CN110358064B - Preparation and test method of non-conjugated system emission fluorescent polymer - Google Patents
Preparation and test method of non-conjugated system emission fluorescent polymer Download PDFInfo
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Abstract
The invention discloses a preparation and test method of a non-conjugated system emission fluorescent polymer, which comprises the steps of weighing anhydrous glucose, lactide and stannous octoate Sn (Oct)2Adding toluene to a flask for dissolving, refluxing for 24 hours at 140 ℃ by water separation, concentrating a reaction solution, dripping the reaction solution into anhydrous ether for recrystallization, filtering, and drying the obtained solid for 12 hours in vacuum to obtain a brown solid; the prepared brown solid was dissolved in DMF solution to prepare a polymer solution, and the fluorescence spectrum was measured from low concentration to high concentration. The invention has the beneficial effects that: glucose is used as a polyhydroxy center, a series of polylactic acids with different molecular weights are synthesized by utilizing different feed ratios, the fluorescence change under different concentrations is tested, the emission wavelength shows regular change along with the movement of the excitation wavelength, a new testing method is provided for the detection of the ideal green high polymer material polylactic acid, and particularly, the testing mode of the nano aggregate with the polylactic acid as a block in the high polymer self-assembly drug-loading system is greatly expanded.
Description
Technical Field
The invention relates to the technical field of fluorescent polymer preparation, in particular to a preparation and test method of a non-conjugated system emission fluorescent polymer.
Background
Organic light emitting materials are receiving much attention due to unique photophysical properties and wide application such as photoelectric devices, chemical or biological probes and bio-imaging fields. In addition to conventional conjugated organic compounds, there are also some unconventional luminescent materials without classical chromophores such as aromatic rings. Among these materials, non-conjugated polymers with flexible chain segments and adjustable structures have attracted great interest because of their important fundamental significance and broad application prospects. These polymers typically contain electron rich heteroatoms such as N, O, S and the like. Compared with the traditional conjugated materials, the conjugated material has the advantages of simple preparation, environmental friendliness, good biocompatibility and the like, and is very suitable for biomedical application.
Polylactic acid as an ideal green polymer material has excellent comprehensive performance, no pollution in the production process, good biocompatibility and biodegradability, the terminal degradation products mainly comprise water and carbon dioxide, and the intermediate product lactic acid is also a normal sugar metabolite in vivo and has biological safety. Has been widely applied to various fields such as biomedicine, electronics, daily disposable products and the like.
In general, longer excitation and emission wavelengths make it easier for light to penetrate thicker samples, which facilitates in vivo experiments. At the same time, longer excitation wavelengths have less detrimental effect on cells and tissues in the biological sample. However, non-conventional luminescent materials typically emit in the blue and green regions. Although they generally show photoluminescence in connection with excitation, few effective yellow and red emissions are found. Therefore, synthesizing a non-traditional fluorescent material capable of emitting red light under certain conditions is crucial to exploring the fluorescence emission law of a fluorescence mechanism.
Disclosure of Invention
The invention aims to overcome the technical defects and provides a preparation and test method of a non-conjugated system fluorescent emission polymer.
In order to achieve the purpose of the invention, the invention adopts the technical scheme that: a preparation and test method of a non-conjugated system emission fluorescent polymer, which takes polyhydroxy compound glucose as a center and connects polyester-based polymer polylactic acid, organic solutions of a series of polymers have characteristic fluorescence peaks, and the polylactic acid is synthesized by taking glucose as the center of polyhydroxy, and the specific preparation method comprises the following steps: weighing anhydrous glucose, lactide, stannous octoate Sn (Oct)2Adding toluene to a flask for dissolving, carrying out water-sharing reflux at 140 ℃ for 24 hours, concentrating the reaction solution, and drippingRecrystallizing in anhydrous ether, filtering, and vacuum drying the obtained solid for 12 hours to obtain brown solid;
the fluorescence test method is as follows: the prepared brown solid is dissolved in DMF solution, polymer solution with various concentrations is prepared by gradual dilution, and a fluorescence spectrum is tested from low concentration to high concentration, wherein an incidence slit is 1.75nm, an emergence slit is 1.25nm, an excitation wavelength is 380nm, and emission wavelengths are 425nm and 485 nm.
Further, the anhydrous glucose, the lactide, the stannous octoate Sn (Oct)2The feeding ratio is (1:70:0.35) or (1:120:0.6) or (1:180:0.9) or (1:240:1.2) or (1:300: 1.5).
Further, the fluorescence excitation wavelength is 380nm, the emission wavelength is 425nm and 485nm, and when the fluorescence intensity reaches the peak value, the fluorescence emission intensity decreases and the wavelength red shifts with the increase of the concentration.
Further, when the excitation wavelength is shifted from 400nm to 600nm and the emission wavelength is shifted from 500nm to 660nm, a red shift occurs and the fluorescence intensity decreases with the red shift of the excitation wavelength, and the fluorescence emission shifts from the green wavelength band to the red wavelength band.
The invention has the beneficial effects that: glucose is used as a polyhydroxy center, a series of polylactic acids with different molecular weights are synthesized by using different feed ratios, a fluorescence spectrophotometer is used for testing the fluorescence change under different concentrations, the emission wavelength shows regular change along with the movement of the excitation wavelength, a new testing method is provided for the detection of the ideal green high polymer material polylactic acid, and particularly, the testing mode of the high polymer self-assembly drug-loading system for the nano-aggregate with the polylactic acid as a block is greatly expanded.
Drawings
FIG. 1 is a polylactic acid nuclear magnetic diagram;
FIG. 2 is a dilution fluorescence spectrum of a product obtained by adding anhydrous glucose, lactide and Sn (Oct)2 at a feeding ratio of 1:70:0.35 at a concentration of lambda ex-380 nm;
FIG. 3 shows anhydrous glucose, lactide, Sn (Oct)2The feeding ratio is 1:70:0.35, and the obtained product has an increasing fluorescence spectrum at the excitation wavelength of 6 mg/mL;
FIG. 4 is a dilution fluorescence spectrum of a product obtained by adding anhydrous glucose, lactide and Sn (Oct)2 at a feeding ratio of 1:120:0.6 at a concentration of lambda ex-380 nm;
FIG. 5 shows anhydrous glucose, lactide, Sn (Oct)2The fluorescence spectrum of the obtained product is increased at the excitation wavelength of 10mg/mL with the feeding ratio of 1:120: 0.6.
Fig. 6 is a dilution fluorescence spectrum of a product obtained by adding anhydrous glucose, lactide and Sn (Oct)2 at a feeding ratio of 1:180:0.9 at a concentration of lambda ex-380 nm;
FIG. 7 shows anhydrous glucose, lactide, Sn (Oct)2The feeding ratio is 1:180:0.9, and the obtained product has an increasing fluorescence spectrum at the excitation wavelength of 10 mg/mL;
fig. 8 is a dilution fluorescence spectrum of the product obtained by using anhydrous glucose, lactide and Sn (Oct)2 in a feeding ratio of 1:240:1.2 at a concentration of lambda ex-380 nm;
FIG. 9 shows anhydrous glucose, lactide, Sn (Oct)2The fluorescence spectrum of the obtained product at the excitation wavelength of 20mg/mL is increased at the feeding ratio of 1:240: 1.2.
Fig. 10 is a dilution fluorescence spectrum of the product obtained by adding anhydrous glucose, lactide and Sn (Oct)2 at a feeding ratio of 1:300:1.5 at a concentration of lambda ex-380 nm;
FIG. 11 shows anhydrous glucose, lactide, Sn (Oct)2The fluorescence spectrum of the obtained product at the excitation wavelength of 20mg/mL is increased when the feeding ratio is 1:300: 1.5.
Detailed Description
In order to make the content of the present invention more clearly understood, the technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the drawings in the embodiments of the present invention.
Example 1
Preparing polylactic acid capable of emitting fluorescence: anhydrous glucose, lactide, stannous octoate Sn (Oct)2The molar ratio is 1:70: 0.35; weighing anhydrous glucose, lactide and stannous octoate Sn (Oct) according to the molar ratio2A small amount of toluene was added to the flask to dissolve the mixture, and the mixture was refluxed with water at 140 ℃ for 24 hours. After the reaction solution is concentrated, the reaction solution is dripped into anhydrous ether for recrystallization and filtration, the obtained solid is dried for 12 hours in vacuum, and a brown solid is obtained, wherein the nuclear magnetic characterization is shown in figure 1.
Dissolving 0.1g of prepared brown solid in 5mL of mixed solution of DMMF (liquid chromatography/liquid chromatography) at a concentration of 10mg/mL, gradually diluting to prepare polymer solutions with various concentrations, testing a fluorescence spectrum from low concentration to high concentration, wherein an incidence slit is 1.75nm, an emergence slit is 1.25nm, an excitation wavelength is 380nm, emission wavelengths are 425nm and 485nm, determining that the maximum concentration of fluorescence intensity is 6mg/mL, and under the concentration, the emission wavelength is red-shifted and the fluorescence intensity is reduced along with the increase of the excitation wavelength, specifically referring to fig. 2 and fig. 3.
Example 2
Preparation of polylactic acid capable of emitting fluorescence, anhydrous glucose, lactide, stannous octoate Sn (Oct)2The molar ratio is 1:120:0.6, and anhydrous glucose, lactide and stannous octoate Sn (Oct) are weighed according to the molar ratio2A small amount of toluene was added to the flask to dissolve the mixture, and the mixture was refluxed with water at 140 ℃ for 24 hours. After the reaction solution is concentrated, the reaction solution is dripped into anhydrous ether for recrystallization and filtration, and the obtained solid is dried for 12 hours in vacuum to obtain brown solid.
Dissolving 0.3g of prepared brown solid in 5mL of mixed solution of DMMF (liquid chromatography/liquid chromatography) at a concentration of 60mg/mL, gradually diluting to prepare polymer solutions with various concentrations, testing a fluorescence spectrum from low concentration to high concentration, wherein an incidence slit is 1.75nm, an emergence slit is 1.25nm, an excitation wavelength is 380nm, emission wavelengths are 425nm and 485nm, determining that the maximum concentration of fluorescence intensity is 10mg/mL, and under the concentration, the emission wavelength is red-shifted and the fluorescence intensity is reduced along with the increase of the excitation wavelength, specifically referring to fig. 4 and 5.
Example 3
Preparation of polylactic acid capable of emitting fluorescence, anhydrous glucose, lactide, stannous octoate Sn (Oct)2The molar ratio is 1:180:0.9, and anhydrous glucose, lactide and stannous octoate Sn (Oct) are weighed according to the molar ratio2A small amount of toluene was added to the flask to dissolve the mixture, and the mixture was refluxed with water at 140 ℃ for 24 hours. After the reaction solution is concentrated, the reaction solution is dripped into anhydrous ether for recrystallization and filtration, and the obtained solid is dried for 12 hours in vacuum to obtain brown solid.
Dissolving 0.3g of prepared brown solid in 5mL of mixed solution of DMMF (liquid chromatography/liquid chromatography) at a concentration of 60mg/mL, gradually diluting to prepare polymer solutions with various concentrations, testing a fluorescence spectrum from low concentration to high concentration, wherein an incidence slit is 1.75nm, an emergence slit is 1.25nm, an excitation wavelength is 380nm, emission wavelengths are 425nm and 485nm, determining that the maximum concentration of fluorescence intensity is 10mg/mL, and under the concentration, the emission wavelength is red-shifted and the fluorescence intensity is reduced along with the increase of the excitation wavelength, specifically referring to fig. 6 and 7.
Example 4
Preparation of polylactic acid capable of emitting fluorescence, anhydrous glucose, lactide, stannous octoate Sn (Oct)2The molar ratio is 1:240:1.2, and anhydrous glucose, lactide and stannous octoate Sn (Oct) are weighed according to the molar ratio2A small amount of toluene was added to the flask to dissolve the mixture, and the mixture was refluxed with water at 140 ℃ for 24 hours. After the reaction solution is concentrated, the reaction solution is dripped into anhydrous ether for recrystallization and filtration, and the obtained solid is dried for 12 hours in vacuum to obtain brown solid.
Dissolving 0.5g of prepared brown solid in 5mL of DMMF solution, wherein the concentration is 100mg/mL, gradually diluting to prepare polymer solutions with various concentrations, testing a fluorescence spectrum from low concentration to high concentration, wherein an incidence slit is 1.75nm, an emergence slit is 1.25nm, an excitation wavelength is 380nm, emission wavelengths are 425nm and 485nm, determining that the maximum concentration of fluorescence intensity is 20mg/mL, and under the concentration, the emission wavelength is red-shifted and the fluorescence intensity is reduced along with the increase of the excitation wavelength, specifically referring to fig. 8 and 9.
Example 5
Preparation of polylactic acid capable of emitting fluorescence, anhydrous glucose, lactide, stannous octoate Sn (Oct)2The molar ratio is 1:300:1.5, and anhydrous glucose, lactide and stannous octoate Sn (Oct) are weighed according to the molar ratio2A small amount of toluene was added to the flask to dissolve the mixture, and the mixture was refluxed with water at 140 ℃ for 24 hours. After the reaction solution is concentrated, the reaction solution is dripped into anhydrous ether for recrystallization and filtration, and the obtained solid is dried for 12 hours in vacuum to obtain brown solid.
Dissolving 0.5g of prepared brown solid in 5mL of DMMF solution, wherein the concentration is 100mg/mL, gradually diluting to prepare polymer solutions with various concentrations, testing a fluorescence spectrum from low concentration to high concentration, wherein an incidence slit is 1.75nm, an emergence slit is 1.25nm, an excitation wavelength is 380nm, emission wavelengths are 425nm and 485nm, determining that the maximum concentration of fluorescence intensity is 20mg/mL, and under the concentration, the emission wavelength is red-shifted and the fluorescence intensity is reduced along with the increase of the excitation wavelength, specifically referring to fig. 10 and fig. 11.
The mechanism of the invention is as follows: when the polymer is excited in a dilute solution, the emission energy is consumed by intramolecular movement, resulting in weak or even no fluorescence. As the concentration increases, the polymer chains approach each other and entangle with each other, greatly increasing the aggregation of carbonyl groups. The lone pair electrons and the pi electrons in the cluster interact and overlap to generate space conjugation, and the fluorescence intensity is greatly enhanced. When the concentration is further increased, the molecular chain is gradually fixed, carbonyl aggregation cannot effectively occur, and the fluorescence intensity gradually decreases. As a result, the fluorescence intensity tends to increase and decrease as the concentration of the polyester solution increases. Due to the multi-arm polylactic acid structure, the generation of space conjugation depends on the aggregation between terminal carbonyl groups of molecules, and when the molecular weight of a polymer is smaller, the number of molecules is more under the same mass concentration, so that the mass concentration required for reaching the same fluorescence intensity is smaller.
The present invention and the embodiments thereof have been described above, but the description is not limited to the embodiments, but only one of the embodiments of the present invention, and the actual embodiments are not limited thereto. In summary, those skilled in the art should appreciate that they can readily use the disclosed conception and specific embodiments as a basis for designing or modifying other structures for carrying out the same purposes of the present invention without departing from the spirit and scope of the invention as defined by the appended claims.
Claims (4)
1. A preparation method of a non-conjugated system emission fluorescent polymer is characterized in that: the preparation method comprises the following steps of taking glucose as a center of a polyhydroxy compound, connecting polylactic acid of a polyester-based polymer, synthesizing the polylactic acid by taking the glucose as the center of the polyhydroxy compound, wherein organic solutions of a series of polymers have characteristic fluorescence peaks, and the preparation method comprises the following steps:
weighing anhydrous glucose, lactide, stannous octoate Sn (Oct)2 Adding toluene to a flask for dissolving, refluxing for 24 hours at 140 ℃ by water separation, concentrating a reaction solution, dripping the reaction solution into anhydrous ether for recrystallization, filtering, and drying the obtained solid for 12 hours in vacuum to obtain a brown solid;
the fluorescence test method is as follows: the prepared brown solid is dissolved in DMF solution, polymer solution with various concentrations is prepared by gradual dilution, and a fluorescence spectrum is tested from low concentration to high concentration, wherein an incidence slit is 1.75nm, an emergence slit is 1.25nm, an excitation wavelength is 380nm, and emission wavelengths are 425nm and 485 nm.
2. The method for preparing a non-conjugated system emission fluorescent polymer according to claim 1, wherein: the anhydrous glucose, the lactide and the stannous octoate Sn (Oct)2The feeding ratio is 1:70:0.35 or 1:120:0.6 or 1:180:0.9 or 1:240:1.2 or 1:300: 1.5.
3. The method for preparing a non-conjugated system emission fluorescent polymer according to claim 1, wherein: the fluorescence excitation wavelength is 380nm, the emission wavelength is 425nm and 485nm, and when the fluorescence intensity reaches the peak value, the fluorescence emission intensity is reduced and the wavelength is red-shifted along with the increase of the concentration.
4. The method for preparing a non-conjugated system emission fluorescent polymer according to claim 1, wherein: the excitation wavelength is shifted from 400nm to 600nm, the emission wavelength is shifted from 500nm to 660nm, red shift occurs and the fluorescence intensity decreases with the red shift of the excitation wavelength, and the fluorescence emission is shifted from the green band to the red band.
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