CN110283584B - PFPV semiconductor polymer quantum dot fluorescent probe and preparation method and application thereof - Google Patents
PFPV semiconductor polymer quantum dot fluorescent probe and preparation method and application thereof Download PDFInfo
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Abstract
The invention discloses a PFPV semiconductor polymer quantum dot fluorescent probe and a preparation method thereof, wherein the preparation method comprises the following steps: 1) Dissolving polymer PFPV in a good solvent to prepare a PFPV good solvent precursor solution, transferring the PFPV good solvent precursor solution to a first injector, and placing a poor solvent in a second injector; 2) Respectively placing a first injector and a second injector at two inlets of a current-limiting collision mixer, and placing a beaker filled with a poor solvent at an outlet of the current-limiting collision mixer; 3) Meanwhile, the first injector and the second injector are pushed so that the liquids in the first injector and the second injector are collided face to face in a closed flow path of the current-limiting collision mixer and are mixed violently, then the mixed liquid flows into a beaker filled with a poor solvent in a stirring state, and finally the colloidal solution in the beaker is filtered to obtain a filtrate. The fluorescent probe has the characteristics of small size, high brightness, good stability, no toxicity and the like.
Description
Technical Field
The invention relates to a nano fluorescent probe, in particular to a PFPV semiconductor polymer quantum dot fluorescent probe and a preparation method thereof.
Background
Semiconductor polymers are polymers whose main chain is composed of single bonds and double or triple bonds alternately, have photoelectric properties of wide bandgap semiconductors, and are widely used in the fields of various electronic devices such as light emitting diodes, sensors, tissue engineering and the like (anal. Chem.,2017,89, 42-56). The structural characteristics of semiconductor polymers determine that the materials not only have good luminescence properties such as high brightness and no light flicker, but also have the advantages of large molar absorptivity, high fluorescence quantum efficiency, large Stokes shift, good stability and the like, and are very suitable for being used as new fluorescent probe materials (chem. Soc. Rev.,2013,42, 6620-6633). In 2005, mcNeill topic group of Clemson university in usa reported for the first time that a polymer quantum dot prepared from a semiconductor polymer poly [ 2-methoxy-5- (2-ethylhexyloxy) -1, 4-phenylenevinylene ] (MEH-PPV) and found that it has both properties of conjugated polymer and nanoparticle (j.phys.chem.b., 2005,109, 8543-8546), and thus, this novel nano fluorescent particle has been receiving attention due to its excellent fluorescence property, and at the same time, this discovery also opened the way of research on fluorescent conjugated polymer nanoparticles.
Currently, the preparation method of conjugated polymer nanoparticles can be broadly divided into two methods, i.e., direct polymerization (prepared from low molecular weight monomers) and post-polymerization (prepared from high molecular weight monomers). Typical methods are mainly post-polymerization methods, which can be classified into micro-emulsion methods and co-precipitation methods. This process firstly dissolves the semiconductor polymer in the organic phase as a mother liquor and secondly disperses it with water (water is preferred since the material is ultimately used in the biological field)
Specifically, the microemulsion method: firstly, dissolving a polymer in an organic phase, secondly, adding a certain amount of surfactant into water for dispersing the polymer, then forming emulsified droplets by the hydrophobic polymer dissolved in the organic phase under the action of the surfactant, and finally removing the organic phase to obtain the nano particles stably dispersed in the water. The method has the defect that the used surfactant has high biological toxicity, so that the application of the semiconductor polymer nano particles prepared by the microemulsion method in the aspects of biological analysis and sensing is limited. A coprecipitation method: firstly, dissolving a polymer in an organic phase to prepare a mother solution, secondly, quickly injecting the polymer dissolved in the organic phase into water under the action of ultrasound, continuing to perform ultrasound for 3-5min, and finally removing the organic phase to obtain the nano particles. In the coprecipitation method, although the method has the advantages of simplicity, rapidness and the like, the method also has the defects of dilute concentration of prepared nanoparticles, poor uniformity of size distribution, difficult controllable synthesis and the like. Therefore, the preparation of the semiconductor polymer fluorescent nano-particles with uniform size distribution and excellent performance has very important significance for exploring the application of the nano-materials in fluorescence sensing and biological imaging.
Disclosure of Invention
The invention aims to provide a PFPV semiconductor polymer quantum dot fluorescent probe and a preparation method thereof.
In order to achieve the above object, the present invention provides a method for preparing a PFPV semiconductor polymer quantum dot fluorescent probe, comprising:
1) Dissolving polymer PFPV in a good solvent to prepare a PFPV good solvent precursor solution, transferring the PFPV good solvent precursor solution to a first injector, and placing a poor solvent in a second injector;
2) Respectively placing a first injector and a second injector at two inlets of a current-limiting collision mixer, and placing a beaker filled with a poor solvent at an outlet of the current-limiting collision mixer;
3) Simultaneously pushing the first injector and the second injector to enable the liquids in the first injector and the second injector to impact and mix violently in a closed flow path of the current-limiting collision mixer, enabling the mixed liquids to flow into a beaker containing a poor solvent in a stirring state, and finally filtering colloidal solution in the beaker to obtain filtrate so as to obtain the PFPV semiconductor polymer quantum dot fluorescent probe;
wherein the volumes of the liquids contained in the first syringe and the second syringe are the same, and the polymer PFPV is poly [ {9, 9-dioctyl-2, 7-divinylidene-fluorenylidene } -alt-co- { 2-methoxy-5- (2-ethylhexyloxy) -1, 4-phenylene } ].
The invention also provides a PFPV semiconductor polymer quantum dot fluorescent probe, which is prepared by the preparation method.
The invention further provides an application of the PFPV semiconductor polymer quantum dot fluorescent probe in fluorescence sensing and fluorescence imaging.
The invention takes semiconductor polymer PFPV as a precursor, and prepares the PFPV semiconductor polymer quantum dot fluorescent probe by a limited-area blending precipitation method with the help of a good solvent and a poor solvent. The zone-limited blending precipitation method is a new technology for preparing polymer nano particles by fast one-step self-assembly, and the polymer is spontaneously assembled into nano particles with specific functions under certain conditions and environments mainly by depending on the physical and chemical properties of the components. The invention dissolves hydrophobic PFPV in good solvent which can be mutually dissolved with poor solvent to prepare precursor solution, the precursor solution and the poor solvent are simultaneously and rapidly injected into a specific closed flow path of a current-limiting collision mixer, the PFPV instantly achieves supersaturation in the poor solvent to generate precipitation due to the generated rapid vortex (the Reynolds index is 1500-4500, preferably 3450-3550), and the PFPV spontaneously assembles spherical polymer quantum dot nano particles in the rapid precipitation process. The method can obtain the nano particles with adjustable appearance and size and narrower particle size distribution.
Compared with the prior art, the invention has the advantages that:
a) The invention has the characteristics of simple instrument and equipment, high preparation speed, uniform prepared nano particles, narrow particle size distribution and the like, and the preparation method is simple, controllable and easy to popularize.
B) The PFPV semiconductor polymer quantum dot fluorescent probe prepared by the invention has the characteristics of small particle size, high brightness, good light stability, high stability and the like, and is very suitable for the fields of fluorescence sensing and fluorescence imaging.
Additional features and advantages of the invention will be set forth in the detailed description which follows.
Drawings
The accompanying drawings, which are included to provide a further understanding of the invention and are incorporated in and constitute a part of this specification, illustrate embodiments of the invention and together with the description serve to explain the principles of the invention and not to limit the invention. In the drawings:
FIG. 1 is an absorption spectrum diagram of the fluorescent probe of the polymer quantum dot obtained in example 1;
FIG. 2 is a fluorescence emission spectrum of the fluorescent probe of the polymer quantum dot obtained in example 1;
FIG. 3 is a Transmission Electron Microscope (TEM) photograph of the polymer quantum dot fluorescent probe obtained in example 1;
FIG. 4 is a dynamic light scattering spectrum of the fluorescent probe of the polymer quantum dot obtained in example 1;
FIG. 5 is a fluorescent probe diagram of the polymer quantum dot fluorescent probe obtained in example 1.
Detailed Description
The following describes the embodiments of the present invention in detail. It should be understood that the detailed description and specific examples, while indicating the preferred embodiment of the invention, are given by way of illustration and explanation only, not limitation.
The endpoints of the ranges and any values disclosed herein are not limited to the precise range or value, and such ranges or values should be understood to encompass values close to those ranges or values. For ranges of values, between the endpoints of each of the ranges and the individual points, and between the individual points may be combined with each other to give one or more new ranges of values, and these ranges of values should be considered as specifically disclosed herein.
The invention provides a preparation method of a PFPV semiconductor polymer quantum dot fluorescent probe, which comprises the following steps:
1) Dissolving a polymer PFPV in a good solvent to prepare a PFPV good solvent precursor solution, transferring the PFPV good solvent precursor solution into a first injector, and placing a poor solvent into a second injector;
2) Respectively placing a first injector and a second injector at two inlets of a current-limiting collision mixer, and placing a beaker filled with a poor solvent at an outlet of the current-limiting collision mixer;
3) Simultaneously pushing the first injector and the second injector to enable the liquids in the first injector and the second injector to impact and mix violently in a closed flow path of the current-limiting collision mixer, enabling the mixed liquids to flow into a beaker containing a poor solvent in a stirring state, and finally filtering colloidal solution in the beaker to obtain filtrate so as to obtain the PFPV semiconductor polymer quantum dot fluorescent probe;
wherein the volumes of the liquids contained in the first syringe and the second syringe are the same, and the polymer PFPV is poly [ {9, 9-dioctyl-2, 7-bisvinylene-fluorenylidene } -alt-co- { 2-methoxy-5- (2-ethylhexyloxy) -1, 4-phenylene } ]; the flow-limiting impingement mixer was prepared from FIGS. 2 and 3 of the reference "Han, J., et al. (2012)," A simple defined impact mixers for flash nanoprecitations, "Journal of Pharmaceutical Sciences 101 (10): 4018-4023".
In the above preparation method, the kinds of the good solvent and the poor solvent can be selected in a wide range, but in order to further control the morphology, the uniformity of the nanoparticles, and the particle size distribution of the PFPV semiconductor polymer quantum dot fluorescent probe, preferably, the good solvent is at least one of tetrahydrofuran, acetonitrile, dimethylsulfoxide, N-dimethylformamide, dioxane; more preferably tetrahydrofuran; the poor solvent is water.
In the above preparation method, the volume ratio of the liquids in the first syringe, the second syringe and the beaker can be selected in a wide range, but in order to further control the morphology, the uniformity and the particle size distribution of the nanoparticles of the PFPV semiconductor polymer quantum dot fluorescent probe, the volume ratio of the liquids in the first syringe and the beaker is preferably 1:1-15, preferably 1:6-8.
In the above preparation method, the concentration of the PFPV good solvent precursor solution can be selected in a wide range, but in order to further control the morphology, nanoparticle uniformity and particle size distribution of the PFPV semiconductor polymer quantum dot fluorescent probe, the concentration of PFPV in the PFPV good solvent precursor solution is preferably 15-1000ug/mL.
In the above preparation method, the flow rates of the liquids in the first syringe and the second syringe in the closed flow path can be selected in a wide range, but in order to further control the morphology, the uniformity of the nanoparticles and the particle size distribution of the PFPV semiconductor polymer quantum dot fluorescent probe, the flow rate ratio of the liquids in the first syringe and the second syringe in the closed flow path is preferably 1:0.95-1.05; more preferably, the flow rates of the liquids in the first syringe and the second syringe in the closed channel are each independently 0.6 to 5ml/s.
In the above production method, the filtration manner can be selected within a wide range, but in order to further improve the filtration effect, it is preferable that the filtration is performed using an aqueous phase needle filter, and more preferably, the pore diameter of the aqueous phase needle filter is 0.2 to 0.3. Mu.m.
The invention also provides a PFPV semiconductor polymer quantum dot fluorescent probe, which is prepared by the preparation method.
In the PFPV semiconductor polymer quantum dot fluorescent probe, in order to further improve the fluorescent effect of the PFPV semiconductor polymer quantum dot fluorescent probe, preferably, the PFPV semiconductor polymer quantum dot fluorescent probe has a spherical center and an average particle diameter of 4.6-5nm; more preferably, the PFPV semiconductor polymer quantum dot fluorescent probe has a maximum ultraviolet absorption wavelength of 455-460nm and a maximum fluorescence emission wavelength of 510-520nm.
The invention further provides application of the PFPV semiconductor polymer quantum dot fluorescent probe in fluorescence sensing and fluorescence imaging.
The present invention will be described in detail below by way of examples. In the following examples, the flow-limiting impingement mixer was prepared from references (Han, J., et al. (2012) 'A simple defined impregnation mixer for flash nanopropractionation.' Journal of Pharmaceutical Sciences 101 (10): 4018-4023) FIGS. 2 and 3; PFPV is commercially available from the company SiAnborate.
Example 1
A) Dissolving 3mg of polymer PFPV in 3mL of tetrahydrofuran to prepare 1mg/mL of PFPV good solvent precursor solution, taking a certain amount of precursor solution to dilute the precursor solution to 20 mu g/mL, taking 1mL of the precursor solution after dilution, transferring the precursor solution into an injector, and taking another injector to load 1mL of poor solvent water with the same volume.
B) Placing the two injectors at two inlets of a flow-limiting collision mixer respectively; a beaker containing 7mL of poor solvent water was placed at the outlet.
C) Both syringes were pushed simultaneously with the same force to force the solution at a rate of 1.2ml/s (the ratio of the rate of fluid flow out of both syringes was close to 1: 1) The mixed liquid flows into a beaker filled with 7mL of poor solvent under stirring (the stirring speed is 450-1200 r/min) through head-on collision and vigorous mixing in a closed flow path of a current-limiting collision mixer (a rapid vortex with a Reynolds index of 3500 is generated); and (3) stirring for 3-6min after the liquid in the two injectors flows out, filtering the colloidal solution obtained in the beaker by using a water phase needle type filter (the pore diameter is 0.22 mu m) after the reaction is finished, and obtaining filtrate, namely the PFPV semiconductor polymer quantum dot fluorescent probe.
Example 2
The procedure is as in example 1, except that the concentration of the precursor solution in the syringe is 200. Mu.g/mL.
Example 3
The procedure is as in example 1, except that the concentration of the precursor solution in the syringe is 1mg/mL.
Example 4
The procedure was as in example 1, except that the volume of the poor solvent in the beaker was 15mL.
Example 5
The procedure was followed as in example 1, except that the volume of the poor solvent in the beaker was 1mL.
Example 6
The procedure was as in example 1, except that the liquid in the syringe was discharged at a rate of 5ml/s.
Example 7
The procedure is as in example 1, except that the rate of liquid outflow from the syringe is 0.6ml/s.
Example 8
The procedure is as in example 1, except that the good solvent is acetonitrile.
Example 9
The procedure is as in example 1, except that the good solvent is dioxane.
Test example 1
1) The product of example 1 was subjected to ultraviolet absorption spectroscopy by means of an ultraviolet absorption spectrometer of Hitachi, japan, model No. U-3900, and the result of the inspection is shown in FIG. 1, from which it is seen that the maximum ultraviolet absorption wavelength is 457nm.
2) The fluorescence emission spectrum of the product of example 1 was detected by a fluorescence spectrometer of the model LUMINA of Saimer Feishell science and technology, and the detection result is shown in FIG. 2, from which it can be seen that the maximum fluorescence emission wavelength was 515nm.
3) The product of example 1 was examined by transmission electron microscopy using a transmission electron microscope of type HT-7700, hitachi, japan, and the examination result is shown in FIG. 3, from which it is understood that the product had a spherical shape with good dispersibility and an average particle diameter of about 4.8 nm.
4) Dynamic light scattering spectrum detection is carried out on the product of the example 1 by a Germany ALV/Laser type CCTS-8F Laser light scattering spectrometer, the detection result is shown in figure 4, and the particle size distribution range of the synthesized Pdots is 3.6-9.6nm.
5) The PFPV semiconductor polymer quantum dot fluorescent probe prepared in example 1 with the concentration of 20g/mL is incubated for 24h in HeLa cells, and observed by a confocal laser scanning microscope, the observation result is shown in FIG. 5, wherein the upper left graph shows that Pdots with green fluorescence are distributed in cytoplasm, the upper right graph shows that blue fluorescence is stained cell nucleus, the lower left graph shows that cells observed under a dark field, and the lower right graph shows that cells observed under a bright field, and it can be known that Pdots enter cells, can be attached to the periphery of cell nucleus and can not affect the normal physiological activity of the cells.
The products of examples 2 to 9 were examined in the same manner as described above, and the examination results were substantially identical to those of the product of example 1.
The preferred embodiments of the present invention have been described in detail, however, the present invention is not limited to the specific details of the above embodiments, and various simple modifications may be made to the technical solution of the present invention within the technical idea of the present invention, and these simple modifications are within the protective scope of the present invention.
It should be noted that the various technical features described in the above embodiments can be combined in any suitable manner without contradiction, and the invention is not described in any way for the possible combinations in order to avoid unnecessary repetition.
In addition, any combination of the various embodiments of the present invention is also possible, and the same should be considered as the disclosure of the present invention as long as it does not depart from the spirit of the present invention.
Claims (10)
1. A preparation method of a PFPV semiconductor polymer quantum dot fluorescent probe is characterized by comprising the following steps:
1) Dissolving a polymer PFPV in a good solvent to prepare a PFPV good solvent precursor solution, transferring the PFPV good solvent precursor solution into a first injector, and placing a poor solvent into a second injector;
2) Respectively placing the first injector and the second injector at two inlets of a current-limiting collision mixer, and placing a beaker filled with a poor solvent at an outlet of the current-limiting collision mixer;
3) Simultaneously pushing the first injector and the second injector to enable the liquids in the first injector and the second injector to impact in a head-on manner in a closed flow path of the current-limiting collision mixer and to be mixed vigorously, enabling the mixed liquids to flow into the beaker containing the poor solvent in a stirring state, and finally filtering the colloidal solution in the beaker to obtain a filtrate so as to obtain the PFPV semiconductor polymer quantum dot fluorescent probe;
wherein the first syringe and the second syringe contain the same volume of liquid, and the polymer PFPV is poly [ {9, 9-dioctyl-2, 7-divinyl-fluorenylidene } -alt-co- { 2-methoxy-5- (2-ethylhexyloxy) -1, 4-phenylene } ];
wherein the good solvent is tetrahydrofuran;
wherein the poor solvent is water;
wherein the volume ratio of the liquid in the first injector and the liquid in the beaker is 1:6-8.
2. The preparation method of claim 1, wherein the concentration of PFPV in the PFPV good solvent precursor solution is 15-1000ug/mL.
3. The production method according to claim 1, wherein a flow rate ratio of the liquid in the first syringe to the liquid in the second syringe in the closed channel is 1:0.95-1.05.
4. The production method according to claim 1, wherein the flow rates of the liquids in the first syringe and the second syringe in the closed channel are each independently 0.6 to 5ml/s.
5. The production method according to claim 1, wherein the filtration is performed using an aqueous phase needle filter.
6. The production method according to claim 5, wherein the pore size of the aqueous phase needle filter is 0.2 to 0.3 μm.
7. A PFPV semiconductor polymer quantum dot fluorescent probe, characterized in that, the PFPV semiconductor polymer quantum dot fluorescent probe is prepared by the preparation method of any one of claims 1 to 6.
8. The PFPV semiconductor polymer quantum dot fluorescent probe of claim 7, wherein the PFPV semiconductor polymer quantum dot fluorescent probe is a spherical type with an average particle size of 4.6-5 nm.
9. The PFPV semiconductor polymer quantum dot fluorescent probe of claim 7, wherein the maximum ultraviolet absorption wavelength of the PFPV semiconductor polymer quantum dot fluorescent probe is 455-460nm and the maximum fluorescence emission wavelength is 510-520nm.
10. Use of the PFPV semiconducting polymer quantum dot fluorescent probe of any of claims 7-9 for fluorescence sensing and fluorescence imaging.
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| CN109529059A (en) * | 2018-12-26 | 2019-03-29 | 中南大学 | A kind of fluorescence-magnetic resonance bimodal quantum dot and its methods for making and using same |
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| CN109529059A (en) * | 2018-12-26 | 2019-03-29 | 中南大学 | A kind of fluorescence-magnetic resonance bimodal quantum dot and its methods for making and using same |
Non-Patent Citations (3)
| Title |
|---|
| A simple confined impingement jets mixer for flash nanoprecipitation;Jing Han等;《Journal of Pharmaceutical Sciences》;20120706;第101卷(第10期);第4019页 * |
| Flash nanoprecipitation of polystyrene nanoparticles;Chuan Zhang等;《Soft Matter》;20111006;第8卷;第87页 * |
| Multicolor Conjugated Polymer Dots for Biological Fluorescence Imaging;Wu Changfeng等;《ACS Nano》;20081106;第2卷(第11期);第2417页 * |
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