CN113527729A - Aggregation-induced emission polymer film and macro preparation method thereof - Google Patents
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Abstract
The invention discloses an aggregation-induced emission polymer film and a macro preparation method thereof, wherein the macro preparation method comprises the following steps: dissolving a monomer A in an ionic liquid to obtain a monomer A solution; dissolving the monomer B in an organic solvent to obtain a monomer B solution; the monomer A is polyamine, polyalcohol and/or polyphenol with aggregation-induced luminescence property; the monomer B is polyacyl chloride and/or polyisocyanate; coating the monomer solution A on a substrate to form a liquid film with uniform thickness; placing the base material coated with the uniform liquid film in the monomer solution B, and carrying out interfacial polymerization reaction to generate an aggregation-induced emission polymer film on the surface of the base material; taking out the base material after the interfacial polymerization reaction, and immersing the base material into a detergent to automatically drop the generated aggregation-induced emission polymer film from the base material; and then drying and rolling the aggregation-induced emission polymer film. The macro preparation method has the advantages of mild reaction conditions, high efficiency and low cost.
Description
Technical Field
The invention relates to the technical field of functional film preparation, in particular to an aggregation-induced emission polymer film and a macro preparation method thereof.
Background
Luminescent materials are indispensable in modern society, have been widely used in illumination, display, sensing and the like, and are closely related to the lives of people. However, organic dyes always face the problem of quenching fluorescence in the solid state when preparing light emitting devices, which limits device performance. Improving the luminescence stability of the dye in the solid state is an important means for improving the performance of the luminescent material.
The fluorescence properties of aggregation-induced emission materials are different from those of conventional dyes. Aggregation-induced emission is a particular photophysical phenomenon discovered by the Tang Ben fai team, and the fluorescence intensity of materials with this property increases with increasing degree of molecular aggregation. Since the discovery of the beginning of the 21 st century, the aggregation-induced emission material effectively overcomes the problem that the luminous efficiency of the traditional organic light-emitting molecules is reduced along with the increase of the concentration, is more and more abundant in material types, and has wide application prospects in the fields of stimulus-responsive intelligent materials, flexible display materials, lighting materials, biological imaging and the like.
For example, chinese patent publication No. CN110849856A discloses an application of a salicylaldehyde hydrazone derivative having aggregation-induced emission performance in detection of nitrite ions, in which an aggregation-induced emission material is dissolved in a solvent and applied to detection of nitrite ions. Chinese patent publication No. CN110564093A discloses a controllable fluorescent ion gel with multiple stimulus responsiveness, the gel with aggregation-induced emission effect is prepared by the invention, the luminescent color of the gel can be controlled by changing the gel components, and the gel has application prospects in organic light-emitting diodes, chemical sensors, fluorescence detectors and other aspects.
In practical application, thin film organic luminescent materials are the most popular. However, there is no technique for forming a large-area thin film of aggregation-induced emission material. Generally, a spin coating method is adopted to prepare the aggregation-induced emission thin film, but the method has high requirements on equipment, higher cost and small product area, and is difficult to prepare a high molecular weight or crosslinked polymer thin film.
Based on this, it is necessary to develop a method for preparing a large-area aggregation-induced emission thin film material.
Interfacial polymerization is a polymerization reaction that occurs at the interface of two incompatible phases and is the main technique for industrially continuously producing a reverse osmosis membrane. The method has the advantages of low requirements on the purity of reaction monomers and the molar ratio of functional groups, high reaction rate, simpler process equipment and the like, and can be used for synthesizing materials such as polyamide, polyarylate, polycarbonate, polyurethane and the like.
Disclosure of Invention
The invention provides an aggregation-induced emission polymer film and a macro preparation method thereof.
The technical scheme of the invention is as follows:
a macro preparation method of an aggregation-induced emission polymer film comprises the following steps:
(1) dissolving a monomer A in an ionic liquid to obtain a monomer A solution; dissolving the monomer B in an organic solvent to obtain a monomer B solution;
the monomer A is polyamine, polyalcohol and/or polyphenol with aggregation-induced emission characteristics;
the monomer B is polyacyl chloride and/or polyisocyanate;
(2) coating the monomer solution A on a substrate to form a liquid film with uniform thickness;
(3) placing the base material coated with the uniform liquid film prepared in the step (2) in a monomer solution B for interfacial polymerization reaction to generate an aggregation-induced emission polymer film on the surface of the base material;
(4) taking out the base material after the interfacial polymerization reaction, and immersing the base material into a detergent to automatically drop the generated aggregation-induced emission polymer film from the base material; and then drying and rolling the aggregation-induced emission polymer film.
The above steps can be carried out at room temperature.
The macro preparation method of the invention uses aggregation-induced emission multifunctional molecules as reaction monomers to prepare the cross-linked polymer film, multifunctional amino or hydroxyl is connected to the periphery of the tetraphenylethylene structure, the reaction activity is improved while the special space structure of the aggregation-induced emission groups is maintained, and the cross-linked network structure generated by interfacial polymerization effectively limits the thermal motion of the tetraphenylethylene structure, so that the tetraphenylethylene structure returns to the ground state to emit fluorescence in a radiation transition mode under an excited state, thereby preparing the polymer film with aggregation-induced emission properties in a large area by a one-step method.
In the step (1), the monomer A is at least one of 1, 2-diphenyl-1, 2-bis (4-aminophenyl) ethylene, tetrakis (4-aminophenyl) ethylene, 1, 2-diphenyl-1, 2-bis (4-hydroxyphenyl) ethylene, tetrakis (4-hydroxyphenyl) ethylene, 1, 2-diphenyl-1, 2-bis (4-carboxyphenyl) ethylene and tetrakis (4-carboxyphenyl) ethylene.
The ionic liquid is at least one of 1-ethyl-3-methylimidazole tetrafluoroborate, 1-propyl-3-methylimidazole tetrafluoroborate, 1-butyl-3-methylimidazole tetrafluoroborate, 1-hexyl-3-methylimidazole tetrafluoroborate, 1-octyl-3-methylimidazole tetrafluoroborate, 1-ethyl-3-methylimidazole bistrifluoromethylsulfonyl imide salt, 1-butyl-3-methylimidazole bistrifluoromethylsulfonyl imide salt and bistrifluoromethylsulfonyl imide quaternary ammonium salt. Can be dissolved at room temperature, and can also be heated to accelerate the dissolution rate.
The viscosity of the ionic liquid is 50-500 mPas.
Preferably, the monomer A is at least one of 1, 2-diphenyl-1, 2-bis (4-aminophenyl) ethylene, tetrakis (4-aminophenyl) ethylene, 1, 2-diphenyl-1, 2-bis (4-hydroxyphenyl) ethylene and tetrakis (4-hydroxyphenyl) ethylene; the ionic liquid is at least one of 1-ethyl-3-methylimidazole tetrafluoroborate, 1-butyl-3-methylimidazole tetrafluoroborate, 1-hexyl-3-methylimidazole tetrafluoroborate and 1-butyl-3-methylimidazole bistrifluoromethylsulfonyl imide salt.
The monomer B is at least one of trimesoyl chloride, succinyl chloride, adipoyl chloride, suberoyl chloride, toluene diisocyanate, diphenylmethane diisocyanate, hexamethylene diisocyanate and naphthalene diisocyanate.
The organic solvent is at least one of n-hexane, n-octane, n-dodecane, isoparaffin, toluene, dichloroethane, trichloroethane and chloroform.
Preferably, the monomer B is at least one of succinyl chloride, suberoyl chloride, toluene diisocyanate and hexamethylene diisocyanate; the organic solvent is at least one of n-hexane, isoparaffin and toluene; most preferably, the organic solvent is n-hexane.
In addition to the two-phase solvent, the monomer concentration during interfacial polymerization to produce the film also determines the structural properties of the final film. The polymer which is rapidly generated in the early stage of the reaction under a proper monomer concentration ratio can effectively block the subsequent reaction, and finally the polymer with a certain thickness and a cross-linking structure is generated. If the monomer concentration is too high, the resulting film will be loose and thick, and if it is too low, a continuous and uniform film cannot be formed.
Preferably, in the monomer A solution, the concentration of the monomer A is 20-200 mmol/L; in the monomer B solution, the concentration of the monomer B is 0.1-100 mmol/L.
More preferably, the monomer B is succinyl chloride and/or suberoyl chloride; in the monomer B solution, the concentration of the monomer B is 0.1-20 mmol/L.
Further preferably, the monomer B is toluene diisocyanate and/or hexamethylene diisocyanate; in the monomer B solution, the concentration of the monomer B is 1-100 mmol/L.
Most preferably, the monomer A is tetra (4-aminophenyl) ethylene, and the concentration of the monomer A in the monomer A solution is 70-90 mmol/L; the monomer B is toluene diisocyanate, and the concentration of the monomer B in the monomer B solution is 1-20 mmol/L.
The base material is at least one of glass, silicon wafers, metal plates and polyvinylidene fluoride plates. The surface tension of different substrates is different, and the solid surface tension is increased to be beneficial to spreading of liquid on the solid surface. Preferably, the substrate is glass or silicon wafer.
In the step (2), the thickness of the liquid film is 50 μm-2 mm.
The thickness of the liquid film affects the uniformity and stability of the coating, and an increase in the thickness of the liquid film is advantageous for maintaining the coating stable during the reaction, but increases the amount of monomer used.
Preferably, the thickness of the liquid film is 100 to 500. mu.m.
In the step (3), the time of interfacial polymerization reaction is 1 s-12 h; the temperature of the interfacial polymerization reaction is 0-120 ℃.
Further preferably, the time of the interfacial polymerization reaction is 10 min-3 h; the temperature of the interfacial polymerization reaction is 20-50 ℃.
In the step (4), the detergent is at least one of water, ethanol and N-methyl pyrrolidone; the temperature is 5-95 ℃.
Preferably, the detergent is ethanol.
The drying can be selected from drying or natural airing in the air.
The invention also provides the aggregation-induced emission polymer film prepared by the macro preparation method.
Compared with the prior art, the invention has the beneficial effects that:
(1) according to the macro preparation method, the monomer A with the aggregation-induced emission effect is coated on the base material, and then is immersed in the non-co-soluble organic solvent for interfacial polymerization, so that macro preparation of the film with the aggregation-induced emission effect can be realized;
(2) the coating method can control the thickness of the liquid film, greatly reduces the monomer consumption and further reduces the production cost;
(3) the interfacial polymerization reaction is carried out on the surface of the liquid film, and the generated film has stable and uniform structure, so that the method has excellent high efficiency and stability;
(4) the preparation method has the advantages of mild reaction conditions, low equipment requirement and simple operation flow.
Drawings
FIG. 1 is a schematic flow chart of a macro-fabrication method of an aggregation-induced emission polymer thin film according to the present invention;
FIG. 2 is a fluorescence emission curve of the aggregation-induced emission thin film prepared in example 1.
Detailed Description
Example 1
The method for macro-preparing the aggregation-induced emission polymer thin film of the embodiment is performed according to the following steps, as shown in fig. 1:
(1) 0.06g of tetra (4-aminophenyl) ethylene monomer having aggregation-induced emission characteristics was weighed and added to 2mL of 1-butyl-3-methylimidazolium tetrafluoroborate, and the monomer was sufficiently dissolved by sonication for 30 minutes while setting the water bath temperature of the ultrasonic dissolver to 40 ℃ to obtain a uniform solution (solution A). Then, a smooth glass plate of 12cm × 12cm in size was prepared, 2mL of the solution was transferred onto the glass plate, and the monomer solution was uniformly coated on the glass plate with a 200 μm thick doctor bar;
(2) 1.45g of toluene diisocyanate was dissolved in 200mL of hexane to obtain a solution B. The glass plate coated with solution a was placed in an open reaction cell, after which solution B was carefully poured in and tetrakis (4-aminophenyl) ethylene and toluene diisocyanate reacted rapidly at the interface of 1-butyl-3-methylimidazolium tetrafluoroborate and hexane to form a polyurea film. It takes about 20 minutes for the reaction to proceed sufficiently, during which time the reaction cell is sealed to reduce hexane evaporation and keep solution B properties stable;
(3) and after the reaction is completed, taking the glass plate out of the reaction tank, putting the glass plate into ethanol, enabling the polyurea film on the glass plate to fall off under the action of surface tension, and standing for a period of time to fully clean impurities in the film. After the film is stable, the film is supported by a PET film, taken out and dried to obtain the fluorescent polyurea film, and then the fluorescent polyurea film is rolled and stored.
The implementation effect is as follows: an intact unbroken polymer film with aggregation-induced emission effect with a thickness of about 18 μm, which emits green fluorescence under uv illumination, with a maximum emission wavelength of 490nm, can be obtained, as shown in figure 2.
Examples 2 to 4
The solvent 1-butyl-3-methylimidazolium tetrafluoroborate used in example 1 was replaced by 1-ethyl-3-methylimidazolium tetrafluoroborate, 1-hexyl-3-methylimidazolium tetrafluoroborate, 1-butyl-3-methylimidazolium bistrifluoromethylsulphonylimide, respectively, and the remaining conditions were identical to those of example 1. The experimental results of examples 1 to 4 are shown in Table 1.
TABLE 1 Experimental results of preparing aggregation-induced emission thin films by different ionic liquid solvents
As can be seen from the data in Table 1, the selected ionic liquids can be uniformly spread on the glass plate, and good liquid film stability is maintained. The selection of the ionic liquid has a significant effect on the thickness of the film to be produced. The viscosity of the ionic liquid is gradually increased along with the increase of the carbon chain length in the cation of the ionic liquid, and the thickness of the film prepared under the same monomer concentration is reduced, which shows that in the reaction process, the high-viscosity solvent can limit the diffusion reaction rate of the monomer, so that the polymer growth rate is reduced, and the film is thinned.
Examples 5 to 7
The smooth glass plate used in example 1 was replaced with a smooth silicon wafer, a stainless steel plate, and polyvinylidene fluoride, respectively, and the remaining conditions were kept the same as in example 1. The experimental results of examples 5 to 7 are shown in Table 2.
TABLE 2 Experimental results of preparing aggregation-induced emission films on different substrates
As can be seen from Table 2, the selected substrate affects the spreading behavior of the ionic liquid solution, but does not significantly affect the structure of the prepared film. Different substrates have different wetting behaviors due to the difference of chemical properties and the difference of affinity between the ionic liquids.
Examples 8 to 10
The thickness of the coating scraped in example 1 was changed to 100. mu.m, 250. mu.m, and 500. mu.m, respectively, and the remaining conditions were kept the same as in example 1. The experimental results of examples 8 to 10 are shown in Table 3.
TABLE 3 Experimental results for preparing aggregation-induced emission thin films with different liquid film thicknesses
As can be seen from examples 8-10, the liquid film thickness affects its stability, and an excessively thin solution coating shrinks under the action of surface tension, so that a continuous and uniform film shape cannot be maintained, thereby affecting the final film-forming quality. However, when the thickness of the liquid film is more than 100 μm, the liquid film can be kept stable insufficiently, the amount of the monomer in the polymerization process is relatively sufficient, and the thickness has little influence on the film forming property and the thickness of the finally prepared film.
Example 11
The polyisocyanate monomer used in example 1 was changed to hexamethylene diisocyanate, the monomer concentration was 40mmol/L (6.73g/L), the reaction time was extended to 1 hour or more, and the remaining conditions were the same as in example 1. The experimental results of example 11 are shown in table 4.
The fluorescence emission of the film generated by the system is still strong under the excitation of ultraviolet light, which shows that the method can effectively prepare the aggregation-induced luminescence polyurea film.
Example 12
The conditions for the remainder were the same as in example 1 except that the monomer in the organic solvent phase used in example 1 was changed to trimesoyl chloride, the monomer concentration was 6mmol/L (1.59g/L), and the reaction time was 10 minutes. The experimental results of example 12 are shown in table 4.
The generated film has weak fluorescence intensity, which indicates that the introduction of trimesoyl chloride is not beneficial to the close packing of molecular chain segments, can reduce the fluorescence emission capability of the film,
example 13
The organic solvent phase used in example 1 was changed to succinyl chloride as a monomer, the monomer concentration was 6mmol/L (0.93g/L), the reaction time was 10 minutes, and the remaining conditions were the same as in example 1. The experimental results of example 13 are shown in table 4.
The system can rapidly prepare a large-area polyamide film, and the film shows good photoluminescence property.
Example 14
The aggregation inducing luminescent monomer used in example 1 was changed to 1, 2-diphenyl-1, 2-bis (4-aminophenyl) ethylene, the monomer concentration was 80mmol/L (29.7g/L), the reaction time was 20 minutes, and the remaining conditions were the same as in example 1. The experimental results of example 14 are shown in table 4.
The system produces films with increased thickness, but still maintains the uniform and stable film morphology, and emits intense fluorescence under ultraviolet excitation.
Example 15
The aggregation inducing luminescence monomer used in example 1 was changed to tetrakis- (4-hydroxyphenyl) ethylene, the monomer concentration was 100mmol/L (39.6g/L), the reaction time was 2 hours, the reaction temperature was 60 ℃, and the remaining conditions were the same as in example 1. The experimental results of example 15 are shown in table 4.
The system can prepare a cross-linked polyurethane film which emits stronger fluorescence under the excitation of ultraviolet light.
TABLE 4 Experimental results of preparing aggregation-induced emission thin films from different monomers
As can be seen from Table 4, the method has good universality for monomers with different structures, although different monomers need different reaction durations due to different reactivity of functional groups, the method can be used for preparing films with aggregation-induced emission effects, the fluorescence intensity of the films under ultraviolet illumination changes along with the difference of the structures of the monomers, and the difference of fluorescence properties may be caused by different movement restriction action intensities of different polymer structures on tetraphenyl ethylene groups.
The above-mentioned embodiments are intended to illustrate the technical solutions and advantages of the present invention, and it should be understood that the above-mentioned embodiments are only specific embodiments of the present invention, and are not intended to limit the present invention, and any modifications, additions, equivalents, etc. made within the scope of the principles of the present invention should be included in the scope of the present invention.
Claims (10)
1. A macro preparation method of an aggregation-induced emission polymer film is characterized by comprising the following steps:
(1) dissolving a monomer A in an ionic liquid to obtain a monomer A solution; dissolving the monomer B in an organic solvent to obtain a monomer B solution;
the monomer A is polyamine, polyalcohol and/or polyphenol with aggregation-induced emission characteristics;
the monomer B is polyacyl chloride and/or polyisocyanate;
(2) coating the monomer solution A on a substrate to form a liquid film with uniform thickness;
(3) placing the base material coated with the uniform liquid film prepared in the step (2) in a monomer solution B for interfacial polymerization reaction to generate an aggregation-induced emission polymer film on the surface of the base material;
(4) taking out the base material after the interfacial polymerization reaction, and immersing the base material into a detergent to automatically drop the generated aggregation-induced emission polymer film from the base material; and then drying and rolling the aggregation-induced emission polymer film.
2. The macro-scale process for preparing aggregation-induced emission polymer thin films according to claim 1, wherein the monomer A is at least one of 1, 2-diphenyl-1, 2-bis (4-aminophenyl) ethylene, tetrakis (4-aminophenyl) ethylene, 1, 2-diphenyl-1, 2-bis (4-hydroxyphenyl) ethylene, tetrakis (4-hydroxyphenyl) ethylene, 1, 2-diphenyl-1, 2-bis (4-carboxyphenyl) ethylene and tetrakis (4-carboxyphenyl) ethylene.
3. The process for the macro-preparation of an aggregation induced emission polymer thin film according to claim 1, wherein the ionic liquid is at least one of 1-ethyl-3-methylimidazolium tetrafluoroborate, 1-propyl-3-methylimidazolium tetrafluoroborate, 1-butyl-3-methylimidazolium tetrafluoroborate, 1-hexyl-3-methylimidazolium tetrafluoroborate, 1-octyl-3-methylimidazolium tetrafluoroborate, 1-ethyl-3-methylimidazolium bistrifluoromethylsulfonyl imide, 1-butyl-3-methylimidazolium bistrifluoromethylsulfonyl imide and bistrifluoromethylsulfonyl imide quaternary ammonium salts.
4. The method of claim 1, wherein said monomer B is at least one of trimesoyl chloride, succinyl chloride, adipoyl chloride, suberoyl chloride, toluene diisocyanate, diphenylmethane diisocyanate, hexamethylene diisocyanate, and naphthalene diisocyanate.
5. The method of claim 1, wherein the organic solvent is at least one of n-hexane, n-octane, n-dodecane, isoparaffin, toluene, dichloroethane, trichloroethane, and chloroform.
6. The macro preparation method of the aggregation-induced emission polymer thin film according to claim 1, wherein in the monomer A solution, the concentration of the monomer A is 20-200 mmol/L; in the monomer B solution, the concentration of the monomer B is 0.1-100 mmol/L.
7. The macro-preparation method of aggregation-induced emission polymer thin film according to claim 1, wherein in the step (2), the thickness of the liquid film is 50 μm to 2 mm.
8. The macro-preparation method of aggregation-induced emission polymer thin film according to claim 1, wherein in the step (3), the time of interfacial polymerization reaction is 1 s-12 h; the temperature of the interfacial polymerization reaction is 0-120 ℃.
9. The macro-production method of aggregation inducing luminescent polymer thin film according to claim 1, wherein in the step (4), the detergent is at least one of water, ethanol and N-methylpyrrolidone; the temperature is 5-95 ℃.
10. An aggregation-induced emission polymer thin film, characterized by being prepared by the macro-preparation method of claim 1.
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