CN110845714B - 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 PDF

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CN110845714B
CN110845714B CN201911133670.XA CN201911133670A CN110845714B CN 110845714 B CN110845714 B CN 110845714B CN 201911133670 A CN201911133670 A CN 201911133670A CN 110845714 B CN110845714 B CN 110845714B
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蒋其民
赵洁兰
江力
黄文艳
薛小强
杨宏军
蒋必彪
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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 Oxa-Michael addition polymerization of an alcoholic hydroxyl monomer containing tertiary amine and an unsaturated double bond or triple bond monomer containing amide. The obtained polymer has AIE characteristic and can be used for treating metal Fe3+The specific recognition, cationic property and good biocompatibility, and has wide application prospect in the fields of biological imaging, biological detection and gene/drug carriers.

Description

Water-soluble aggregation-induced emission polymer and preparation method and application thereof
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 movement in the molecule is limited, and electrons in an excited state can only return to a ground state in a radiation transition mode to show the phenomenon of enhancing fluorescence. The AIE material is widely applied to the fields of fluorescence sensing, biosensing, electroluminescence and the like. Since biological studies are usually carried out in an aqueous phase, water-soluble AIE materials are highly advantageous. 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:
Figure BDA0002279006570000021
formula 1:
in formula 1, the molecular skeleton contains a linear AIE polymer of tertiary amine and amide.
Figure BDA0002279006570000022
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 luminophores amides and tertiary luminophoresAmine group with 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, molecular weight distribution PDI 2.40, and is confirmed by infrared spectrum and nuclear magnetic spectrumA polymer of a target structure.
(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+The tertiary amine polymer prepared by the method can be used for detecting Fe by using plasma metal ions3+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%. Characterization of the weight-average molecular weight M of the Polymer by gel permeation chromatography in DMF phasew.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 polymers by gel permeation chromatography in DMF phaseWeight average molecular weight Mw.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 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 14.6mV, 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 (6)

1. A water-soluble aggregation-induced emission polymer for ion detection and biomedical fluorescent materials, wherein the structural formula of the emission polymer is shown as formula 1 and formula 2:
Figure DEST_PATH_IMAGE001
formula 1
Figure 688473DEST_PATH_IMAGE002
Formula 2;
the preparation method of the water-soluble aggregation-induced emission polymer comprises the following steps: dissolving a hydroxyl monomer containing a tertiary amine structure and an unsaturated bond monomer containing an amide bond in an organic solvent, and preparing a 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;
the hydroxyl monomer containing the tertiary amine structure is N-methyldiethanolamine or triethanolamine;
the unsaturated bond monomer containing amido bond is diacrylic acid amide or cysteamine.
2. The water-soluble aggregation-inducing luminescent polymer according to claim 1, wherein the molar amount of the unsaturated bond monomer is 1 to 2 times the molar amount of the hydroxyl group monomer having a tertiary amine structure.
3. The water-soluble aggregation-inducing luminescent polymer according to claim 1, wherein the organophosphazene base ist-BuP2Ort-BuP4The molar weight of the phosphazene base is 0.05 to 0.2 time of that of the monomer containing tertiary amine hydroxyl.
4. The water-soluble aggregation-inducing luminescent polymer according to claim 1, wherein the polymerization condition is a reaction temperature of 0 to 60%oAnd C, the polymerization time is 6-96 h.
5. The water-soluble aggregation-inducing luminescent polymer according to claim 1, wherein the organic solvent isN, N-dimethylformamide,N,N-dimethylacetamide, dimethylsulfoxide orN-methyl pyrrolidone, the molar amount of the solvent being 10-20 times the molar amount of the tertiary amine hydroxyl group-containing monomer.
6. The water-soluble aggregation-inducing luminescent polymer according to claim 1, wherein the fluorescence material for ion detection and biological application has a fluorescence state of a high concentration liquid or solid; the fluorescence test or ultraviolet excitation wavelength is 320-400 nm.
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