CN102964767A - Fluorescent conjugated polymer and magnetic nanoparticle composite material and preparation method thereof - Google Patents
Fluorescent conjugated polymer and magnetic nanoparticle composite material and preparation method thereof Download PDFInfo
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Abstract
The invention provides a fluorescent conjugated polymer and magnetic nanoparticle composite material and a preparation method thereof. Suzuki reaction is carried out for preparing conjugated polymer with fluorescent property, and the conjugated polymer is prepared into an alpha-bromine macromolecule initiator, so as to initiate atom transfer radical polymerization of tert-butyl acrylate and obtain a molecular brush type fluorescent conjugated polymer, and the molecular brush type polymer is hydrolyzed to obtain a molecular brush type water soluble conjugated polymer rich in carboxyl; with ferric acetylacetonate (III), 1,2-hexadecanediol, oleic acid and oleyamine as raw materials, the magnetic nanoparticles with uniform particle size are prepared in dibenzyl ether by adopting a high temperature solvent method; with the molecular brush type water soluble fluorescent conjugated polymer containing carboxyl as a ligand, the oleic acid on the surfaces of iron oxide magnetic nanoparticles is displaced in tetrahydrofuran, and then spare carboxyl is salinized, so that fluorescent and magnetic water soluble molecular brush type conjugated polymer/magnetic nanoparticle composite material is obtained.
Description
Technical field
The invention belongs to biological functional material technology field, be specifically related to a class and have the molecular brush type water soluble fluorescent conjugated polymer of photoluminescent property and magnetic/magnetic nanometer composite manufacture method.
Technical background
Magnetic nano-particle is widely used in the biological fields such as NMR contrast agent, medicament transport, magnetic thermotherapy because it has the advantages such as good biocompatibility, hypotoxicity and superparamagnetism.The present invention proposes by the part displacement molecular brush type soluble conjugated polymer to be incorporated into the magnetic nanometer surface, has obtained molecular brush type soluble conjugated polymer/magnetic nanometer matrix material.The magnetic Nanosurface, the introducing of molecular brush type soluble conjugated polymer has not only improved the water-soluble and biocompatibility of magnetic nanometer, has also realized the combination of magnetic and fluorescence simultaneously, thereby has widened the application of magnetic nanometer at biological field.The carboxyl that molecular brush type soluble conjugated polymer/magnetic nano composite material rich surface is remaining can further be introduced the biologic specificity group.
Summary of the invention
Technical problem: the present invention relates to the molecular brush type water soluble fluorescent conjugated polymer that a class has photoluminescent property and magnetic/magnetic nanometer composite manufacture method.
Technical scheme: the molecular brush type soluble conjugated polymer with fluorescence and magnetic, multi-functional of the present invention/magnetic nanometer matrix material, has good biocompatibility, and can realize simultaneously fluorescence imaging and nuclear magnetic resonance, can be widely used in the fields such as drug targeting release, magnetic thermotherapy, bioluminescence detection.
Fluorescent conjugated polymer of the present invention and magnetic nanometer matrix material are to have the molecular brush type soluble conjugated polymer of fluorescence and magnetic, multi-functional and the matrix material of magnetic nanometer, its structure is: centronucleus is magnetic nanometer, and part is the molecular brush type soluble conjugated polymer of photoluminescent property.
Magnetic nanometer is the oxide compound of Fe, Co or Mn metal, and particle diameter and has monodispersity between 1-100nm.
Described conjugated polymers is the rich carboxylic poly-fluorenes benzene class fluorescence molecule brush of a class, and its concrete structure is as follows:
The polymerization degree x of main chain conjugated polymers is 6-30;
The polyacrylic polymerization degree n of molecular brush side chain is 10-200;
Molecular brush type polymkeric substance passes through-COO
-Base links with the magnetic nanometer surface.
Fluorescent conjugated polymer of the present invention and magnetic nanometer composite manufacture method may further comprise the steps,
1) magnetic nanometer is synthetic
Take dibenzyl ether as solvent, with ferric acetyl acetonade (III), 1,2-16 glycol, oleic acid and oleyl amine are raw material, adopt the standby monodispersed magnetic nanometer of the hot legal system of high-temperature solvent:
Concrete steps are as follows:
With ferric acetyl acetonade (III), 1,2-16 glycol, oleic acid and oleyl amine add in the dibenzyl ether, magnetic force uniform stirring in the nitrogen protection, mixing solutions is heated to 150-220 ℃ of lasting 1-3 hour, then temperature is raised to 280-320 ℃ and reheats 0.5-1 hour, be cooled to room temperature, add a small amount of ethanol, have black precipitate to generate; Adopt centrifugal-dissolving-centrifugal method to prepare the higher product of purity, the magnetic nanometer product is through behind the drying under reduced pressure, is kept in 0-4 ℃ the refrigerator for subsequent use;
2) rich carboxylic molecular brush type soluble conjugated polymer is synthetic
Under the nitrogen atmosphere, Isosorbide-5-Nitrae-to benzene hypoboric acid ester, 2,7-, two bromo-9,9-two (3-hydroxypropyl) fluorenes, Pd (PPh
3)
4Add in the toluene solution, injection is dissolved with K
2CO
3The aqueous solution; This solution fully stirred three days under 85-95 ℃ of condition, then added phenylo boric acid reaction 7-9 hour, added at last bromobenzene, reacted after 12-24 hour stopped reaction; After removing toluene, residuum is dissolved in the tetrahydrofuran (THF), after the neutral post of aluminium sesquioxide was removed remaining catalyzer, solution was concentrated, and sedimentation is 24 times in methanol solution, must have the fluorescent conjugated polymer of photoluminescent property;
Under the nitrogen atmosphere, conjugated polymers is dissolved in the dry tetrahydrofuran (THF), after polymkeric substance dissolves fully, injects triethylamine, under the ice bath, add 2-bromine isobutyl acylbromide, then rise to room temperature, continue to stir 24-36 hour; React complete after, filter out the hydrochloride precipitation of triethylamine, concentrated filtrate obtains pale yellow powder shape solid after sedimentation 2-3 time in methyl alcohol, vacuum-drying obtains having the conjugated polymers macromole evocating agent of photoluminescent property;
In the Schelek pipe, add conjugated polymers macromole evocating agent, cuprous bromide; Vacuumize, logical nitrogen repeats 2-4 time; Add methyl-phenoxide dissolve polymer macromole evocating agent, then add: N, N, N ', N, ' N " five methyl diethylentriamine (PMDETA) stirs and is heated to 90-110 ℃; then inject tert-butyl acrylate in reaction system, reacts after 12-24 hour stopped reaction; In solution, add methylene dichloride, solution is removed mantoquita by the neutral alumina chromatography column, use the Rotary Evaporators concentrated solution to thickness, and sedimentation in normal hexane, this operation 2-4 time repeated; Dry in 30-50 ℃ of vacuum drying oven, obtain main chain and be poly-fluorenes benzene, side chain is the molecular brush type conjugated polymers of the polyacrylic acid tert-butyl ester;
In the nitrogen atmosphere, molecular brush type conjugated polymers is dissolved in the tetrahydrofuran (THF), under the room temperature, adds trifluoroacetic acid, reaction continues to steam solvent after 12-24 hour, obtains main chain and is poly-fluorenes benzene, and side chain is polyacrylic molecular brush soluble conjugated polymer;
3) molecular brush type water soluble fluorescent conjugated polymer and magnetic nanometer composite manufacture
Magnetic nanometer and the molecular brush type soluble conjugated polymer of oleic acid parcel are dissolved in the tetrahydrofuran (THF), 35-55 ℃ of lower the stirring 24-36 hour, then the centrifugal chocolate precipitation that obtains is scattered in throw out in the aqueous solution, slowly adds Na
2CO
3The aqueous solution stirred 2-4 hour, and after mixed solution was put into dialysis tubing and dialysed 48-72 hour, lyophilize obtained molecular brush type water soluble fluorescent conjugated polymer and magnetic nanometer matrix material.
Beneficial effect: that molecular brush type water soluble fluorescent conjugated polymer/the magnetic nanometer matrix material shows is water-soluble, biocompatibility and good fluorescence property and magnetic property, has good application in biology.
Description of drawings
Fig. 1 is Fe
3O
4The FTIR of@PFB-g-PAA,
Fig. 2 is the transmission electron microscope figure of polymkeric substance/magnetic nanometer,
Fig. 3 is the dynamic particle diameter scatter diagram of polymkeric substance/magnetic nanometer,
Fig. 4 is that the UV, visible light of polymkeric substance/magnetic nanometer in water absorbs (UV) spectrum,
Fig. 5 is photoluminescence (PL) spectrum of polymkeric substance/magnetic nanometer in water,
Fig. 6 is polymkeric substance/magnetic nanometer superconductive quantum interference figure (SQUID),
Fig. 7 is the structural representation of matrix material of the present invention,
Be the magnetic nanometer centronucleus;
For having the molecular brush type soluble conjugated polymer of photoluminescent property.
Embodiment
Described magnetic nanometer is Fe
3O
4Nanoparticle, particle diameter and have monodispersity between 4-10nm.
Described fluorescent conjugated polymer is the rich carboxylic poly-fluorenes benzene class fluorescence molecule brush of a class, and its concrete structure is as follows:
The polymerization degree x of main chain conjugated polymers is 6-30;
The polyacrylic polymerization degree n of molecular brush side chain is 10-200;
Molecular brush type conjugated polymers links with the magnetic nanometer surface by-COO-base.
Described molecular brush type water soluble fluorescent conjugated polymer/magnetic nanometer matrix material is by the carboxylic molecular brush type of richness soluble conjugated polymer replacement of fe
3O
4The oleic acid of nanoparticle surface and obtaining.
The synthetic method of above-mentioned matrix material of the present invention is as follows:
(1) magnetic nanometer is synthetic
Take dibenzyl ether as solvent, with ferric acetyl acetonade (III), 1,2-16 glycol, oleic acid and oleyl amine are raw material, adopt the standby monodispersed magnetic nanometer of high-temperature solvent legal system:
Concrete steps are as follows:
With ferric acetyl acetonade (III), 1; 2-16 glycol, oleic acid and oleyl amine add in the dibenzyl ether; magnetic agitation is even in the nitrogen protection; mixing solutions is heated to 150-220 ℃ of lasting 1-3 hour; then temperature is raised to 280-320 ℃ and reheats 0.5-1 hour; be cooled to room temperature, add a small amount of ethanol, have black precipitate to generate.Adopt centrifugal-dissolving-centrifugal method to prepare the higher product of purity, the magnetic nanometer product is through behind the drying under reduced pressure, is kept in 0-4 ℃ the refrigerator for subsequent use;
(2) rich carboxylic molecular brush type soluble conjugated polymer is synthetic
Under the nitrogen atmosphere, Isosorbide-5-Nitrae-to benzene hypoboric acid ester, 2,7-, two bromo-9,9-two (3-hydroxypropyl) fluorenes, Pd (PPh
3)
4Add in the toluene solution, injection is dissolved with K
2CO
3The aqueous solution.This solution fully stirred three days under 85-95 ℃ of condition, then added phenylo boric acid reaction 7-9 hour, added at last bromobenzene, reacted after 12-24 hour stopped reaction.After removing toluene, residuum is dissolved in the tetrahydrofuran (THF), after the neutral post of aluminium sesquioxide was removed remaining catalyzer, solution was concentrated, and sedimentation is 2-4 time in methanol solution, must have the fluorescent conjugated polymer of photoluminescent property.
Under the nitrogen atmosphere, conjugated polymers is dissolved in the dry tetrahydrofuran (THF), after polymkeric substance dissolves fully, injects triethylamine, under the ice bath, add 2-bromine isobutyl acylbromide, then rise to room temperature, continue to stir 24-36 hour.React complete after, filter out the hydrochloride precipitation of triethylamine.Concentrated filtrate obtains pale yellow powder shape solid, vacuum-drying after the sedimentation three times in methyl alcohol.Obtain having the conjugated polymers macromole evocating agent of photoluminescent property.
In the Schelek pipe, add conjugated polymers macromole evocating agent, cuprous bromide.Vacuumize, logical nitrogen repeats 2-4 time.Add methyl-phenoxide dissolve polymer macromole evocating agent, then add: N, N, N', N, " five methyl diethylentriamine (PMDETA) stirs and is heated to 90-110 ℃; then inject tert-butyl acrylate in reaction system to ' N, reacts after 12-24 hour stopped reaction.In solution, add methylene dichloride, solution is removed mantoquita by the neutral alumina chromatography column.With the Rotary Evaporators concentrated solution to thickness, and sedimentation in normal hexane.Repeat this operation three times.Dry in 30-50 ℃ of vacuum drying oven, obtain main chain and be poly-fluorenes benzene, side chain is the polymer molecule brush of the polyacrylic acid tert-butyl ester.
In the nitrogen atmosphere, the conjugated polymers molecular brush is dissolved in the tetrahydrofuran (THF).Under the room temperature, add trifluoroacetic acid.Reaction continues to steam solvent after 12-24 hour.Obtain main chain and be poly-fluorenes benzene, side chain is polyacrylic molecular brush soluble conjugated polymer.
(3) molecular brush type water soluble fluorescent conjugated polymer/magnetic nanometer composite manufacture
Magnetic nanometer and the molecular brush soluble conjugated polymer of oleic acid parcel are dissolved in the tetrahydrofuran (THF) 35-55 ℃ of lower the stirring 24-36 hour, the then centrifugal chocolate precipitation that obtains.Throw out is scattered in the aqueous solution, slowly adds Na
2CO
3The aqueous solution stirred 2-3 hour, after mixed solution is put into dialysis tubing and dialysed 48-72 hour, and lyophilize.Obtain molecular brush type water soluble fluorescent conjugated polymer/magnetic nanometer matrix material.
In order to understand better the present invention, further specify technical scheme of the present invention below by specific embodiment.
Embodiment 1, molecular brush type water soluble fluorescent conjugated polymer/magnetic nanometer composite manufacture
(1) Fe
3O
4Synthesizing of magnetic nanometer
With 1; 2-16 glycol (6.461g; 25mmol), oleic acid (4.761mL, 15mmol); oleyl amine (4.012g; 4.935mL, 15mmol), ferric acetyl acetonade (III) (1.766g; 5mmol) and dibenzyl ether (50mL) join successively in the there-necked flask of 250mL violent stirring 0.5 hour in the nitrogen protection under the room temperature.Temperature is raised to 200 ℃ of heating 2 hours, and then temperature continues to be raised to 300 ℃ and reheats 1 hour.Remove heating jacket relief mixing solutions and naturally cool to room temperature, ethanol (100mL) is joined in the mixture, moment has produced black precipitate, obtains the higher black powder of purity by centrifugal-dissolving-centrifugal method, i.e. magnetic nanometer (the Fe of oleic acid parcel
3O
4@OA), behind the drying under reduced pressure it is kept in the refrigerator (0-4 ℃).
(2) contain the synthetic of carboxyl molecular brush type soluble conjugated polymer
Under the nitrogen atmosphere, Isosorbide-5-Nitrae-to benzene hypoboric acid ester (0.16g, 0.5mmol), 2,7-, two bromo-9,9-two (3-hydroxypropyl) fluorenes (0.22g, 0.5mmol), 1mol%Pd (PPh
3)
4Add in the toluene solution of 12mL, injection is dissolved with 0.4g K
2CO
3The 2mL aqueous solution.This solution fully stirred three days under 85 ℃ of conditions.The phenylo boric acid of 5%mol adds in this solution.After 8 hours, the 5%mol bromobenzene adds in this reaction solution.After 16 hours, stopped reaction.After removing toluene, residuum is dissolved in the tetrahydrofuran (THF), after the neutral post of aluminium sesquioxide was removed remaining catalyzer, solution was concentrated, and sedimentation is three times in methanol solution, the final 0.20g product (PFB) that gets.Productive rate: 59.7%.
Under the nitrogen atmosphere, 0.1g PFB is dissolved in the tetrahydrofuran (THF) of 5mL drying, after polymkeric substance dissolves fully, injects the 0.3g triethylamine, and reaction is placed ice-water bath, and 0.2g 2-bromine isobutyl acylbromide slowly injects.Rise to room temperature, continue to stir 24 hours.In reaction process, can observe the adularescent Precipitation.React complete after, filter out the hydrochloride precipitation of triethylamine.Concentrated filtrate obtains pale yellow powder shape solid, vacuum-drying after the sedimentation three times in methyl alcohol.The final solid (PFB-Br) that gets.Productive rate: 75%.
In 20mL Schelek pipe, add PFB-Br(48mg), CuBr(14mg).Vacuumize logical nitrogen, triplicate.Add methyl-phenoxide (6mL) dissolving, then add PMDETA(21 μ L), can observe solution colour and become light green.Stirring also is heated to 110 ℃.The TBA of 3mL is injected fast.Reaction continued after 12 hours, and solution becomes gets thickness, stopped reaction.Add the methylene dichloride of 10mL in the solution, solution is removed mantoquita by the neutral alumina chromatography column.With the Rotary Evaporators concentrated solution to thickness, and sedimentation in normal hexane.Repeat this operation three times.Dry in 40 ℃ of vacuum drying ovens, the final faint yellow solid (PFB-g-PTBA) that gets.Productive rate 70%.
In the nitrogen atmosphere, the PFB-g-TBA of 0.3g is dissolved in the tetrahydrofuran (THF).Under the room temperature, add the 3mL trifluoroacetic acid.Reaction continues to steam solvent after 12 hours.Obtain main chain and be poly-fluorenes benzene, side chain is polyacrylic polymer molecule brush (PFB-g-PAA).
(3) molecular brush water soluble fluorescent conjugated polymer/magnetic nanometer composite manufacture
Magnetic nanometer 100mg and conjugated polymers molecular brush (PFB-g-PAA) 300mg of oleic acid parcel are dissolved among the 10mL THF 40 ℃ of lower stirrings 24 hours, the then centrifugal chocolate precipitation that obtains.Throw out is scattered in the 100mL aqueous solution, slowly adds 10g Na
2CO
3, stirred 2 hours, after mixed solution is put into dialysis tubing and dialysed 72 hours, lyophilize.Obtain molecular brush type water soluble fluorescent conjugated polymer/magnetic nanometer matrix material.
Claims (4)
1. a fluorescent conjugated polymer and magnetic nanometer matrix material, it is characterized in that, this matrix material is to have the molecular brush type soluble conjugated polymer of fluorescence and magnetic, multi-functional and the matrix material of magnetic nanometer, its structure is: centronucleus is magnetic nanometer, and part is the molecular brush type soluble conjugated polymer of photoluminescent property.
2. fluorescent conjugated polymer according to claim 1 and magnetic nanometer matrix material is characterized in that, magnetic nanometer is the oxide compound of Fe, Co or Mn metal, and particle diameter and has monodispersity between 1-100nm.
3. fluorescent conjugated polymer according to claim 1 and magnetic nanometer matrix material is characterized in that, described conjugated polymers is the rich carboxylic poly-fluorenes benzene class fluorescence molecule brush of a class, and its concrete structure is as follows:
The polymerization degree x of main chain conjugated polymers is 6-30;
The polyacrylic polymerization degree n of molecular brush side chain is 10-200;
Molecular brush type polymkeric substance links with the magnetic nanometer surface by-COO-base.
4. a fluorescent conjugated polymer as claimed in claim 1 and magnetic nanometer composite manufacture method is characterized in that this preparation method may further comprise the steps,
1) magnetic nanometer is synthetic
Take dibenzyl ether as solvent, with ferric acetyl acetonade (III), 1,2-16 glycol, oleic acid and oleyl amine are raw material, adopt the standby monodispersed magnetic nanometer of the hot legal system of high-temperature solvent:
Concrete steps are as follows:
With ferric acetyl acetonade (III), 1,2-16 glycol, oleic acid and oleyl amine add in the dibenzyl ether, magnetic force uniform stirring in the nitrogen protection, mixing solutions is heated to 150-220 ℃ of lasting 1-3 hour, then temperature is raised to 280-320 ℃ and reheats 0.5-1 hour, be cooled to room temperature, add a small amount of ethanol, have black precipitate to generate; Adopt centrifugal-dissolving-centrifugal method to prepare the higher product of purity, the magnetic nanometer product is through behind the drying under reduced pressure, is kept in 0-4 ℃ the refrigerator for subsequent use;
2) rich carboxylic molecular brush type soluble conjugated polymer is synthetic
Under the nitrogen atmosphere, Isosorbide-5-Nitrae-to benzene hypoboric acid ester, 2,7-, two bromo-9,9-two (3-hydroxypropyl) fluorenes, Pd (PPh
3)
4Add in the toluene solution, injection is dissolved with K
2CO
3The aqueous solution; This solution fully stirred three days under 85-95 ℃ of condition, then added phenylo boric acid reaction 7-9 hour, added at last bromobenzene, reacted after 12-24 hour stopped reaction; After removing toluene, residuum is dissolved in the tetrahydrofuran (THF), after the neutral post of aluminium sesquioxide was removed remaining catalyzer, solution was concentrated, and sedimentation is 2-4 time in methanol solution, must have the fluorescent conjugated polymer of photoluminescent property;
Under the nitrogen atmosphere, conjugated polymers is dissolved in the dry tetrahydrofuran (THF), after polymkeric substance dissolves fully, injects triethylamine, under the ice bath, add 2-bromine isobutyl acylbromide, then rise to room temperature, continue to stir 24-36 hour; React complete after, filter out the hydrochloride precipitation of triethylamine, concentrated filtrate obtains pale yellow powder shape solid after sedimentation 2-3 time in methyl alcohol, vacuum-drying obtains having the conjugated polymers macromole evocating agent of photoluminescent property;
In the Schelek pipe, add conjugated polymers macromole evocating agent, cuprous bromide; Vacuumize, logical nitrogen repeats 2-4 time; Add methyl-phenoxide dissolve polymer macromole evocating agent, then add: N, N, N ', N, ' N " five methyl diethylentriamine (PMDETA) stirs and is heated to 90-110 ℃; then inject tert-butyl acrylate in reaction system, reacts after 12-24 hour stopped reaction; In solution, add methylene dichloride, solution is removed mantoquita by the neutral alumina chromatography column, use the Rotary Evaporators concentrated solution to thickness, and sedimentation in normal hexane, this operation 2-4 time repeated; Dry in 30-50 ℃ of vacuum drying oven, obtain main chain and be poly-fluorenes benzene, side chain is the molecular brush type conjugated polymers of the polyacrylic acid tert-butyl ester;
In the nitrogen atmosphere, molecular brush type conjugated polymers is dissolved in the tetrahydrofuran (THF), under the room temperature, adds trifluoroacetic acid, reaction continues to steam solvent after 12-24 hour, obtains main chain and is poly-fluorenes benzene, and side chain is polyacrylic molecular brush soluble conjugated polymer;
3) molecular brush type water soluble fluorescent conjugated polymer and magnetic nanometer composite manufacture
Magnetic nanometer and the molecular brush type soluble conjugated polymer of oleic acid parcel are dissolved in the tetrahydrofuran (THF), 35-55 ℃ of lower the stirring 24-36 hour, then the centrifugal chocolate precipitation that obtains is scattered in throw out in the aqueous solution, slowly adds Na
2CO
3The aqueous solution stirred 2-4 hour, and after mixed solution was put into dialysis tubing and dialysed 48-72 hour, lyophilize obtained molecular brush type water soluble fluorescent conjugated polymer and magnetic nanometer matrix material.
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| CN110760024A (en) * | 2019-10-31 | 2020-02-07 | 南京邮电大学 | Near-infrared two-region fluorescence imaging polymer and preparation method and application thereof |
| CN110760024B (en) * | 2019-10-31 | 2021-09-28 | 南京邮电大学 | Near-infrared two-region fluorescence imaging polymer and preparation method and application thereof |
| CN113368045A (en) * | 2021-05-25 | 2021-09-10 | 江苏大学 | Magnetic oxidation response drug-loaded nano micelle and preparation method and application thereof |
| CN114426842A (en) * | 2022-01-12 | 2022-05-03 | 上海大学 | MoS2Fluorescence quantum dot with @ organic polymer shell structure and preparation method thereof |
| CN114426842B (en) * | 2022-01-12 | 2024-05-14 | 上海大学 | MoS (MoS)2Fluorescent quantum dot of@organic polymer shell structure and preparation method thereof |
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