CN113462380A - Organic gel for realizing triplet annihilation photon up-conversion in air state and preparation method and application thereof - Google Patents
Organic gel for realizing triplet annihilation photon up-conversion in air state and preparation method and application thereof Download PDFInfo
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Abstract
The invention provides an organic gel for realizing triplet annihilation photon up-conversion in an air state, a preparation method and application thereof.
Description
Technical Field
The invention relates to the technical field of organic photoelectric materials and high polymer materials, in particular to an organogel for realizing triplet annihilation photon up-conversion in an air state and a preparation method and application thereof.
Background
Triplet-Triplet annihilation based photon up-conversion (TTA-UC) is a technology for converting low-energy light into high-energy light, can function with low excitation intensity and an incoherent excitation source, and is the leading edge of the next generation of renewable energy device technology. Effective utilization of near-infrared light is attracting attention in energy and biological applications including bioimaging, photodynamic therapy, photocatalysis, drug delivery, etc., and the TTA-UC technology, which can convert low-energy light such as near-infrared light into high-energy light, is a focus of attention because the near-infrared light exhibits good tissue transparency but the photon energy in this region is too weak.
TTA-UC usually occurs in organic solvents, and to date, the most efficient TTA-UC systems are achieved in molecularly dispersed solutions, since they allow rapid diffusion of excited molecules, facilitating intermolecular collisions and energy transfer, however, excited triplet states are easily quenched by dissolved oxygen in organic solvents, and therefore must be operated under severe anoxic conditions, and organic solvents are volatile, which severely limits the application of TTA-UC. Chinese patent CN112048076A discloses a ternary supramolecular self-assembly up-conversion gel and a preparation method and application thereof, wherein a photosensitizer is used as a donor, a 9, 10-diphenylanthracene derivative containing amino is used as an acceptor, and the gel is self-assembled in an organic solvent through triple hydrogen bond action with a gel factor containing a multi-ureido group to prepare the gel which is used as the up-conversion gel, has certain mechanical strength, can not volatilize, and can realize up-conversion in an air state, but the gel is opaque and serious in scattering, needs to be solidified at a lower temperature, does not have certain shape and mechanical strength at room temperature, and the application of the gel at the room temperature is greatly limited.
Disclosure of Invention
The invention aims to solve the technical problems of the existing up-conversion gel carrier that the carrier is opaque, the scattering is serious, and the carrier can not be used at room temperature, and provides the organic gel which can realize the up-conversion of triplet annihilation photons in an air state, can be used as the up-conversion carrier, has high transparency, can not generate scattering, has certain shape and mechanical strength at room temperature, and can realize the up-conversion of triplet annihilation photons at room temperature and in the air state.
The invention further aims to provide a preparation method of the organic gel for realizing triplet annihilation photon up-conversion in an air state.
Another object of the present invention is to provide an application of the organic gel to realize the conversion of triplet annihilation photons in an air state.
The above purpose of the invention is realized by the following technical scheme:
the organic gel for realizing triplet annihilation photon upconversion in the air state is prepared by taking polyvinyl octyl aldehyde as a carrier, and carrying out self-assembly on the polyvinyl octyl aldehyde, a photosensitizer and an acceptor, wherein the acetalization rate of the polyvinyl octyl aldehyde is 11% -13%, and the molar ratio of the photosensitizer to the acceptor to the polyvinyl octyl aldehyde is 1: 46-460: 21000-110000.
The invention utilizes polyvinyl octyl aldehyde as a carrier of the up-conversion gel, forms the up-conversion organic gel with the photosensitizer and the receptor through self-assembly, and can form a spiral self-assembly structure through self-assembly because the polyvinyl octyl aldehyde has hydroxyl with large polarity and alkyl chain with small polarity, the affinity between the alkyl chain and the photosensitizer and the receptor is better, so that the alkyl chain with small polarity and a dye pair (the photosensitizer and the receptor) are positioned in the spiral structure, and the hydroxyl with large polarity and N, N-dimethylformamide are positioned outside the spiral structure, thereby avoiding triplet excitons from being quenched by oxygen in the air, and realizing the up-conversion of triplet annihilation photons in an air state; in addition, the polyvinyl octyl acetal with a certain acetal rate is used as a carrier of the up-conversion organogel, can be dissolved in a hot solvent at 90-100 ℃, can form the organogel after being cooled to room temperature, has high transparency, does not generate scattering, has certain shape and certain mechanical property at room temperature, can perform up-conversion at room temperature in an air state, has high up-conversion efficiency, and has the common performance advantages of a classical fluorescent polymer solution and a solid material.
Preferably, the molar ratio of the photosensitizer to the receptor to the polyvinyl octyl acetal is 1: 92-230: 82000-110000.
Preferably, the photosensitizer is one or more of octaethylporphyrin platinum, tetraphenylporphyrin platinum, and planar-tris (2-phenylpyridyl-N, C2') iridium (III).
More preferably, the photosensitizer is platinum octaethylporphyrin.
Preferably, the receptor is one or more of 9, 10-diphenyl anthracene, perylene and pyrene.
More preferably, the receptor is 9, 10-diphenylanthracene.
Preferably, the concentration of the platinum octaethylporphyrin is 22. mu. mmol/L.
Preferably, the concentration of the 9, 10-diphenylanthracene is 1-10 mmol/L.
Preferably, the concentration of the polyvinyl octyl acetal is 20-110 mg/mL.
The structural general formula of the polyvinyl octyl acetal is shown as the following formula (I):
wherein: (2 × x)/((2 × x + y)) -11% to 13%.
The preparation method for realizing the triplet annihilation photon up-conversion organogel in the air state comprises the following steps:
s1, uniformly mixing polyvinyl octyl aldehyde and N, N-dimethylformamide at the temperature of 105-115 ℃ for 2-3 hours to obtain a polyvinyl octyl aldehyde solution;
s2, uniformly mixing the polyvinyl octyl acetal solution prepared in the step S1 with a photosensitizer and a receptor at the temperature of 80-100 ℃ for 0.2-1.0 h to obtain a mixed solution, vacuumizing to remove bubbles, injecting the mixed solution into a mold in an air state while the mixed solution is hot, and cooling to form the up-conversion organogel.
Preferably, the concentration of the polyvinyl caprylaldehyde solution in the step S1 is 90-110 mg/mL.
Preferably, the temperature of step S1 is 110 ℃ and the time is 3.0 h.
Preferably, the reaction temperature of step S2 is 90 ℃ and the reaction time is 0.5 h.
Preferably, in the step S1, the preparation method of the polyvinyl acetal comprises the steps of dissolving polyvinyl alcohol in an organic solvent, and uniformly mixing at 90-100 ℃ for 1.0-2.0 hours to obtain a polyvinyl alcohol solution; and then mixing the polyvinyl alcohol solution with a strong acid catalyst for reaction, and then adding n-octanal for 1-4 hours at the reaction temperature of 60-65 ℃ to obtain the polyvinyl octanal.
Preferably, the temperature of the polyvinyl alcohol dissolved in the organic solvent is 60 ℃ and the time is 3.0 h.
Preferably, the strong acid catalyst is p-toluenesulfonic acid.
Preferably, the mass ratio of the polyvinyl alcohol to the p-toluenesulfonic acid to the n-octanal is 10: 0.8-1.0: 4 to 6.
More preferably, the mass ratio of the polyvinyl alcohol to the p-toluenesulfonic acid is 10: 0.86: 4.94.
preferably, the organic solvent is dimethyl sulfoxide.
Preferably, the molecular weight of the polyvinyl alcohol is 146000-186000.
The invention also protects the application of the organic gel for realizing the conversion of triplet annihilation photons in the air state in a photoluminescence device.
Compared with the prior art, the invention has the beneficial effects that:
the invention selects polyvinyl octyl aldehyde as a carrier, forms a spiral self-assembly structure with a photosensitizer and a receptor through self-assembly, realizes triplet annihilation photon up-conversion organic gel in an air state, has high transparency, does not generate scattering, has certain shape and mechanical strength at room temperature, can be used as an up-conversion carrier, realizes triplet annihilation photon up-conversion in the air state and at room temperature, has good repeatability and stability, and can be widely applied to photoluminescence devices.
Drawings
Fig. 1a and 1b are diagrams of the preparation method of the upconversion organogel of example 1 and its upconversion in the air state, and fig. 1c and 1d are SEM images of the gel sample doped and undoped dye pairs.
FIG. 2 is a graph of normalized absorption of the receptor molecule 9, 10-diphenylanthracene and the photosensitizer platinum octaethylporphyrin alone in the upconverting organogel prepared in example 1.
FIG. 3 is a graph of normalized emission of the acceptor molecule 9, 10-diphenylanthracene and the photosensitizer platinum octaethylporphyrin alone in the upconverting organogel prepared in example 1.
Fig. 4 is a graph of upconversion emission intensity as a function of incident light power density for the upconverting organogels prepared in example 1.
FIG. 5 is a graph of the excitation threshold in the air state of the upconverting organogel prepared in example 1.
FIG. 6 is a graph showing the change of upconversion emission intensity at 434nm under heating-cooling cycle conditions in air state of the upconversion organogel prepared in example 1, with excitation light wavelength of 532nm and excitation power of 100 mW/cm2。
FIG. 7 is a graph of upconversion emission intensity as a function of temperature in the air state for the upconverting organogel prepared in example 1.
FIG. 8 is a graph of the variation of the upconversion emission intensity with excitation light irradiation time in the air state of the upconversion organogel prepared in example 1, with excitation power of 500mW/cm2。
Figure 9 is the mechanical tensile curve of the upconverting organogel prepared in example 1.
Detailed Description
The present invention will be further described with reference to specific embodiments, but the present invention is not limited to the examples in any way. The starting reagents employed in the examples of the present invention are, unless otherwise specified, those that are conventionally purchased.
Example 1
An organogel for realizing triplet annihilation photon up-conversion in an air state is prepared by taking octaethylporphyrin platinum as a photosensitizer, 9, 10-diphenylanthracene as an acceptor and polyvinyl octanal as a carrier, wherein the acetal rate of the polyvinyl octanal is 12%, and the organogel for realizing triplet annihilation photon up-conversion in the air state is prepared by self-assembly, wherein the molar ratio of the photosensitizer to the acceptor to the polyvinyl octanal is 1:150: 100000.
The preparation method for realizing the triplet annihilation photon up-conversion organogel in the air state comprises the following steps:
s1, adding 2.0g of polyvinyl alcohol (PVA) into 20mL of dimethyl sulfoxide (DMSO), and stirring at 90 ℃ for 2 hours until the PVA is completely dissolved; reducing the temperature to 60 ℃, adding a proper amount of p-toluenesulfonic acid as a strong acid catalyst, adding a proper amount of n-octyl aldehyde, and modifying polyvinyl alcohol; after reacting for a certain time, injecting the reactant into a saturated sodium bicarbonate aqueous solution to terminate the reaction and obtain a white flocculent crude product polyvinyl octyl aldehyde; putting the white solid into deionized water for further cleaning, freezing and drying to obtain a white solid, and weighing; dissolving polyvinyl octanal in N, N-Dimethylformamide (DMF), and stirring at 110 deg.C for 3 hr until white solid is completely dissolved; cooling to 90 ℃;
s2, adding receptor molecules of 9, 10-Diphenylanthracene (DPA) and photosensitizer octaethylporphyrin platinum (PtOEP), wherein the concentrations of the octaethylporphyrin platinum, the 9, 10-diphenylanthracene and the polyvinyl octyl acetal are 22 mu mol/L, 3.3mmol/L and 100mg/mL respectively, stirring until the materials are completely dissolved, and vacuumizing to remove bubbles; and (3) injecting the liquid into a mould and a cuvette in an air state when the liquid is hot for further characterization, and solidifying the solution at room temperature for 1-2 minutes to form the up-conversion organogel.
Example 2
The organogel of this example, which realizes triplet annihilation photon up-conversion in air, is different from example 1 in that the molar ratio of the photosensitizer, the acceptor, and the polyvinyl octanal is replaced with 1:46: 21000.
Example 3
The organogel for realizing triplet annihilation photon up-conversion in air state of this example is the same as example 1 except that the molar ratio of photosensitizer, acceptor and polyvinyl octanal is replaced by 1:460: 110000.
Example 4
The organogel of this example, which realizes triplet annihilation photon up-conversion in the air state, is different from example 1 in that the acetal ratio of polyvinyl octanal is replaced with 11%.
Example 5
The organogel of this example, which realizes triplet annihilation photon up-conversion in the air state, is different from example 1 in that the acetal ratio of polyvinyl octanal is replaced with 13%.
Comparative example 1
In this comparative example, platinum octaethylporphyrin and 9, 10-diphenylanthracene were dissolved in N, N-dimethylformamide at a molar ratio of 1:150 to obtain a mixed solution free from an up-conversion phenomenon in an air state.
Comparative example 2
This comparative example is similar to example 1 except that the acetal ratio of polyvinyl octanal is replaced by 20%, and the solution is only formed by dissolving polyvinyl octanal in a solvent, and an up-conversion organogel having a certain shape and a certain mechanical property cannot be formed at room temperature.
Comparative example 3
This comparative example is the same as example 1 except that the acetal content of polyvinyl octanal was replaced with 5%, and the reaction mixture was poured into saturated aqueous sodium bicarbonate solution under the same reaction conditions, and no white floc was precipitated, and the product could not be further purified.
Structural characterization and performance detection
The up-conversion organogel prepared in example 1 was used as a test object to test photophysical properties and performances thereof, and the test results are shown in fig. 1 to 8.
Example 1 process for preparing an upconverting organogel as shown in fig. 1a, it can be seen that the upconverting organogel prepared in example 1 is in a transparent state (fig. 1a), the transparent gel is not scattered, the upconversion in an air state is shown in fig. 1b, and the gel has a significant upconversion in an air state. The SEM images of the gel samples of the doped dye pairs (platinum octaethylporphyrin and 9, 10-diphenylanthracene) prepared in example 1 are shown in fig. 1c, and the SEM image of the cross-section of the gel without the doped dye pair is shown in fig. 1d, which indicates that the folds of the gel without the doped dye pair do not have a spiral structure, while the folds of the gel with the doped dye pair have a spiral structure, indicating that the gels with the doped dye pair self-assemble, resulting in a spiral self-assembled structure. The upconversion organogels prepared in examples 2 to 5 are self-assembled and have a spiral self-assembled structure.
The results in FIG. 2 show that the photosensitizer platinum octaethylporphyrin exhibits a Soret absorption band at 380nm, a Q absorption band at 534nm, and DPA has a maximum absorption at 375 nm. According to the results of fig. 2, the upconversion organogel prepared in example 1 was tested for fluorescence emission intensity as a function of incident light power density at an excitation wavelength of 532nm, and the results are shown in fig. 4, which shows that the upconversion organogel exhibits the strongest absorption peak at 434 nm.
The results in FIG. 3 show that PtOEP emits a phosphorescent peak at about 645nm in atmospheric air and that upon excitation of DPA with light having a wavelength of 375nm, intense blue fluorescence is observed, with a wavelength of 430 nm. The excitation threshold of the upconverting organogel according to the log-log plot of the integration of the upconversion emission area of fig. 3 is 30mW/cm as shown in fig. 52。
The upconversion organogel prepared in example 1 shows the upconversion emission intensity change at 434nm under the heating-cooling cycle conditions as shown in fig. 6, the gel is cooled from 90 ℃ to 30 ℃, the upconversion emission intensity is continuously enhanced, and the gel can be subjected to upconversion at room temperature and in an air state; the upconversion organogels prepared in the embodiments 2 to 5 can be subjected to upconversion at room temperature in an air state; after the gel is heated and dissolved, the up-conversion phenomenon almost disappears; the up-conversion emission intensity difference is not large after multiple heating-cooling cycles; the internal structure of the gel is recombined in cold and hot cycles, and effective triplet-triplet energy transfer (TTET) and triplet-triplet annihilation (TTA) up-conversion are simultaneously recovered, which indicates that the process has good repeatability.
The emission spectrum of the upconversion organogel prepared in example 1, measured at an excitation wavelength of 532nm, changing with temperature is shown in fig. 7, and it can be seen from the graph that the upconversion emission intensity is high in the range of 30-50 ℃, which shows that the self-assembly structure of the upconversion organogel has a good shielding effect on air, can perform upconversion in an air state and at room temperature, and as the temperature increases, the organogel is dissolved into a liquid state, the self-assembly structure disappears, the upconversion emission intensity decreases, and a rule of an inverse "S" type curve is presented.
The spectrum of upconversion emission intensity of the upconversion organogel prepared in example 1 with excitation wavelength of 532nm according to incident illumination time is shown in FIG. 8, and 500mW/cm is used in air2After 30 minutes of irradiation with excitation power, only a slight decay of the upconversion emission intensity at 434nm occurs. The results show that the up-conversion emission in the gel has good stability under continuous laser irradiation.
FIG. 9 is a mechanical tensile curve of the upconverting organogel having a maximum tensile length of 400% of the original length and a maximum tensile strength of 0.35MPa, indicating that the gel has good mechanical properties.
It should be understood that the above-described embodiments of the present invention are merely examples for clearly illustrating the present invention, and are not intended to limit the embodiments of the present invention. Other variations and modifications will be apparent to persons skilled in the art in light of the above description. And are neither required nor exhaustive of all embodiments. Any modification, equivalent replacement, and improvement made within the spirit and principle of the present invention should be included in the protection scope of the claims of the present invention.
Claims (10)
1. The organic gel for realizing triplet annihilation photon upconversion in the air state is characterized in that polyvinyl octyl aldehyde is used as a carrier, and is self-assembled with a photosensitizer and a receptor to prepare the organic gel for realizing triplet annihilation photon upconversion in the air state, wherein the acetal rate of the polyvinyl octyl aldehyde is 11% -13%, and the molar ratio of the photosensitizer to the receptor to the polyvinyl octyl aldehyde is 1: 46-460: 21000-110000.
2. The organogel for realizing triplet annihilation photon up-conversion in the air state according to claim 1, wherein the molar ratio of the photosensitizer to the receptor to the polyvinyl octanal is 1:92 to 230:82000 to 110000.
3. The organogel according to claim 1 or 2, wherein the photosensitizer is one or more of octaethylporphyrin platinum, tetraphenylporphyrin platinum, and planar-tris (2-phenylpyridyl-N, C2') iridium (iii).
4. The organogel according to claim 1 or 2, wherein the acceptor is one or more of 9, 10-diphenylanthracene, perylene, and pyrene.
5. The method for preparing the organic gel capable of realizing triplet annihilation photon up-conversion in the air state according to any one of claims 1 to 4, comprising the following steps:
s1, uniformly mixing polyvinyl octyl aldehyde and N, N-dimethylformamide at the temperature of 105-115 ℃ for 2-3 hours to obtain a polyvinyl octyl aldehyde solution;
s2, uniformly mixing the polyvinyl octyl acetal solution prepared in the step S1 with a photosensitizer and a receptor at the temperature of 80-100 ℃ for 0.2-1.0 h to obtain a mixed solution, vacuumizing to remove bubbles, injecting the mixed solution into a mold in an air state while the mixed solution is hot, and cooling to form the up-conversion organogel.
6. The method according to claim 5, wherein the concentration of the polyvinyl caprylaldehyde solution in the step S1 is 90-110 mg/mL.
7. The method according to claim 5, wherein the preparation method of the polyvinyl octanols in step S1 comprises dissolving polyvinyl alcohol in an organic solvent, mixing uniformly at 90-100 deg.C for 1.0-2.0 h to obtain a polyvinyl alcohol solution; and then mixing the polyvinyl alcohol solution with p-toluenesulfonic acid for reaction, and then adding n-octanal for reaction at the temperature of 60-65 ℃ for 1-4 h to obtain the polyvinyl octanal.
8. The preparation method according to claim 7, wherein the mass ratio of the polyvinyl alcohol to the p-toluenesulfonic acid to the n-octanal is 10: 0.8-1.0: 4 to 6.
9. The method according to claim 7, wherein the polyvinyl alcohol has a molecular weight of 146000 to 186000.
10. Use of the organogel according to any of claims 1 to 4 for achieving triplet annihilation photon up-conversion in the air state in a photoluminescent device.
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| CN113967450B (en) * | 2021-11-16 | 2024-04-12 | 中国科学院理化技术研究所 | Bioactive hydrogel with photon up-conversion function and preparation method and application thereof |
| CN115011328A (en) * | 2022-04-20 | 2022-09-06 | 中国科学院理化技术研究所 | Luminescent material based on carbohydrate oxygen-insulating matrix, preparation and application |
| CN115011328B (en) * | 2022-04-20 | 2024-01-23 | 中国科学院理化技术研究所 | Luminescent material based on saccharide oxygen-blocking matrix, preparation and application |
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