CN115894495A - Preparation method of pure organic room temperature phosphorescent material based on uric acid and phenylboronic acid derivative composite crystal - Google Patents
Preparation method of pure organic room temperature phosphorescent material based on uric acid and phenylboronic acid derivative composite crystal Download PDFInfo
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- 239000013078 crystal Substances 0.000 title claims abstract description 72
- LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 title claims abstract description 69
- TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 title claims abstract description 69
- 229940116269 uric acid Drugs 0.000 title claims abstract description 69
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical class OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 title claims abstract description 43
- 239000000463 material Substances 0.000 title claims abstract description 31
- 239000002131 composite material Substances 0.000 title claims abstract description 24
- 238000002360 preparation method Methods 0.000 title claims abstract description 19
- 239000000725 suspension Substances 0.000 claims abstract description 20
- -1 polytetrafluoroethylene Polymers 0.000 claims abstract description 16
- 238000006243 chemical reaction Methods 0.000 claims abstract description 13
- 238000001816 cooling Methods 0.000 claims abstract description 12
- 238000010438 heat treatment Methods 0.000 claims abstract description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229920001343 polytetrafluoroethylene Polymers 0.000 claims abstract description 11
- 239000004810 polytetrafluoroethylene Substances 0.000 claims abstract description 11
- 238000000034 method Methods 0.000 claims abstract description 4
- 238000009210 therapy by ultrasound Methods 0.000 claims abstract description 4
- 238000001035 drying Methods 0.000 claims abstract 4
- 238000002156 mixing Methods 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 238000002441 X-ray diffraction Methods 0.000 description 16
- 238000007605 air drying Methods 0.000 description 8
- 238000000295 emission spectrum Methods 0.000 description 8
- 230000005284 excitation Effects 0.000 description 8
- 238000000695 excitation spectrum Methods 0.000 description 8
- 238000001296 phosphorescence spectrum Methods 0.000 description 8
- 238000000527 sonication Methods 0.000 description 7
- CEBAHYWORUOILU-UHFFFAOYSA-N (4-cyanophenyl)boronic acid Chemical compound OB(O)C1=CC=C(C#N)C=C1 CEBAHYWORUOILU-UHFFFAOYSA-N 0.000 description 5
- VOAAEKKFGLPLLU-UHFFFAOYSA-N (4-methoxyphenyl)boronic acid Chemical compound COC1=CC=C(B(O)O)C=C1 VOAAEKKFGLPLLU-UHFFFAOYSA-N 0.000 description 5
- LBUNNMJLXWQQBY-UHFFFAOYSA-N 4-fluorophenylboronic acid Chemical compound OB(O)C1=CC=C(F)C=C1 LBUNNMJLXWQQBY-UHFFFAOYSA-N 0.000 description 5
- PXXNBNUKDKCMSA-UHFFFAOYSA-N [4-(oxomethylidene)cyclohexa-1,5-dien-1-yl]boronic acid Chemical compound OB(O)C1=CCC(=C=O)C=C1 PXXNBNUKDKCMSA-UHFFFAOYSA-N 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 230000007704 transition Effects 0.000 description 5
- CAYQIZIAYYNFCS-UHFFFAOYSA-N (4-chlorophenyl)boronic acid Chemical compound OB(O)C1=CC=C(Cl)C=C1 CAYQIZIAYYNFCS-UHFFFAOYSA-N 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- VBXDEEVJTYBRJJ-UHFFFAOYSA-N diboronic acid Chemical compound OBOBO VBXDEEVJTYBRJJ-UHFFFAOYSA-N 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 238000001027 hydrothermal synthesis Methods 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- XLGLMVCAOMQNJT-UHFFFAOYSA-N boric acid;chlorobenzene Chemical compound OB(O)O.ClC1=CC=CC=C1 XLGLMVCAOMQNJT-UHFFFAOYSA-N 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 238000003763 carbonization Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000003745 diagnosis Methods 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005496 eutectics Effects 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000005622 photoelectricity Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229910021642 ultra pure water Inorganic materials 0.000 description 1
- 239000012498 ultrapure water Substances 0.000 description 1
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Abstract
The invention belongs to the technical field of organic room temperature phosphorescent materials, and discloses a preparation method of a pure organic room temperature phosphorescent material based on a uric acid and phenylboronic acid derivative composite crystal. The preparation method comprises the following steps: step 1, dispersing uric acid and phenylboronic acid derivatives in water according to a certain proportion, and performing ultrasonic treatment for a period of time to obtain a suspension; and 2, transferring the suspension obtained in the step 1 into a polytetrafluoroethylene reaction kettle, heating for a period of time at a certain temperature, cooling to room temperature to obtain a pure organic room-temperature phosphorescent crystal, and drying the obtained crystal in a vacuum oven. The method has simple synthesis steps and mild conditions, and the prepared pure organic room temperature phosphorescent crystal can emit bright macroscopic phosphorescent emission at room temperature.
Description
Technical Field
The invention belongs to the technical field of organic room temperature phosphorescent materials, and relates to a preparation method of a pure organic room temperature phosphorescent material based on a uric acid and phenylboronic acid derivative composite crystal.
Background
The room temperature phosphorescent material has wide application in the fields of information encryption, sensing, photoelectricity, biological diagnosis and treatment and the like due to large Stokes displacement, high signal-to-noise ratio and long service life. Different from inorganic room temperature phosphorescent materials, pure organic room temperature phosphorescent materials have the advantages of low toxicity, low cost, easy processing and the like, and attract the wide attention of researchers. However, the pure organic room temperature phosphorescent material has a weak spin orbit coupling constant, and the triplet state is easily affected by temperature and oxygen, so that the ultra-long-life pure organic room temperature phosphorescent material is difficult to realize. However, room temperature phosphorescent materials are mainly inorganic materials (chem. Mater.2022,34,22,10068-10076) and metal organic complexes (Angew. Chem. Int. Ed.2018,57, 6279-6283) at present, but the application of the room temperature phosphorescent materials is greatly limited due to the problems of complex synthetic steps, difficult processing, heavy metal atom containing and the like. Therefore, it is important to develop a simple and efficient pure organic room temperature phosphorescent material, wherein the realization of organic room temperature phosphorescence through structural design and molecular stacking mode is a feasible method. For example, the intermolecular cross-over can be promoted by introducing a heteroatom into a molecule, and the non-radiative transition can be inhibited to realize the pure organic room temperature phosphorescence by forming a composite crystal through a two-component eutectic, which provides reference for developing a pure organic room temperature phosphorescence material.
Disclosure of Invention
The invention aims to provide a preparation method of a pure organic room-temperature phosphorescent material based on a uric acid and phenylboronic acid derivative composite crystal aiming at the problems of short room-temperature phosphorescence service life and low quantum efficiency of the existing synthesis.
In order to achieve the purpose, the invention adopts the technical scheme that:
a preparation method of a pure organic room temperature phosphorescent material based on a uric acid and phenylboronic acid derivative composite crystal comprises the following steps:
mixing uric acid and phenylboronic acid derivatives in a mass ratio of 1:1 to 16 are dispersed in ultrapure water, and the ultrasonic time is 30min. Then transferring the solution into a polytetrafluoroethylene reaction kettle, and heating the solution at the temperature of between 60 and 150 ℃ for 3 to 9 hours. After cooling, the obtained crystal is heated in a vacuum oven at the temperature of 50 ℃ for 48h.
Wherein the structural formula of uric acid is as follows:
the structural formula of the phenylboronic acid derivative is any one of the following 1-8:
according to the preparation method, the uric acid and the phenylboronic acid derivative form a composite crystal to form a hydrogen bond effect, so that non-radiative transition is inhibited, and heteroatom enhanced intersystem crossing is realized, thereby realizing the pure organic room-temperature phosphorescent material with long service life and high quantum efficiency.
The uric acid in the invention has a plurality of amido bonds, can provide n → pi transition, enhance spin-orbit coupling and promote intersystem crossing. Meanwhile, amide bond energy of uric acid and aryl boron hydroxyl form a hydrogen bond to inhibit non-radiative transition, so that long-life and high-efficiency pure organic room-temperature phosphorescence is realized. However, uric acid and phenylboronic acid derivatives have low solubility in water and are difficult to form strong hydrogen bonding with each other. Considering that the solubility of the uric acid and the phenylboronic acid derivative can be increased by increasing the temperature and the pressure, and the collision probability of the uric acid and the phenylboronic acid derivative is enhanced, so that a stronger hydrogen bond is formed, and therefore, the preparation of the room-temperature phosphorescent material can be realized by a hydrothermal method. When the material is cooled to room temperature, the solubility of the uric acid and the phenylboronic acid derivative is reduced, crystals are separated out, and the rigid environment provided by the crystals further inhibits non-radiative transition, so that the material can emit long-life and high-efficiency room-temperature phosphorescence under the irradiation of an ultraviolet lamp. Of course, the temperature is not too high, and the uric acid and the phenylboronic acid derivative are easily dehydrated and carbonized due to the too high temperature.
The invention has the beneficial effects that: according to the invention, the solubility of uric acid and phenylboronic acid derivatives and the collision probability of uric acid and phenylboronic acid derivative molecules are increased by a hydrothermal method, crystals are precipitated after cooling, and strong hydrogen bonds between molecules and in molecules are formed.
Drawings
FIG. 1 shows phosphorescence emission and excitation spectra of a uric acid and phenylboronic acid composite crystal.
FIG. 2 is an X-ray diffraction spectrum of a complex crystal of uric acid and phenylboronic acid.
FIG. 3 is the phosphorescence emission and excitation spectrum of uric acid and p-phenylboronic acid composite crystal.
FIG. 4 is the X-ray diffraction spectrum of the uric acid and terephthalic diboronic acid composite crystal.
FIG. 5 shows phosphorescence emission and excitation spectra of a complex crystal of uric acid and 4-cyanophenylboronic acid.
FIG. 6 is an X-ray diffraction pattern of a complex crystal of uric acid and 4-cyanophenylboronic acid.
FIG. 7 shows phosphorescence emission and excitation spectra of uric acid and 4-fluorobenzeneboronic acid composite crystals.
FIG. 8 is an X-ray diffraction spectrum of a composite crystal of uric acid and 4-fluorobenzeneboronic acid.
FIG. 9 shows phosphorescence emission and excitation spectra of a complex crystal of uric acid and 4-chlorobenzeneboronic acid.
FIG. 10 is the X-ray diffraction spectrum of the composite crystal of uric acid and 4-chlorobenzene boric acid.
FIG. 11 shows phosphorescence emission and excitation spectra of a complex crystal of uric acid and 4-methoxyphenylboronic acid.
FIG. 12 is the X-ray diffraction pattern of the compound crystal of uric acid and 4-methoxyphenylboronic acid.
FIG. 13 shows phosphorescence emission and excitation spectra of a complex crystal of uric acid and 4-carbonylphenylboronic acid.
FIG. 14 is an X-ray diffraction pattern of a complex crystal of uric acid and 4-carbonylphenylboronic acid.
FIG. 15 shows phosphorescence emission and excitation spectra of a uric acid and 4-carbonylmethoxyphenylboronic acid composite crystal.
FIG. 16 is the X-ray diffraction pattern of the compound crystal of uric acid and 4-carbonyl methoxy phenylboronic acid.
Detailed Description
The following further describes the specific embodiments of the present invention with reference to the technical solutions and the accompanying drawings.
Example 1
The embodiment discloses a preparation method of a pure organic room temperature phosphorescent material based on a uric acid and phenylboronic acid composite crystal, which comprises the following steps:
mixing uric acid and phenylboronic acid in a mass ratio of 1: 0-16 reactants are respectively dispersed in 10ml of water and then are subjected to ultrasonic treatment for 30min to obtain a suspension. And then, quickly transferring the suspension into a polytetrafluoroethylene reaction kettle, and heating the reaction kettle in a forced air drying oven at the temperature of between 60 and 150 ℃ for 3 to 9 hours. After cooling to room temperature, crystals were obtained, which were then dried in a vacuum oven at 50 ℃ for 48h.
Uric acid and phenylboronic acid have the following structures:
table 1 reports the room temperature phosphorescence of uric acid and phenylboronic acid at different mass ratios:
preferably, the mass ratio of the uric acid to the phenylboronic acid is 1 in the following experiments: 1 was tested. The preparation of room temperature phosphorescence is difficult to realize when the reactant ratio is too high or too low.
Table 2 reports the room temperature phosphorescence of uric acid and phenylboronic acid at different temperatures:
preferably, we will take uric acid and phenylboronic acid to react at 120 ℃ in the following experiments. Too low a temperature is not conducive to the dissolution of the reactants, and too high a temperature may cause carbonization of the raw materials.
Table 3 reports the room temperature phosphorescence of uric acid and phenylboronic acid at different reaction times:
preferably, we will take uric acid and phenylboronic acid to react for 3h in all the following experiments. The reaction time is prolonged and the reaction result of 3h is not greatly different, and the reaction time of 3h is selected in order to save time and resources.
As shown in the phosphorescence spectrum of FIG. 1, the optimal phosphorescence emission wavelength of the synthesized crystal is 484nm, and the optimal excitation wavelength is 277nm. Indicating that the crystal emits cyan phosphorescence. The structure of the crystal can be seen from the X-ray diffraction pattern of FIG. 2.
Example 2
The embodiment discloses a preparation method of a pure organic room temperature phosphorescent material based on uric acid and p-phenylboronic acid composite crystals, which comprises the following steps:
800mg of uric acid and 800mg of p-phenylboronic acid were dispersed in 10ml of water, followed by sonication for 30min to obtain a suspension. And then, quickly transferring the suspension into a polytetrafluoroethylene reaction kettle, and heating for 3 hours in a 120-DEG C forced air drying oven. After cooling to room temperature, crystals were obtained, which were then dried in a vacuum oven at 50 ℃ for 48h.
The structure of uric acid and terephthalic diboronic acid is as follows:
as shown in the phosphorescence spectrum of FIG. 3, the optimal phosphorescence emission wavelength of the synthesized crystal is 505nm, and the optimal excitation wavelength is 258nm. Indicating that the crystal emits green phosphorescence. The structure of the crystal can be seen from the X-ray diffraction pattern of FIG. 4.
Example 3
The embodiment discloses a preparation method of a pure organic room temperature phosphorescent material based on a uric acid and 4-cyanophenylboronic acid composite crystal, which comprises the following steps:
800mg of uric acid and 800mg of 4-cyanophenylboronic acid were dispersed in 10ml of water, followed by sonication for 30min to obtain a suspension. And then, quickly transferring the suspension into a polytetrafluoroethylene reaction kettle, and heating for 3 hours in a 120 ℃ forced air drying oven. After cooling to room temperature, crystals were obtained, which were then dried in a vacuum oven at 50 ℃ for 48h.
Uric acid and 4-cyanophenylboronic acid have the following structures:
as shown in the phosphorescence spectrum of FIG. 5, the optimal phosphorescence emission wavelength of the synthesized crystal is 485nm, and a shoulder peak is positioned at 517nm; the optimum excitation wavelength is 258nm, and a shoulder 295nm is also provided. Indicating that the crystal emits green phosphorescence. The structure of the crystal can be seen from the X-ray diffraction pattern of FIG. 6.
Example 4
The embodiment discloses a preparation method of a pure organic room temperature phosphorescent material based on a uric acid and 4-fluorobenzeneboronic acid composite crystal, which comprises the following steps:
800mg of uric acid and 800mg of 4-fluorophenylboronic acid were dispersed in 10ml of water, followed by sonication for 30min to obtain a suspension. And then, quickly transferring the suspension into a polytetrafluoroethylene reaction kettle, and heating for 3 hours in a 120 ℃ forced air drying oven. After cooling to room temperature, crystals were obtained, which were then dried in a vacuum oven at 50 ℃ for 48h.
Uric acid and 4-fluorophenylboronic acid have the following structures:
as shown in the phosphorescence spectrum of FIG. 7, the optimal phosphorescence emission wavelength of the synthesized crystal is 500nm, and the optimal excitation wavelength is 267nm. Indicating that the crystal emits green phosphorescence. The structure of the crystal can be seen from the X-ray diffraction pattern of FIG. 8.
Example 5
The embodiment discloses a preparation method of a pure organic room temperature phosphorescent material based on a uric acid and 4-chlorobenzeneboronic acid composite crystal, which comprises the following steps:
800mg of uric acid and 800mg of 4-chlorobenzeneboronic acid were dispersed in 10ml of water, followed by sonication for 30min to obtain a suspension. And then, quickly transferring the suspension into a polytetrafluoroethylene reaction kettle, and heating for 3 hours in a 120 ℃ forced air drying oven. After cooling to room temperature, crystals were obtained, which were then dried in a vacuum oven at 50 ℃ for 48h.
Uric acid and 4-chlorobenzeneboronic acid have the following structures:
as shown in FIG. 9, the phosphorescence spectrum shows that the optimal phosphorescence emission wavelength of the synthesized crystal is 519nm, the optimal excitation wavelength is 316nm, and a shoulder peak is 277nm. Indicating that the crystal emits green phosphorescence. The structure of the crystal can be seen from the X-ray diffraction pattern of FIG. 10.
Example 6
The embodiment discloses a preparation method of a pure organic room temperature phosphorescent material based on a uric acid and 4-methoxyphenylboronic acid composite crystal, which comprises the following steps:
800mg of uric acid and 800mg of 4-methoxyphenylboronic acid were dispersed in 10ml of water, followed by sonication for 30min to obtain a suspension. And then, quickly transferring the suspension into a polytetrafluoroethylene reaction kettle, and heating for 3 hours in a 120 ℃ forced air drying oven. After cooling to room temperature, crystals were obtained, which were then dried in a vacuum oven at 50 ℃ for 48h.
Uric acid and 4-methoxyphenylboronic acid have the following structures:
as shown in the phosphorescence spectrum of FIG. 11, the synthesized crystal has an optimal phosphorescence emission wavelength of 492nm and an optimal excitation wavelength of 286nm. Indicating that the crystal emits green phosphorescence. The structure of the crystal can be seen from the X-ray diffraction pattern of FIG. 12.
Example 7
The embodiment discloses a preparation method of a pure organic room temperature phosphorescent material based on a uric acid and 4-carbonyl phenylboronic acid composite crystal, which comprises the following steps:
800mg of uric acid and 800mg of 4-carbonylphenylboronic acid were dispersed in 10ml of water, followed by sonication for 30min to obtain a suspension. And then, quickly transferring the suspension into a polytetrafluoroethylene reaction kettle, and heating for 3 hours in a 120 ℃ forced air drying oven. After cooling to room temperature, crystals were obtained, which were then dried in a vacuum oven at 50 ℃ for 48h.
Uric acid and 4-carbonylphenylboronic acid have the following structures:
as shown in the phosphorescence spectrum of FIG. 13, the synthesized crystal has an optimal phosphorescence emission wavelength of 574nm, an optimal excitation wavelength of 337nm, and a shoulder peak at 279nm. Indicating that the crystal emits orange-red phosphorescence. The structure of the crystal can be seen from the X-ray diffraction pattern of FIG. 14.
Example 8
The embodiment discloses a preparation method of a pure organic room temperature phosphorescent material based on a uric acid and 4-carbonyl methoxyphenylboronic acid composite crystal, which comprises the following steps:
800mg of uric acid and 800mg of 4-carbonylmethoxyphenylboronic acid were dispersed in 10ml of water, followed by sonication for 30min to obtain a suspension. And then, quickly transferring the suspension into a polytetrafluoroethylene reaction kettle, and heating for 3 hours in a 120 ℃ forced air drying oven. After cooling to room temperature, crystals were obtained, which were then dried in a vacuum oven at 50 ℃ for 48h.
Uric acid and 4-carbonyl methoxyphenylboronic acid have the following structures:
as shown in the phosphorescence spectrum of FIG. 15, the synthesized crystal has the optimum phosphorescence emission wavelength of 517nm, the optimum excitation wavelength of 273nm, and a shoulder at 310nm. Indicating that the crystal emits green phosphorescence. The structure of the crystal can be seen from the X-ray diffraction pattern of FIG. 16.
Finally, it should be noted that: the above embodiments are only used to illustrate the technical solution of the present invention, and not to limit the same; while the invention has been described in detail and with reference to the foregoing embodiments, it will be understood by those skilled in the art that: the technical solutions described in the foregoing embodiments may still be modified, or some or all of the technical features may be equivalently replaced; and the modifications or the substitutions do not make the essence of the corresponding technical solutions depart from the scope of the technical solutions of the embodiments of the present invention.
Claims (3)
1. A preparation method of a pure organic room temperature phosphorescent material based on a uric acid and phenylboronic acid derivative composite crystal is characterized by comprising the following steps:
step 1, mixing uric acid and phenylboronic acid derivatives according to a mass ratio of 1: 1-16, dispersing in water, and performing ultrasonic treatment to obtain a suspension;
wherein the structural formula of uric acid is as follows:
the structural formula of the phenylboronic acid derivative is as follows:
and 2, transferring the suspension obtained in the step 1 into a polytetrafluoroethylene reaction kettle, heating for 3-9 hours at the heating temperature of 120-150 ℃, cooling, and drying in a vacuum oven to obtain the pure organic room-temperature phosphorescent material.
2. The method according to claim 1, wherein the ratio of uric acid to phenylboronic acid derivative is 1: 1-16, dispersing in water, and carrying out ultrasonic treatment for 30min.
3. The method according to claim 1 or 2, wherein the drying temperature in step 2 is 50 ℃ and the drying time is 48h.
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Citations (4)
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|---|---|---|---|---|
| CN110272379A (en) * | 2019-07-12 | 2019-09-24 | 福州大学 | A kind of synthesis and its Application in Anti-counterfeiting of halogen atom-containing room temperature phosphorimetry material |
| CN112342017A (en) * | 2020-11-06 | 2021-02-09 | 山东大学 | Ultra-long-life room temperature phosphorescent material and preparation method and application thereof |
| CN112939881A (en) * | 2021-02-19 | 2021-06-11 | 南京邮电大学 | Bi-component organic room temperature phosphorescent material and preparation method thereof |
| WO2021173523A1 (en) * | 2020-02-24 | 2021-09-02 | Newave Pharmaceutical Inc. | Hot melt extruded solid dispersions containing a bcl2 inhibitor |
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110272379A (en) * | 2019-07-12 | 2019-09-24 | 福州大学 | A kind of synthesis and its Application in Anti-counterfeiting of halogen atom-containing room temperature phosphorimetry material |
| WO2021173523A1 (en) * | 2020-02-24 | 2021-09-02 | Newave Pharmaceutical Inc. | Hot melt extruded solid dispersions containing a bcl2 inhibitor |
| CN112342017A (en) * | 2020-11-06 | 2021-02-09 | 山东大学 | Ultra-long-life room temperature phosphorescent material and preparation method and application thereof |
| CN112939881A (en) * | 2021-02-19 | 2021-06-11 | 南京邮电大学 | Bi-component organic room temperature phosphorescent material and preparation method thereof |
Non-Patent Citations (1)
| Title |
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| ZHONG-XIA WANG，等: "Multiplexed ratiometric photoluminescent detection of pyrophosphate using anisotropic boron-doped nitrogen-rich carbon rugby ball-like nanodots", J. MATER. CHEM. B, vol. 6, 22 February 2018 (2018-02-22) * |
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