CN110845714A - Water-soluble aggregation-induced emission polymer and preparation method and application thereof - Google Patents
Water-soluble aggregation-induced emission polymer and preparation method and application thereof Download PDFInfo
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Abstract
The invention belongs to the field of non-traditional fluorescent polymers, and discloses a water-soluble aggregation-induced emission polymer, and a preparation method and application thereof. The water-soluble aggregation-induced emission polymer is prepared by performing Oxa-Michael addition polymerization on an alcoholic hydroxyl monomer containing tertiary amine and an unsaturated double bond or triple bond monomer containing amide. The obtained polymer not only has AIE characteristics, but also can be used for metallic Fe3+The specific recognition, the cationic and good biocompatibility, and the application prospect in the fields of biological imaging, biological detection and gene/drug carriers.
Description
Technical Field
The invention belongs to the field of non-traditional fluorescent polymers, and particularly relates to a water-soluble aggregation-induced emission polymer, and a preparation method and application thereof.
Background
In 2001, the team of the university of hong Kong science and technology, Tang-loyd college, discovered compounds with aggregation-induced emission (AIE) effect, when such fluorescent materials exist in a single molecule form in a solution, electrons in an excited state return to a ground state through intramolecular movement, and weak fluorescence is generated; when the molecule is in an aggregation state, the motion in the molecule is limited, and the electrons in an excited state can only return to a ground state in a radiation transition mode, so that the phenomenon of fluorescence enhancement is shown. The AIE material is widely applied to the fields of fluorescence sensing, biosensing, electroluminescence and the like. Water-soluble AIE materials are of great advantage because biological studies are usually performed in aqueous phase. Currently, the mainstream AIE polymer materials are constructed by molecular design of some hydrophobic molecules (such as cyclic polyene type, polyaromatic substituted ethylene type and pyran type molecules) containing large pi conjugated structure. Therefore, it is relatively difficult to prepare a water-soluble aggregation-inducing luminescent material by a simple polymerization system and method.
It has been found that a polymer containing an unconventional chromophore such as C ═ O, -COOR, and fatty amine does not emit light at a low solubility, emits intense light at a high concentration or in a solid state, and exhibits characteristics of AIE. Because the chemical structure of the macromolecule is closer to that of a common macromolecule, the macromolecule has good hydrophilicity, chain flexibility and structure adjustability, and has a plurality of advantages in constructing water-soluble AIE polymers. At present, the preparation method of the fluorescent polymer is mainly prepared by ring-opening polymerization and Michael addition polymerization of amino and unsaturated double bonds. However, the above-mentioned method for preparing polymers has the disadvantages of complicated synthesis steps, low efficiency and easy crosslinking. In addition, the mechanism of the fluorescent polymer is not sufficiently well studied because of the relatively few kinds of fluorescent polymers designed by the current preparation. Therefore, the research on the application of constructing a novel water-soluble nontraditional chromophore AIE polymer with an efficient and mild reaction system in different fields is a significant subject.
Disclosure of Invention
The invention aims at the defects of the preparation method and the application of the aggregation-induced emission polymer, and provides a water-soluble aggregation-induced emission polymer and the preparation method and the application thereof.
In order to achieve the above object, according to one aspect of the present invention, there is provided a water-soluble aggregation-inducing luminescent polymer characterized by structural formulae 1 and 2:
formula 1:
in formula 1, the molecular skeleton contains a linear AIE polymer of tertiary amine and amide.
Formula 2
In formula 2, the molecular backbone contains branched AIE polymers of tertiary amines and amides.
According to another aspect of the present invention, a preparation method of a water-soluble aggregation-induced emission polymer is provided, wherein a hydroxyl monomer containing a tertiary amine structure and an unsaturated bond monomer containing an amide bond are dissolved in an organic solvent, and the water-soluble aggregation-induced emission polymer is prepared under mild conditions through Oxa-Michael addition click polymerization of hydroxyl and a double bond catalyzed by an organic phosphazene base.
Wherein, the hydroxyl monomer containing the tertiary amine structure is N-methyldiethanolamine or triethanolamine; the unsaturated bond monomer containing the amide bond is bisacrylamide and cysteamine, and the molar weight of the unsaturated bond monomer is 1-2 times of that of the hydroxyl monomer containing the tertiary amine structure;
the organic base is phosphazene base t-BuP2Or t-BuP4(ii) a The molar weight of the phosphazene base is 0.05 to 0.2 time of that of the monomer containing tertiary amine hydroxyl;
the polymerization condition is that the reaction temperature is 0-60 ℃, and the polymerization time is 6-96 h;
the organic solvent is N, N-dimethylformamide, N-dimethylacetamide, dimethyl sulfoxide or N-methylpyrrolidone, and the molar weight of the solvent is 10-20 times of that of the tertiary amine hydroxyl monomer;
the third aspect of the present invention: provides a fluorescent material which is prepared by adopting the AIE polymer and can be used for ion detection and biomedical use.
The fluorescence-containing luminescent material for ion detection and biological application is in a high-concentration liquid state (>10mg/ml) or a solid state; the fluorescence test or ultraviolet excitation wavelength is 320-400 nm.
Has the advantages that:
the water-soluble aggregation-induced emission polymer synthesized by the invention is prepared by Oxa-Michael click polymerization, the monomer is stable, has no pungent smell and rich sources, and the polymerization system has simple and stable components and is easy to operate. The polymer aggregation induced emission is derived from unconventional luminol amide and tertiary amine groups, and has good biocompatibility, water solubility, cationic property and Fe3+And specific recognition provides a foundation for the application of the polymer in the fields of ion detection and gene/drug carriers.
Drawings
FIG. 1 is an infrared spectrum of a water-soluble AIE polymer (B-1) obtained in example 1.
FIG. 2 is a nuclear magnetic hydrogen spectrum of the water-soluble AIE polymer (B-1) obtained in example 1 in 4% deuterated hydrochloric acid.
FIG. 3 is a fluorescence spectrum (A) and an image (B) under 365nm ultraviolet irradiation of the water-soluble AIE polymer (B-1) obtained in example 1.
FIG. 4 is a fluorescence spectrum (A) of the water-soluble AIE polymer (B-2) obtained in example 2 at various concentrations and an image (B) taken under 365nm ultraviolet light.
FIG. 5 is a fluorescence spectrum of the water-soluble AIE polymers obtained in example 3(B-3), example 4(B-4) and example 5(L-1) at an aqueous solution of 100mg/mL, in which the excitation wavelength tested was 371 nm.
FIG. 6 shows the toxicity of the water-soluble AIE polymers obtained in example 1(B-1) and example 2(B-2) in HeLa cells.
FIG. 7 shows the water-soluble AIE polymer obtained in example 1 at 10-2A fluorescence spectrum diagram in a metal ion water solution of mol/L.
Detailed Description
The present invention will be described in detail with reference to examples.
Example 1
(1) Triethanolamine (0.149g, 1mmol), bisacrylamide (0.154g, 1mmol) and N, N-dimethylformamide (2.38g,20mmol) were added to a polymerization flask, followed by addition of catalyst t-BuP to the polymerization flask under argon protection at a rate of 0-5s per drop2(100. mu.L, 0.2mmol) and reacted at 25 ℃ for 48 h. After the reaction, acetic acid was added to terminate the reaction, and methylene chloride was added to dilute the reaction solution, followed by settling in n-hexane to obtain a branched polymer (B-1) with a yield of 90%. Characterization of the weight-average molecular weight M of the Polymer by gel permeation chromatography in DMF phasew.GPC74000g/mol, the molecular weight distribution PDI is 2.40, and the infrared spectrum and the nuclear magnetic spectrum are adopted to confirm that the polymer with the target structure is prepared.
(2) The fluorescence properties of the polymer in aqueous solution at different concentrations are tested by a fluorescence microscope at the wavelength of 371nm, and the polymer shows weak fluorescence at low concentration and strong fluorescence at high concentration or solid state and has the characteristics of AIE. The potential of the polymer tested by a zeta potential meter is 17.6mV, which shows that the fluorescent polymer with water-solubility and cationic AIE effect is successfully prepared by click polymerization of hydroxyl and carbon-carbon double bonds.
(3) The obtained AIE polymer is prepared into 10 percent serum culture medium solutions with different concentrations to be co-cultured with HeLa cells, and compared with cationic polymer PEI (25KDa), the polymer material prepared by click polymerization of hydroxyl and double bonds has lower toxicity and is suitable for application in the field of biomedicine.
(4) Preparing water-soluble AIE polymer with a certain concentration by adding Na as metal ion+，K+，Ca2+，Mg2+，Fe2+，Fe3+，Al3+,Cu2+Detection of plasma metal ions, tertiary amine polymers prepared by the methodCan be aligned with Fe3+And (3) specific recognition, which can be applied to ion detection.
Example 2
(1) Triethanolamine (0.149g, 1mmol), N' -cysteamine (0.260g, 1mmol) and N, N-dimethylformamide (2.38g,20mmol) were added to a polymerization flask, followed by addition of catalyst t-BuP at a rate of 0-5s per drop to the flask under argon protection2(100. mu.L, 0.2mmol) and reacted at 25 ℃ for 48 h. After the reaction, acetic acid was added to terminate the reaction, and methylene chloride was added to dilute the reaction solution, followed by settling in n-hexane to obtain a branched polymer (B-2) in a yield of 84%. Characterization of the weight-average molecular weight M of the Polymer by gel permeation chromatography in DMF phasew.GPC72000g/mol, the molecular weight distribution PDI is 2.43, and the infrared spectrum and the nuclear magnetic spectrum are adopted to confirm that the polymer with the target structure is prepared.
(2) The fluorescence properties of the polymer in aqueous solutions with different concentrations are tested at the wavelength of 371nm by using a fluorescence microscope or irradiated by 365nm ultraviolet light, and the polymer shows weak fluorescence at low concentration and strong fluorescence at high concentration or in a solid state, and has the characteristics of AIE. The potential of the polymer was measured to be 16.2mV using a zeta-potentiometer, indicating that a fluorescent polymer with water-soluble, cationic AIE effect was successfully prepared by click polymerization of hydroxyl groups and carbon-carbon double bonds.
(3) The obtained AIE polymer is prepared into 10 percent serum culture medium solutions with different concentrations to be co-cultured with HeLa cells, and compared with cationic polymer PEI (25K Da), the polymer material prepared by click polymerization of hydroxyl and double bonds has lower toxicity and is suitable for application in the biomedical field.
Example 3
(1) Triethanolamine (0.149g, 1mmol), bisacrylamide (0.154g, 1mmol) and N, N-dimethylformamide (2.38g,20mmol) were added to a polymerization flask, followed by addition of catalyst t-BuP to the polymerization flask under argon protection at a rate of 0-5s per drop2(100. mu.L, 0.2mmol) and reacted at 25 ℃ for 12 h. After the reaction, acetic acid was added to terminate the reaction, and the reaction mixture was diluted with methylene chloride and precipitated in n-hexane to obtain a branched polymer (B-3) in a yield of 88%. Gelfiltration with DMF phaseCharacterization of the weight-average molecular weight M of the Polymer by transmission chromatographyw.GPC27300g/mol, molecular weight distribution PDI 1.60. It showed strong fluorescence at high concentration (100mg/mL) or in the solid state, and its polymer had the characteristics of AIE, tested with a fluorescence microscope at a wavelength of 371 nm. The potential of the polymer tested by a zeta potential meter is 14.5mV, which shows that the fluorescent polymer with water-solubility and cationic AIE effect is successfully prepared by click polymerization of hydroxyl and carbon-carbon double bonds.
Example 4
(1) Triethanolamine (0.149g, 1mmol), bisacrylamide (0.154g, 1mmol) and N, N-dimethylformamide (2.38g,20mmol) were added to a polymerization flask, followed by addition of catalyst t-BuP to the polymerization flask under argon protection at a rate of 0-5s per drop2(100. mu.L, 0.2mmol) and reacted at 25 ℃ for 24 h. After the reaction, acetic acid was added to terminate the reaction, and the reaction mixture was diluted with methylene chloride and precipitated in n-hexane to obtain a branched polymer (B-4) in a yield of 86%. Characterization of the weight-average molecular weight M of the Polymer by gel permeation chromatography in DMF phasew.GPC32700g/mol, molecular weight distribution PDI 1.89, which exhibits strong fluorescence at high concentration (100mg/mL) or in the solid state, tested with a fluorescence microscope at a wavelength of 371nm, and whose polymer has the properties of AIE. The potential of the polymer tested by a zeta potential meter is 16.2mV, which shows that the fluorescent polymer with water-solubility and cationic AIE effect is successfully prepared by click polymerization of hydroxyl and carbon-carbon double bonds.
Example 5
(1) N-methyldiethanolamine (0.119g, 1mmol), bisacrylamide (0.154g, 1mmol) and N, N-dimethylformamide (1.19g,10mmol) were added to a polymerization flask, followed by addition of catalyst t-BuP at a rate of 0-5s per drop to the polymerization flask under argon protection2(50. mu.L, 0.1mmol) and reacted at 25 ℃ for 96 h. After the reaction, acetic acid was added to terminate the reaction, and then methylene chloride was added to dilute the reaction solution, followed by settling in n-hexane to obtain a linear polymer (L-1) with a yield of 75%. Characterization of the weight-average molecular weight M of the Polymer by gel permeation chromatography in DMF phasew.GPC18000g/mol, molecular weight distribution PDI 1.3. It was tested at high wavelength 371nm using a fluorescence microscopeShows stronger fluorescence at a concentration (100mg/mL) or in a solid state, and the polymer thereof has the characteristics of AIE. The potential of the polymer tested by a zeta potential meter is 14.6mV, which shows that the fluorescent polymer with water-solubility and cationic AIE effect is successfully prepared by click polymerization of hydroxyl and carbon-carbon double bonds.
Claims (9)
1. A water-soluble aggregation-induced emission polymer, wherein the structure of the emission polymer is represented by formula 1 and formula 2:
2. a method for preparing the water-soluble aggregation-inducing luminescent polymer according to claim 1, wherein the method comprises: dissolving a hydroxyl monomer containing a tertiary amine structure and an unsaturated bond monomer containing an amide bond in an organic solvent, and preparing the water-soluble aggregation-induced emission polymer under mild conditions by using organic phosphazene base to catalyze Oxa-Michael addition click polymerization of hydroxyl and double bonds.
3. The method according to claim 2, wherein the hydroxyl monomer containing a tertiary amine structure is N-methyldiethanolamine or triethanolamine.
4. The method for preparing a water-soluble aggregation-inducing luminescent polymer according to claim 2, wherein the unsaturated bond monomer containing the amide bond is bisacrylamide or cysteamine, and the molar amount of the unsaturated bond monomer is 1 to 2 times that of the hydroxyl monomer containing the tertiary amine structure.
5. The method for preparing a water-soluble aggregation-inducing luminescent polymer according to claim 2, wherein the organophosphazene base is t-BuP2Or t-BuP4The molar weight of the phosphazene base is tertiary amine hydroxyl-containing monomer0.05-0.2 times of the molar weight.
6. The method for preparing a water-soluble aggregation-inducing luminescent polymer according to claim 2, wherein the polymerization conditions are a reaction temperature of 0 to 60 ℃ and a polymerization time of 6 to 96 hours.
7. The method for preparing a water-soluble aggregation-inducing luminescent polymer according to claim 2, wherein the organic solvent is N, N-dimethylformamide, N-dimethylacetamide, dimethylsulfoxide or N-methylpyrrolidone, and the molar amount of the solvent is 10 to 20 times that of the tertiary amine hydroxyl group-containing monomer.
8. The use of the water-soluble aggregation-inducing luminescent polymer according to claim 1, wherein the luminescent polymer is used for ion detection and biomedical fluorescent materials.
9. The use of the water-soluble aggregation-inducing luminescent polymer according to claim 8, wherein the fluorescence-containing material for ion detection and biological applications is in a high-concentration liquid or solid state;
the fluorescence test or ultraviolet excitation wavelength is 320-400 nm.
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| CN114716659A (en) * | 2022-05-17 | 2022-07-08 | 常州大学 | Method for preparing nitrogen-containing polymer through click polymerization without catalyst |
| CN114736363A (en) * | 2022-05-17 | 2022-07-12 | 常州大学 | Fluorescent polymer and method for regulating and controlling luminescent color of fluorescent polymer |
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| CN114716659B (en) * | 2022-05-17 | 2023-12-12 | 常州大学 | Method for preparing nitrogen-containing polymer through click polymerization without catalyst |
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