaging.

[0003] However, with the development of science and technology, the requirements for detection accuracy in the biological field are getting higher and higher. At present, most fluorescent sensors work by responding to changes in a single emission signal. In the actual sensing process, fluctuations in probe concentration or fluid properties can easily lead to signal reading errors, and the current calibration method cannot eliminate the influence of background autofluorescence overlap. The development of fluorescent materials with single chromophore dual fluorescence emission is expected to solve this problem.

[0004] Exploring unique photoluminescence technology has become the research focus of fluorescent materials. Summary of the invention

[0005] The purpose of the present invention is to develop a series of novel amphiphilic aggregation-induced luminescent fluorescent polymers capable of emitting two wavelengths, and to obtain fluorescent emission of multiple colors by controlling the ratio of polymer monomers and adjusting the ratio of two emission peaks.

[0006] In order to achieve the above purpose, the present invention first uses 4,4'-difluorodiphenyl sulfone as an electron acceptor (A), 5-aminoindole and one of its derivatives as an electron donor (D), phenothiazine or phenoxazine or carbazole or 9,9-dimethylacridine or one of 9,9-diphenylacridine and its derivatives as an electron donor (D') at the other end to synthesize an asymmetric fluorescent compound with alternating donors and acceptors (DAD'). The interaction between two different donors and acceptors enables the compound to have dual fluorescence emission, and the compound is a hydrophobic fluorescent material that produces dual fluorescence emission from a single chromophore.

[0007] Specifically, the present invention provides an organic compound having a structure shown in formula (I):

[0008]

[0009] Wherein, in formula (I),

[0010] L is present or absent, and the optional L is a linking group formed by benzene leaving any two H capable of leaving;

[0011] R 11 , R 12 , R 13 , R 31 , R 32 , R 33 , R 34 , R 41 , R 42 , R 43 and R 44 Each independently selected from H, C 1-6 Alkyl, C 1-6 Alkoxyl groups;

[0012] X is S, O or -C(R 51 R 52 )-,R 51 , R 52 Each independently selected from C 1-6 or X does not exist so that the two phenyl groups are directly bonded.

[0013] Furthermore, the present invention also connects with hydrophilic substances such as polyethylene glycol monomethyl ether methacrylate and its homologues, polyethylene glycol monomethyl ether acrylate and its homologues, 3,4,5-tri-(polyethylene glycol monomethyl ether) benzyl alcohol methacrylate and its homologues, 3,4,5-tri-(polyethylene glycol monomethyl ether) benzyl alcohol acrylate and its homologues through chemical bonds to construct a class of amphiphilic aggregation-induced luminescence polymer fluorescent materials with dual fluorescence emission. Specifically, the second aspect of the present invention provides an amphiphilic polymer, which contains an A structural unit and a B structural unit; the A structural unit is a structural unit provided by the organic compound described in the first aspect, and the B structural unit is a structural unit provided by the hydrophilic compound.

[0014] The third aspect of the present invention provides use of the organic compound described in the first aspect and the amphiphilic polymer described in the second aspect in aggregation-induced emission materials.

[0015] The fourth aspect of the present invention provides the use of the amphiphilic polymer described in the third aspect in an amphiphilic aggregation-induced emission polymer fluorescent material with dual fluorescence emission.

[0016] The present invention proposes an aggregation-induced luminescent material with dual fluorescence emission based on 4,4'-difluorodiphenyl sulfone units. By combining 4,4'-difluorodiphenyl sulfone (acceptor unit A) with one of 5-aminoindole and its derivatives (donor unit D) and phenothiazine or phenoxazine or carbazole or 9,9-dimethylacridine or one of 9,9-diphenylacridine and its derivatives (donor unit D'), a DAD' type fluorescent compound is constructed. The aggregation-induced luminescence property solves the influence of the aggregation luminescence quenching phenomenon of traditional fluorescent materials. In the sensor, the dual fluorescence emission can form two emission signals, which greatly reduces the reading error caused by environmental fluctuations and improves the detection accuracy. At the same time, by connecting with a hydrophilic compound through free radical polymerization, an amphiphilic polymer fluorescent material with dual fluorescence emission is constructed, so that it can be better applied to the fields of biological imaging, optical sensors, 3D movies and videos, data storage and probes. The luminescence properties of the obtained fluorescent materials are characterized by a fluorescence emission spectrometer, and the results show that these fluorescent materials all have dual fluorescence emission.

[0017] The organic compound and the amphiphilic polymer provided by the invention have dual fluorescence emission and can be used for amphiphilic aggregation-induced luminescence macromolecular fluorescent materials.

[0018] The material containing the amphiphilic polymer of the present invention can change its fluorescence color from yellow to blue by adjusting the ratio of hydrophilicity to hydrophobicity, and has good water solubility and biocompatibility, and can be used as a photoluminescent fluorescent material in the field of living biological imaging and smart materials. BRIEF DESCRIPTION OF THE DRAWINGS

[0019] Figure 1 This is the synthetic route for preparing the aggregation-induced emission (AIE) compound A1 with dual fluorescence emission in Example 1.

[0020] Figure 2 is the NMR spectrum of compound A1.

[0021] Figure 3 It is the fluorescence emission spectrum of compound A1 in tetrahydrofuran / water solution system.

[0022] Figure 4 This is a fluorescence photograph of a tetrahydrofuran-water solution of Compound A1 under 365nm ultraviolet light.

[0023] Figure 5 This is the synthetic route of the amphiphilic AIE random copolymer P1.

[0024] Figure 6 NMR spectra of amphiphilic AIE random copolymers P1 with different hydrophilic-hydrophobic ratios.

[0025] Figure 7GPC spectra of amphiphilic AIE random copolymer P1 with different hydrophilic-hydrophobic ratios.

[0026] Figure 8 Figure 2 Fluorescence emission spectra of amphiphilic AIE random copolymer P1 with different hydrophilic-hydrophobic ratios in tetrahydrofuran solution.

[0027] Fig. 9 Scanning electron microscopy image of nanoparticles prepared from amphiphilic AIE random copolymer P1.

[0028] Fig.10 This is the synthetic route of the hydrophilic dendritic monomer MA3EO.

[0029] Fig.11 This is a synthetic route for the amphiphilic dendritic fluorescent polymer P5 with dual fluorescence emission.

[0030] Fig.12 The NMR spectra of amphiphilic dendritic fluorescent polymer P5 with different hydrophilic-hydrophobic ratios.

[0031] Fig.13 The GPC spectra of amphiphilic dendritic fluorescent polymer P5 with different hydrophilic and hydrophobic ratios.

[0032] Fig.14 Figure 2 shows the fluorescence emission spectra of amphiphilic dendritic fluorescent polymer P5 with different hydrophilic-hydrophobic ratios in tetrahydrofuran solution.

[0033] Fig.15 Scanning electron microscopy image of nanoparticles prepared from amphiphilic dendritic fluorescent polymer P5. DETAILED DESCRIPTION

[0034] The endpoints and any values ​​of the ranges disclosed in this article are not limited to the precise ranges or values, and these ranges or values ​​should be understood to include values ​​close to these ranges or values. For numerical ranges, the endpoint values ​​of each range, the endpoint values ​​of each range and the individual point values, and the individual point values ​​can be combined with each other to obtain one or more new numerical ranges, which should be considered as specifically disclosed in this article.

[0035] “C 1-6 The term "alkyl" refers to an alkyl group having 1 to 6 carbon atoms, including straight-chain alkyl groups and branched-chain alkyl groups, for example, straight-chain alkyl groups and branched-chain alkyl groups having 1, 2, 3, 4, 5, or 6 carbon atoms, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, n-hexyl, etc.

[0036] “C 1-6The "alkoxy group" refers to an alkoxy group having a total of 1 to 6 carbon atoms, including straight-chain alkoxy groups and branched-chain alkoxy groups, for example, straight-chain alkoxy groups and branched-chain alkoxy groups having a total of 1, 2, 3, 4, 5, or 6 carbon atoms, for example, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, n-pentoxy, isopentyloxy, n-hexyloxy, and the like.

[0037] As mentioned above, the first aspect of the present invention provides an organic compound having a structure shown in formula (I);

[0038] Wherein, in formula (I),

[0039] L is present or absent, and the optional L is a linking group formed by benzene leaving any two H capable of leaving;

[0040] R 11 , R 12 , R 13 , R 31 , R 32 , R 33 , R 34 , R 41 , R 42 , R 43 and R 44 Each independently selected from H, C 1-6 Alkyl, C 1-6 Alkoxyl groups;

[0041] X is S, O or -C(R 51 R 52 )-,R 51 , R 52 Each independently selected from C 1-6 or X does not exist so that the two phenyl groups are directly bonded.

[0042] Preferably, in formula (I), L is present or absent, and the optional L is a linking group formed by benzene leaving any two H capable of leaving; R 11 , R 12 , R 13 , R 31 , R 32 , R 33 , R 34 , R 41 , R 42 , R 43 and R 44 Each independently selected from H, C 1-4 Alkyl, C 1-4 alkoxy; X is S, O or -C(R 51 R 52 )-,R51 , R 52 Each independently selected from C 1-6 or X does not exist so that the two phenyl groups are directly bonded.

[0043] Preferably, in formula (I), L is present or absent, and the optional L is a linking group formed by benzene leaving any two H capable of leaving; R 11 , R 12 , R 13 , R 31 , R 32 , R 33 , R 34 , R 41 , R 42 , R 43 and R 44 Each is independently selected from H, methyl, ethyl, n-propyl, isopropyl, methoxy, ethoxy, n-propoxy, isopropoxy, tert-butyl; X is S, O or -C(R 51 R 52 )-,R 51 , R 52 Each independently selected from C 1-6 or X does not exist so that the two phenyl groups are directly bonded.

[0044] According to a preferred embodiment, in formula (I), L is present or absent, and the optional L is 1,4-phenylene; R 11 , R 12 , R 13 , R 32 , R 33 , R 42 and R 43 Each is independently selected from H, methyl, ethyl, n-propyl, isopropyl, methoxy, ethoxy, n-propoxy, isopropoxy, tert-butyl;

[0045] R 31 , R 34 , R 41 and R 44 All are H;

[0046] X is S, O or -C(R 51 R 52 )-,R 51 , R 52 Each is independently selected from methyl, ethyl, n-propyl, isopropyl, tert-butyl, and phenyl; or X is absent so that the two phenyl groups are directly bonded.

[0047] According to a particularly preferred embodiment, the structure shown in formula (I) is selected from any one of the following:

[0048]

[0049]

[0050]

[0051] The organic matter provided by the present invention has dual fluorescence emission and can be used in aggregation-induced luminescence materials. For example, the electron acceptor in the organic matter of the present invention is 4,4'-difluorodiphenyl sulfone, one end of the electron donor is 5-aminoindole and one of its derivatives, and the other end is phenothiazine or phenoxazine or carbazole or 9,9-dimethylacridine or 9,9-diphenylacridine and one of its derivatives.

[0052] The organic matter provided by the invention has dual fluorescence emission.

[0053] The organic substances provided by the invention all exhibit aggregation-induced emission (AIE) characteristics.

[0054] The present invention has no particular limitation on the specific method for preparing the aforementioned organic matter. A person skilled in the art can obtain the aforementioned organic matter of the present invention according to the specific structural formula provided by the present invention in combination with the known knowledge in the field of synthesis. In addition, several examples are exemplarily listed in the following text of the present invention to illustrate the preparation method of the organic matter of the present invention. A person skilled in the art can also obtain the specific preparation method of all other organic matters by replacing the type of raw materials according to the preparation method of the organic matter in the following text of the present invention. The present invention will no longer describe in detail the preparation methods of all organic matters, and a person skilled in the art should not interpret this as a limitation of the present invention.

[0055] As mentioned above, the second aspect of the present invention provides an amphiphilic polymer, which contains an A structural unit and a B structural unit; the A structural unit is a structural unit provided by at least one of the organic compounds described in the first aspect, and the B structural unit is a structural unit provided by a hydrophilic compound.

[0056] Preferably, the hydrophilic compound is selected from at least one of polyethylene glycol monomethyl ether methacrylate and its homologues, polyethylene glycol monomethyl ether acrylate and its homologues, 3,4,5-tris-(polyethylene glycol monomethyl ether)benzyl alcohol methacrylate and its homologues, and 3,4,5-tris-(polyethylene glycol monomethyl ether)benzyl alcohol acrylate and its homologues.

[0057] Preferably, the molar ratio of the A structural unit to the B structural unit is 1:0.001-1000.

[0058] Preferably, the weight average molecular weight of the amphiphilic polymer is 600 to 500,000.

[0059] According to a particularly preferred embodiment, the amphiphilic polymer is selected from any one of the following, and each x, each y, and each n are each independently selected from a positive integer of 1-1000, more preferably each x, each y, and each n are each independently selected from a positive integer of 1-200:

[0060]

[0061]

[0062]

[0063]

[0064] The amphiphilic aggregation-induced luminescent fluorescent polymer capable of emitting two wavelengths provided by the present invention can obtain fluorescent emission of multiple colors by controlling the ratio of polymer monomers and adjusting the ratio of two emission peaks. It can be used in the fields of biological imaging, optical sensors, 3D movies and videos, data storage, and probes.

[0065] The present invention has no particular limitation on the specific method for preparing the aforementioned amphiphilic polymers. Those skilled in the art can obtain the aforementioned amphiphilic polymers of the present invention according to the structural formula in combination with known knowledge in the field of synthesis (or polymerization). In addition, several examples are exemplarily listed in the following text of the present invention to illustrate the preparation method of the amphiphilic polymers of the present invention. Those skilled in the art can also obtain the specific preparation method of all other amphiphilic polymers by replacing the types of raw materials according to the preparation method of the amphiphilic polymers in the following text of the present invention. The present invention no longer describes in detail the preparation methods of all amphiphilic polymers, which should not be understood by those skilled in the art as limiting the present invention.

[0066] As mentioned above, the third aspect of the present invention provides the use of the organic compound described in the first aspect and the amphiphilic polymer described in the second aspect in aggregation-induced emission materials.

[0067] As mentioned above, the fourth aspect of the present invention provides the use of the amphiphilic polymer described in the third aspect in an amphiphilic aggregation-induced emission polymer fluorescent material with dual fluorescence emission.

[0068] The present invention first uses 4,4'-difluorodiphenyl sulfone as an electron acceptor (A), 5-aminoindole and one of its derivatives as an electron donor (D), and phenothiazine or phenoxazine or carbazole or 9,9-dimethylacridine or 9,9-diphenylacridine and one of its derivatives as an electron donor (D') at the other end to synthesize an asymmetric donor and acceptor alternating (DAD') fluorescent material with aggregation-induced luminescence properties. The interaction of two different donor-acceptors enables it to have dual fluorescence emission, and then it is connected with a hydrophilic compound through a chemical bond to construct a class of amphiphilic aggregation-induced luminescence polymer fluorescent materials with dual fluorescence emission. The fluorescent material has good water solubility and dual fluorescence emission characteristics. Because its fluorescence color change range is wider and the fluorescence color is adjustable, it can be used as a photoluminescent polymer material in the fields of biological imaging, light sensors, 3D movies and videos, data storage, and probes.

[0069] The drugs and reagents used in the following specific examples are all of analytical purity and, unless otherwise specified, can be obtained from commercial sources and used directly without purification.

[0070] Example 1

[0071] This example proposes an AIE compound A1 with dual fluorescence emission, which uses 4,4'-difluorodiphenyl sulfone as an electron acceptor (A), phenothiazine as an electron donor (D), and N-(1H-indole)-5-methylacrylamide as an electron donor at the other end (D').

[0072] Combination Figure 1 This embodiment is further described, and its synthetic route comprises the following steps:

[0073] Step 1: Add 0.1mol sodium hydride and 0.05mol phenothiazine to a 500ml three-necked flask in turn, then add 100mL dry DMF and stir at room temperature for 30min. Then add 200mL of DMF solution containing 0.05mol of 4,4'-difluorodiphenyl sulfone, and stir the reaction at 130°C for 2h under a nitrogen atmosphere. After the reaction is completed, pour the mixture into 1000mL of water, and the product precipitates. Filter, wash the filter cake with water, and dry to obtain a crude product. The crude product is separated and purified by column chromatography using dichloromethane / petroleum ether (volume ratio 4:1) as the eluent, and the collected solution is spin-dried and dried for 24h to obtain a light yellow solid with a yield of 45.3%. The light yellow solid was characterized, and the results were: 1 H NMR (δ, ppm, DMSO-d 6):8.01-7.93(m,2H),7.86-7.78(m,2H),7.58-7.51(m,2H),7.49-7.35(m,6H),7.34-7.24(m,2H),7.13-7.05(m,2H).

[0074] Step 2: Add 0.02 mol of 10-(4-((4-fluorophenyl)sulfonyl)phenyl)-10H-phenothiazine, 0.02 mol of 5-nitroindole, and 0.2 mol of potassium carbonate to a 150 mL round-bottom flask. Add 60 mL of dry N-methylpyrrolidone (NMP) and stir at 140 ° C for 8 hours. After cooling, pour the mixture into 1000 mL of water, and the product precipitates. Filter, wash with water and petroleum ether, and dry to obtain a crude product 1. Dissolve 0.2 mol of the dried crude product 1 in 1000 mL of anhydrous ethanol, stir evenly, and add 0.2 mol of SnCl 2 ·2H 2 O. The reaction mixture was heated to reflux for 24 h, and TLC was followed until the reaction was complete. The reaction mixture was cooled and poured into 2500 mL of ice water, and then adjusted to pH = 7 with an aqueous NaOH solution, extracted with dichloromethane, and the extract was dried over anhydrous magnesium sulfate. Filtered and desolventized to obtain a crude product 2. Subsequently, column chromatography was performed using dichloromethane / petroleum ether (volume ratio 4:1) as an eluent, and the collected solution was spin-dried and dried for 24 h to obtain a yellow solid with a yield of 68.7%. The yellow solid was characterized, and the results were: 1 HNMR (δ, ppm, DMSO-d 6 ):8.05-7.97(m,2H),7.91-7.83(m,2H),7.80-7.73(m,2H),7.60-7.51(m,3H),7.46-7.37(m,5H),7.29(ddd,J=7.7,5.8, 2.9Hz,2H),7.17-7.10(m,2H),6.78-6.74(m,1H),6.59(dd,J=8.7,2.2Hz,1H),6.49(dd,J=3.4,0.8Hz,1H),4.77(s,2H).

[0075] Step 3: Add 0.01 mol of 1-(4-((4-(10H-phenothiazine)-10-phenyl)sulfonyl)phenyl)-1H-indole-5-amine, 5 mL of triethylamine and 50 mL of dry dichloromethane to a 150 mL three-necked flask, stir, and place in an ice bath to cool to 5-10°C. Slowly drop 0.03 mol of methacryloyl chloride, remove the ice bath after the drop, react at room temperature for 4 hours, and track the reaction by TLC until the reaction is complete. Pour the reaction solution into 200 mL of ice water, add 100 mL of dichloromethane to extract the product, remove the excess methacryloyl chloride with a saturated sodium bicarbonate solution, and dry in anhydrous magnesium sulfate for 12 hours. Filter and spin dry to obtain a crude product. The crude product is separated and purified by column chromatography using dichloromethane / ethyl acetate (volume ratio 10:1) as an eluent, and the collected solution is spin dried and dried for 24 hours to obtain an orange-yellow solid final product A1 with a yield of 63.2%. The orange-yellow solid was characterized and the results were: 1 H NMR (δ, ppm, DMSO-d 6 ):9.77(s,1H),8.10-8.02(m,3H),7.92-7.81(m,4H),7.73(d,J=3.4Hz,1H),7.64(d,J=8.9Hz,1H),7.56(dt,J=7.7,1.0Hz,2H),7.49- 7.38(m,5H),7.34-7.27(m,2H),7.14-7.09(m,2H),6.76-6.71(m,1H),5.82(t,J=1.1Hz,1H),5.53-5.46(m,1H),1.97(d,J=1.3Hz,3H).

[0076] Figure 2 is the NMR spectrum of compound A1.

[0077] Figure 3 The fluorescence emission spectrum of compound A1 in tetrahydrofuran-water system. Wherein, (a) represents the fluorescence emission spectrum of compound A1 in tetrahydrofuran-water system with different water contents (0-70%); (b) represents the fluorescence emission spectrum of compound A1 in tetrahydrofuran-water system with different water contents (70-95%). As can be seen from the figure, when the water content gradually increases from 0%, the fluorescence emission shifts to red light and gradually weakens. This is because there is a strong π-π non-covalent bond interaction between the benzene ring in compound A1, and the red shift is attributed to the strong polarity of water. The disappearance of emission peak 3 is consistent with the solvation effect described above; when the water content increases from 50% to 95%, the three emissions shift to blue light and gradually increase. This is because water forms hydrogen bonds with compound A1, which greatly changes the fluorescence emission and causes blue shift. When the water content reaches 95%, its fluorescence intensity is 17 times that of pure tetrahydrofuran, indicating that it has typical AIE properties.

[0078] Figure 4 This is a fluorescence photograph of a tetrahydrofuran-water solution of compound A1 under 365nm ultraviolet light. From the figure, we can see that the solution light changes from orange to yellow, and the fluorescence intensity decreases first and then increases, indicating that it has typical AIE properties, and the mechanism of the AIE phenomenon is hindered intramolecular rotation (RIR).

[0079] Example 2

[0080] Combination Figure 5 This embodiment is further described, and its synthetic route comprises the following steps:

[0081] This embodiment proposes to use AIE compound A1 with dual fluorescence emission as the hydrophobic segment and polyethylene glycol monomethyl ether methacrylate as the hydrophilic segment, and to prepare 5 different proportions of amphiphilic AIE random copolymers P1 with dual fluorescence emission (wherein n in polyethylene glycol monomethyl ether methacrylate is 8) by free radical polymerization.

[0082] Synthesis method: Take a clean and dry glass test tube, add magnetite, add 0.4mmol fluorescent monomer compound A1, 2mmol polyethylene glycol monomethyl ether methacrylate, 267μL of 0.01g / mL tetrahydrofuran solution of azobisisobutyronitrile (AIBN) (the molar ratio of monomer to initiator is 100:1), and 2.84g of refined tetrahydrofuran. Use a double-row tube to evacuate the reactant solution and replace it with nitrogen. Repeat three times. After the replacement is completed, heat and polymerize at 70℃ for 48h. After 48h, take out the test tube and quickly put it into liquid nitrogen to cool and stop the polymerization. Using anhydrous ether as a precipitant, the polymer was precipitated in anhydrous ether. The precipitation was repeated five times to obtain a yellow viscous liquid, which was placed in a vacuum drying oven and dried for 24 hours to obtain polymer P1 (the molar ratio of hydrophilic monomer: hydrophobic fluorescent monomer (that is, the molar ratio of y and x) was 5:1, 30:1, 50:1, 100:1, 200:1, respectively), with a yield of about 70%.

[0083] Figure 6 NMR spectra of amphiphilic AIE random copolymers P1 with different hydrophilic-hydrophobic ratios.

[0084] Figure 7 The GPC spectra of the amphiphilic AIE random copolymer P1 with different hydrophilic and hydrophobic ratios are shown in Figure 2. As can be seen from the figure, the molecular weights of the amphiphilic AIE random copolymer P1 are 6.68×10 4 g / mol, 10.43×10 4 g / mol, 7.31×10 4 g / mol, 7.98×10 4 g / mol and 7.24×10 4g / mol, and the molecular weight distributions are 1.65, 2.22, 2.04, 2.17 and 2.27, respectively.

[0085] Figure 8 Figure 2 is the fluorescence emission spectra of amphiphilic AIE random copolymer P1 with different hydrophilic and hydrophobic ratios in tetrahydrofuran solution. As can be seen from the figure, the amphiphilic AIE random copolymer P1 has dual fluorescence emission, which is 543nm yellow light (emission peak 2) and 430nm purple light (emission peak 1). At the same time, the emission wavelength and fluorescence intensity change with the change of the hydrophilic segment ratio. As the hydrophilic segment ratio increases, emission peak 1 gradually increases and emission peak 2 gradually decreases, causing it to gradually blue-shift from yellow light to purple light emission. This can be attributed to the introduction of the hydrophilic unit, which enhances the electron-donating ability of the donor unit, which is conducive to the generation of emission peak 1 fluorescence, resulting in an increase in the fluorescence intensity of emission peak 1 and a decrease in the fluorescence intensity of emission peak 2.

[0086] Fig. 9 The scanning electron microscope image of the nanoparticles prepared from the amphiphilic AIE random copolymer P1. The left side shows the TEM image of the amphiphilic AIE random copolymer P1 (the molar ratio of the hydrophilic monomer: the hydrophobic fluorescent monomer, that is, the molar ratio of y and x is 5:1); the right side shows the TEM image of the amphiphilic AIE random copolymer P1 (the molar ratio of the hydrophilic monomer: the hydrophobic fluorescent monomer, that is, the molar ratio of y and x is 100:1). It can be seen from the figure that when the fluorescent monomer: the hydrophilic monomer = 1:5, the structure of the polymer micelle is elliptical and the particle size distribution is moderate, which is consistent with the DLS test results; when the fluorescent monomer: the hydrophilic monomer = 1:100, because the hydrophilic segment is a linear structure, the structure of the polymer micelle is an irregular chain.

[0087] Example 3

[0088] Combination Fig.10 and Fig.11 This embodiment is further described, and its synthetic route comprises the following steps:

[0089] This example proposes using the AIE compound A1 with dual fluorescence emission as the hydrophobic segment and the hydrophilic dendron monomer MA3EO (synthetic route see Fig.10 , which is a known compound and the preparation method thereof will not be described in detail in the present invention) is a hydrophilic segment, and five amphiphilic dendritic polymers P5 with dual fluorescence emission in different proportions were prepared by free radical polymerization (wherein n in 3,4,5-tri-(polyethylene glycol monomethyl ether) benzyl alcohol methacrylate is 3).

[0090] Synthesis method: Take a clean, dry and well-drawn glass test tube, add magnetite, take 0.25g (0.4mmol) A1, 1.34g (2mmol) MA3EO, 267μl of 0.01g / ml AIBN tetrahydrofuran solution (the molar ratio of monomer to initiator is 100:1), 3.71g of refined tetrahydrofuran (solvent concentration is 70%). Use a double-row tube to evacuate the reactant solution and replace it with nitrogen, repeat three times, and after the replacement is completed, heat and polymerize at 70℃ for 48h. After 48h, take out the test tube and quickly put it into liquid nitrogen to cool and stop the polymerization. Using anhydrous ether as a precipitant, the polymer was precipitated in anhydrous ether. The precipitation was repeated 5 times to obtain a yellow viscous liquid, which was placed in a vacuum drying oven and dried for 24 hours to obtain 5 polymers (the molar ratio of hydrophilic monomer: hydrophobic fluorescent monomer (that is, the molar ratio of y to x) was 5:1, 10:1, 15:1, 20:1, 25:1, respectively), with a yield of about 73%.

[0091] Fig.12 The NMR spectra of the amphiphilic dendritic fluorescent polymer P5 with different hydrophilic and hydrophobic ratios are shown in the figure. As can be seen from the figure, due to the changes in the local charge density and magnetic field strength caused by polymerization, its chemical shift will gradually become wider; at the same time, as the proportion of the hydrophilic segment increases, the peak intensity of the proton hydrogen on the benzene ring gradually weakens, and the peak intensity of the proton hydrogen on the hydrophilic segment gradually increases, and the chemical shift of the carbon-carbon double bond at 5.83ppm and 5.51ppm disappears, indicating the successful synthesis of the target polymer P5, and the chemical shifts of the remaining hydrogens have been marked in the figure.

[0092] Fig.13 The GPC spectra of amphiphilic dendron fluorescent polymer P5 with different hydrophilic and hydrophobic ratios are shown in Figure 1. As can be seen from the figure, the molecular weights of amphiphilic dendron fluorescent polymer P5 are 6.84×10 4 g / mol, 6.99×10 4 g / mol, 7.62×10 4 g / mol, 5.98×10 4 g / mol and 5.83×10 4 g / mol, and its molecular weight distribution is less than 2.

[0093] Fig.14 The fluorescence emission spectra of the amphiphilic dendritic fluorescent polymer P5 with different hydrophilic and hydrophobic ratios in tetrahydrofuran / petroleum ether system are shown in the figure. As can be seen from the figure, with the increase of the hydrophilic unit ratio, the emission peak 1 gradually increases and the emission peak 2 gradually decreases. This can be attributed to the introduction of the hydrophilic unit, which enhances the electron-donating ability of the indole end and is conducive to the generation of fluorescence; the donor-acceptor interaction at the other end is weakened, and the fluorescence intensity gradually decreases.

[0094] Fig.15The scanning electron microscope image of the nanoparticles prepared by the amphiphilic dendron fluorescent polymer P5. The left side shows the TEM image of the amphiphilic dendron fluorescent polymer P5 (the molar ratio of hydrophilic monomer: hydrophobic fluorescent monomer, that is, the molar ratio of y and x is 10:1) at 25°C; the right side shows the TEM image of the amphiphilic AIE random copolymer P1 (the molar ratio of hydrophilic monomer: hydrophobic fluorescent monomer, that is, the molar ratio of y and x is 5:1) at 60°C: It can be seen from the figure that when the fluorescent monomer: hydrophilic monomer = 1:10, the morphology of the polymer micelles is still elliptical. When the temperature exceeds the LCST, the polymer micelles aggregate, the morphology gradually becomes round, and the particle size increases.

[0095] Example 4

[0096] This example proposes an AIE compound A16 with dual fluorescence emission, which uses 4,4'-difluorodiphenyl sulfone as an electron acceptor (A), 2-methoxyphenothiazine as an electron donor (D), and N-(1H-indole)-5-methylacrylamide as an electron donor at the other end (D').

[0097] The synthesis steps are similar to those in Example 1. Figure 1 This embodiment is further described, and its synthetic route comprises the following steps:

[0098] Step 1: Add 0.1mol sodium hydride and 0.05mol 2-methoxyphenothiazine to a 500ml three-necked flask in turn, then add 100mL dry DMF and stir at room temperature for 30min. Then add 200mL DMF solution containing 0.05mol 4,4'-difluorodiphenyl sulfone, stir and react at 130℃ for 2h under nitrogen atmosphere. After the reaction is completed, pour the mixture into 1000mL water, and the product precipitates. Filter, wash the filter cake with water, and dry to obtain a crude product. The crude product is separated and purified by column chromatography using dichloromethane / petroleum ether (volume ratio 6:1) as eluent, and the collected solution is spin-dried and dried for 24h to obtain a light yellow solid with a yield of 55.6%. The light yellow solid was characterized, and the results were: 1 H NMR (δ, ppm, DMSO-d 6 ):8.01-7.93(m,2H),7.86-7.78(m,2H),7.58-7.51(m,2H),7.49-7.35(m,6H),7.34-7.24(m,2H),7.13-7.05(m,2H),3.84-3.64(m,3H).

[0099] Step 2: Add 0.02 mol of 10-(4-((4-fluorophenyl)sulfonyl)phenyl)-3-methoxyphenothiazine, 0.02 mol of 5-nitroindole, and 0.2 mol of potassium carbonate to a 150 mL round-bottom flask. Add 60 mL of dry N-methylpyrrolidone (NMP) and stir at 140 ° C for 8 h. After cooling, pour the mixture into 1000 mL of water, and the product precipitates. Filter, wash with water and petroleum ether, and dry to obtain a crude product 1. Dissolve 0.2 mol of the dried crude product 1 in 1000 mL of anhydrous ethanol, stir evenly, and add 0.2 mol of SnCl 2 ·2H 2 O. The reaction mixture was heated to reflux for 24 h, and TLC was followed until the reaction was complete. The reaction mixture was cooled and poured into 2500 mL of ice water, and then adjusted to pH = 7 with an aqueous NaOH solution, extracted with dichloromethane, and the extract was dried over anhydrous magnesium sulfate. Filtered and desolventized to obtain a crude product 2. Subsequently, column chromatography was performed using dichloromethane / petroleum ether (volume ratio 5:1) as an eluent, and the collected solution was spin-dried and dried for 24 h to obtain a yellow solid with a yield of 72.5%. The yellow solid was characterized, and the results were: 1 H NMR (δ, ppm, DMSO-d 6 ):8.05-7.97(m,2H),7.91-7.83(m,2H),7.80-7.73(m,2H),7.60-7.51(m,3H),7.46-7.37(m,5H),7.29(ddd,J=7.7,5.8,2.9Hz,2H ),7.17-7.10(m,2H),6.78-6.74(m,1H),6.59(dd,J=8.7,2.2Hz,1H),6.49(dd,J=3.4,0.8Hz,1H),4.77(s,2H),3.84-3.64(m,3H).

[0100] Step 3: Add 0.01 mol of 1-(4-((4-(3-methoxyphenothiazine)-10-phenyl)sulfonyl)phenyl)-1H-indole-5-amine, 5 mL of triethylamine and 50 mL of dry dichloromethane to a 150 mL three-necked flask, stir, and place in an ice bath to cool to 5-10°C. Slowly drop 0.03 mol of methacryloyl chloride, remove the ice bath after the drop, react at room temperature for 4 hours, and track the reaction by TLC until the reaction is complete. Pour the reaction solution into 200 mL of ice water, add 100 mL of dichloromethane to extract the product, remove the excess methacryloyl chloride with a saturated sodium bicarbonate solution, and dry in anhydrous magnesium sulfate for 12 hours. Filter and spin dry to obtain a crude product. The crude product is separated and purified by column chromatography using dichloromethane / ethyl acetate (volume ratio 8:1) as an eluent, and the collected solution is spin dried and dried for 24 hours to obtain an orange-yellow solid final product A16 with a yield of 58.2%. The orange-yellow solid was characterized and the results were: 1 HNMR (δ, ppm, DMSO-d 6 ):9.77(s,1H),8.10-8.02(m,3H),7.92-7.81(m,4H),7.73(d,J=3.4Hz, 1H),7.64(d,J=8.9Hz,1H),7.56(dt,J=7.7,1.0Hz,2H),7.49-7.38(m,5 H),7.34-7.27(m,2H),7.14–7.09(m,2H),6.76-6.71(m,1H),5.82(t,J= 1.1Hz, 1H), 5.53-5.46 (m, 1H), 1.97 (d, J = 1.3Hz, 3H), 3.84-3.64 (m, 3H).

[0101] Example 5

[0102] The synthesis method is similar to that of Example 2, Figure 5 This embodiment is further described, and its synthetic route comprises the following steps:

[0103] This embodiment proposes to use AIE compound A16 with dual fluorescence emission as the hydrophobic segment and polyethylene glycol monomethyl ether methacrylate as the hydrophilic segment, and to prepare 5 different proportions of amphiphilic AIE random copolymers P13 with dual fluorescence emission (wherein n in polyethylene glycol monomethyl ether methacrylate is 8) by free radical polymerization.

[0104] Synthesis method: Take a clean and dry glass test tube, add magnetite, add 0.4mmol fluorescent monomer compound A16, 2mmol polyethylene glycol monomethyl ether methacrylate, 267μL of 0.01g / mL tetrahydrofuran solution of azobisisobutyronitrile (AIBN) (the molar ratio of monomer to initiator is 100:1), and 2.84g of refined tetrahydrofuran. Use a double-row tube to evacuate the reactant solution and replace it with nitrogen. Repeat three times. After the replacement is completed, heat and polymerize at 70℃ for 48h. After 48h, take out the test tube and quickly put it into liquid nitrogen to cool and stop the polymerization. The polymer was precipitated in anhydrous ether using anhydrous ether as a precipitant. The precipitation was repeated five times to obtain a yellow viscous liquid, which was then dried in a vacuum drying oven for 24 hours to obtain polymer P13 (the molar ratio of hydrophilic monomer: hydrophobic fluorescent monomer (i.e., the molar ratio of y to x) was 8:1, 16:1, 32:1, 64:1, 128:1, respectively) with a yield of 75%.

[0105] Example 6

[0106] The synthesis method is similar to that in Example 3, Fig.11 This embodiment is further described, and its synthetic route comprises the following steps:

[0107] This embodiment proposes to use AIE compound A16 with dual fluorescence emission as the hydrophobic segment and hydrophilic dendron monomer MA3EO as the hydrophilic segment, and to prepare 5 different proportions of amphiphilic dendron polymers P17 with dual fluorescence emission (wherein n of 3,4,5-tri-(polyethylene glycol monomethyl ether) benzyl alcohol methacrylate is 3) by free radical polymerization.

[0108] Synthesis method: Take a clean, dry and well-drawn glass test tube, add magnetite, take 0.25g (0.4mmol) A16, 1.34g (2mmol) MA3EO, 267μl 0.01g / ml AIBN tetrahydrofuran solution (the molar ratio of monomer to initiator is 100:1), 3.71g refined tetrahydrofuran (solvent concentration is 70%). Use a double-row tube to evacuate the reactant solution and replace it with nitrogen, repeat three times, and after the replacement is completed, heat and polymerize at 70℃ for 48h. After 48h, take out the test tube and quickly put it into liquid nitrogen to cool and stop the polymerization. Using anhydrous ether as a precipitant, the polymer was precipitated in anhydrous ether. The precipitation was repeated 5 times to obtain a yellow viscous liquid, which was placed in a vacuum drying oven and dried for 24 hours to obtain 5 polymers (the molar ratio of hydrophilic monomer: hydrophobic fluorescent monomer (that is, the molar ratio of y to x) was 5:1, 10:1, 15:1, 20:1, 25:1, respectively), with a yield of 78%.

[0109] Example 7

[0110] This embodiment proposes an AIE compound with dual fluorescence emission using 4,4'-difluorodiphenyl sulfone as an electron acceptor (A), 3,6-di-tert-butylcarbazole as an electron donor (D), and N-(1H-indole)-5-methylacrylamide as an electron donor at the other end (D').

[0111] The synthesis steps are similar to those in Example 1. Figure 1 This embodiment is further described, and its synthetic route comprises the following steps:

[0112] Synthesis method of A28:

[0113] Step 1: Add 4,4'-difluorodiphenyl sulfone (8.32g, 20mmol), 3,6-di-tert-butylcarbazole (3.97g, 11mmol), cuprous iodide (4.52g, 23.75mmol), potassium carbonate (6.84g, 49.48mmol), 1,10-phenanthroline (0.53g, 2.97mmol) into a 500ml three-necked flask, and add 200ml of dry N,N-dimethylformamide. Expel the air in the three-necked flask with nitrogen gas, and carry out the reaction in a nitrogen atmosphere. Stir at room temperature for 30min and then heat to 120℃ for reaction. TCL spot plate tracking, 3,6-di-tert-butylcarbazole reacts completely, the reaction time is 48h, after the reaction is completed, add water to quench the reaction and then filter, wash the filter cake with water several times and then dry the filter cake. The dried solid was dissolved in dichloromethane and then filtered, and the filtrate was purified by chromatography column method (the volume ratio of dichloromethane to ethyl acetate was 25:1, and the target product was collected by column chromatography), the solvent was dried by spin drying, and the spin dried solid was placed in a vacuum drying oven at 40°C and dried under vacuum, with a yield of 70.2%. The product was characterized, and the results were as follows: 1 HNMR (δ, ppm, DMSO-d 6 ):8.01-7.93(m,2H),7.86-7.78(m,2H),7.58-7.51(m,2H),7.49-7.35(m,6H),7.34-7.24(m,2H),7.13-7.05(m,2H).1.42-1.45(m,18H).

[0114] Step 2: Add 0.02 mol of the product of step 1, 0.02 mol of 5-nitroindole, and 0.2 mol of potassium carbonate into a 150 mL round-bottom flask. Add 60 mL of dry N-methylpyrrolidone (NMP) and stir at 140 ° C for 8 hours. After cooling, pour the mixture into 1000 mL of water, and the product precipitates. Filter, wash with water and petroleum ether, and dry to obtain the crude product 1. Dissolve 0.2 mol of the dried crude product 1 in 1000 mL of anhydrous ethanol, stir evenly, and add 0.2 mol of SnCl 2 ·2H 2O. The reaction mixture was heated to reflux for 24h and followed by TLC until the reaction was complete. The reaction mixture was cooled and poured into 2500mL of ice water, then adjusted to pH=7 with aqueous NaOH solution, extracted with dichloromethane, and the extract was dried over anhydrous magnesium sulfate. Filtered and desolventized to obtain the crude product 2. Subsequently, column chromatography was performed using dichloromethane / petroleum ether (volume ratio 6:1) as the eluent, and the collected solution was spin-dried and dried for 24h to obtain a yellow solid with a yield of 78.2%. The product was characterized, and the results were as follows: 1 HNMR (δ, ppm, DMSO-d 6 ):8.05-7.97(m,2H),7.91-7.83(m,2H),7.80-7.73(m,2H),7.60-7.51(m,3H),7.46-7.37(m,5H),7.29(ddd,J=7.7,5.8,2.9Hz,2H ),7.17-7.10(m,2H),6.78-6.74(m,1H),6.59(dd,J=8.7,2.2Hz,1H),6.49(dd,J=3.4,0.8Hz,1H),4.77(s,2H),1.42-1.45(m,18H).

[0115] Step 3: Add 0.01 mol of the product of step 2, 5 mL of triethylamine and 50 mL of dry dichloromethane to a 150 mL three-necked flask, stir, and place in an ice bath to cool to 5-10 ° C. Slowly drop 0.03 mol of methacryloyl chloride, remove the ice bath after the drop, react at room temperature for 4 hours, and track the reaction by TLC until the reaction is complete. Pour the reaction solution into 200 mL of ice water, add 100 mL of dichloromethane to extract the product, remove the excess methacryloyl chloride with saturated sodium bicarbonate solution, and dry in anhydrous magnesium sulfate for 12 hours. Filter and spin dry to obtain a crude product. The crude product is separated and purified by column chromatography using dichloromethane / ethyl acetate (volume ratio 14:1) as the eluent, and the collected solution is spin-dried and dried for 24 hours to obtain an orange-yellow solid final product A28 with a yield of 58.2%. The product was characterized, and the results were: 1 H NMR (δ, ppm, DMSO-d 6):9.77(s,1H),8.10-8.02(m,3H),7.92-7.81(m,4H),7.73(d,J=3.4Hz, 1H),7.64(d,J=8.9Hz,1H),7.56(dt,J=7.7,1.0Hz,2H),7.49-7.38(m,5H ),7.34-7.27(m,2H),7.14–7.09(m,2H),6.76-6.71(m,1H),5.82(t,J=1 .1Hz,1H),5.53-5.46(m,1H),1.97(d,J=1.3Hz,3H),1.42-1.45(m,18H).

[0116] Example 8

[0117] The synthesis method is similar to that of Example 2, Figure 5 This embodiment is further described, and its synthetic route comprises the following steps:

[0118] This embodiment proposes to use AIE compound A28 with dual fluorescence emission as the hydrophobic segment and polyethylene glycol monomethyl ether methacrylate as the hydrophilic segment, and to prepare 5 different proportions of amphiphilic AIE random copolymers P25 with dual fluorescence emission (wherein n in polyethylene glycol monomethyl ether methacrylate is 5) by free radical polymerization.

[0119] Synthesis method: Take a clean and dry glass test tube, add magnetite, add 0.4mmol fluorescent monomer compound A28, 2mmol polyethylene glycol monomethyl ether methacrylate, 267μL of 0.01g / mL tetrahydrofuran solution of azobisisobutyronitrile (AIBN) (the molar ratio of monomer to initiator is 100:1), and 2.84g of refined tetrahydrofuran. Use a double-row tube to evacuate the reactant solution and replace it with nitrogen. Repeat three times. After the replacement is completed, heat and polymerize at 70℃ for 48h. After 48h, take out the test tube and quickly put it into liquid nitrogen to cool and stop the polymerization. Using anhydrous ether as a precipitant, the polymer was precipitated in anhydrous ether. The precipitation was repeated five times to obtain a yellow viscous liquid, which was placed in a vacuum drying oven and dried for 24 hours to obtain polymer P25 (the molar ratio of hydrophilic monomer: hydrophobic fluorescent monomer (that is, the molar ratio of y to x) was 8:1, 16:1, 32:1, 64:1, 128:1, respectively), with a yield of 82%.

[0120] Example 9

[0121] The synthesis method is similar to that in Example 3, Fig.11 This embodiment is further described, and its synthetic route comprises the following steps:

[0122] This embodiment proposes to use AIE compound A28 with dual fluorescence emission as the hydrophobic segment and hydrophilic dendron monomer MA3EO as the hydrophilic segment, and to prepare 5 different proportions of amphiphilic dendron polymers P29 with dual fluorescence emission (wherein n of 3,4,5-tri-(polyethylene glycol monomethyl ether) benzyl alcohol methacrylate is 3) by free radical polymerization.

[0123] Synthesis method: Take a clean, dry and well-drawn glass test tube, add magnetite, take 0.25g (0.4mmol) A28, 1.34g (2mmol) MA3EO, 267μl of 0.01g / ml AIBN tetrahydrofuran solution (the molar ratio of monomer to initiator is 100:1), 3.71g of refined tetrahydrofuran (solvent concentration is 70%). Use a double-row tube to evacuate the reactant solution and replace it with nitrogen, repeat three times, and after the replacement is completed, heat and polymerize at 70°C for 48h. After 48h, take out the test tube and quickly put it into liquid nitrogen to cool and stop the polymerization. Using anhydrous ether as a precipitant, the polymer was precipitated in anhydrous ether. The precipitation was repeated 5 times to obtain a yellow viscous liquid, which was placed in a vacuum drying oven and dried for 24 hours to obtain 5 polymers (the molar ratio of hydrophilic monomer: hydrophobic fluorescent monomer (that is, the molar ratio of y to x) was 5:1, 10:1, 15:1, 20:1, 25:1, respectively), with a yield of 88%.

[0124] The compounds, copolymers and polymers of the present invention all have performance characterization results similar to those of the fluorescent compound A1 and / or the amphiphilic AIE random copolymer P1 and / or the amphiphilic dendritic polymer P5.

[0125] The above results indicate that the present invention provides a class of AIE fluorescent compounds with dual fluorescence emission. This class of material is a dual fluorescence emission material, which can effectively avoid the phenomenon that a single fluorescence signal is affected by environmental fluctuations, resulting in large errors in detection. At the same time, the amphiphilic AIE polymer with dual fluorescence emission formed after the introduction of hydrophilic compounds can be better applied in the fields of biological detection and biological imaging, and is an organic photoluminescent material with great application prospects.

[0126] The preferred embodiments of the present invention are described in detail above, but the present invention is not limited thereto. Within the technical concept of the present invention, the technical solution of the present invention can be subjected to a variety of simple modifications, including the combination of various technical features in any other suitable manner, and these simple modifications and combinations should also be regarded as the contents disclosed by the present invention and belong to the protection scope of the present invention.

Claims

1. An organic compound, characterized in that The organic compound has a structure shown in formula (I): Wherein, in formula (I), L is present or absent, and the optional L is a linking group formed by benzene leaving any two H capable of leaving; R 11 , R 12 , R 13 , R 31 , R 32 , R 33 , R 34 , R 41 , R 42 , R 43 and R 44 Each independently selected from H, C 1-6 Alkyl, C 1-6 Alkoxyl groups; X is S, O or -C(R 51 R 52 )-, R 51 , R 52 Each independently selected from C 1-6 or X does not exist so that the two phenyl groups are directly bonded.

2. The organic compound according to claim 1, characterized in that In formula (I), L may be present or absent, and the optional L is a linking group formed by benzene leaving any two H groups capable of leaving; R 11 , R 12 , R 13 , R 31 , R 32 , R 33 , R 34 , R 41 , R 42 , R 43 and R 44 Each independently selected from H, C 1-4 Alkyl, C 1-4 alkoxy; X is S, O or -C(R 51 R 52 )-,R 51 , R 52 Each independently selected from C 1-6 or X does not exist so that the two phenyl groups are directly bonded; Preferably, in formula (I), L is present or absent, and the optional L is a linking group formed by benzene leaving any two H capable of leaving; R 11 , R 12 , R 13 , R 31 , R 32 , R 33 , R 34 , R 41 , R 42 , R 43 and R 44 Each is independently selected from H, methyl, ethyl, n-propyl, isopropyl, methoxy, ethoxy, n-propoxy, isopropoxy, tert-butyl; X is S, O or -C(R 51 R 52 )-,R 51 , R 52 Each independently selected from C 1-6 or X does not exist so that the two phenyl groups are directly bonded.

3. The organic compound according to claim 2, characterized in that In formula (I), L may be present or absent, and L which is optionally present is 1,4-phenylene; R 11 , R 12 , R 13 , R 32 , R 33 , R 42 and R 43 Each is independently selected from H, methyl, ethyl, n-propyl, isopropyl, methoxy, ethoxy, n-propoxy, isopropoxy, tert-butyl; R 31 , R 34 , R 41 and R 44 All are H; X is S, O or -C(R 51 R 52 )-, R 51 , R 52 Each is independently selected from methyl, ethyl, n-propyl, isopropyl, tert-butyl, and phenyl; or X is absent so that the two phenyl groups are directly bonded.

4. The organic compound according to claim 3, characterized in that The structure shown in formula (I) is selected from any one of the following:

5. An amphiphilic polymer, characterized in that The amphiphilic polymer contains an A structural unit and a B structural unit; the A structural unit is a structural unit provided by at least one of the organic compounds described in any one of claims 1 to 4, and the B structural unit is a structural unit provided by a hydrophilic compound.

6. The amphiphilic polymer according to claim 5, characterized in that The hydrophilic compound is selected from at least one of polyethylene glycol monomethyl ether methacrylate and its homologues, polyethylene glycol monomethyl ether acrylate and its homologues, 3,4,5-tris-(polyethylene glycol monomethyl ether)benzyl alcohol methacrylate and its homologues, and 3,4,5-tris-(polyethylene glycol monomethyl ether)benzyl alcohol acrylate and its homologues.

7. The amphiphilic polymer according to claim 5 or 6, characterized in that The molar ratio of the A structural unit to the B structural unit is 1:0.001-1000; Preferably, the weight average molecular weight of the amphiphilic polymer is 600 to 500,000.

8. The amphiphilic polymer according to any one of claims 5 to 7, characterized in that The amphiphilic polymer is selected from any one of the following, and each x, each y, and each n are independently selected from positive integers of 1-1000, preferably each x, each y, and each n are independently selected from positive integers of 1-200:

9. Use of the organic compound according to any one of claims 1 to 4 and the amphiphilic polymer according to any one of claims 5 to 8 in aggregation-induced emission materials.

10. Use of the amphiphilic polymer according to any one of claims 5 to 8 in amphiphilic aggregation-induced emission polymer fluorescent materials with dual fluorescence emission.

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