CN112011331A - Novel antimonate bromide luminescent material, luminescent film and preparation method thereof - Google Patents
Novel antimonate bromide luminescent material, luminescent film and preparation method thereof Download PDFInfo
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Abstract
The invention belongs to the technical field of functional materials, and particularly relates to a novel bromide antimonate luminescent material, namely a pentabromoantimonate benzyl substituted pyridinium, which is a compound consisting of pentabromoantimonate anions and benzyl substituted pyridine cations, and the preparation method comprises the following steps: (1) placing a certain amount of benzyl bromide and substituted pyridinium in a container, adding a solvent for dissolving, heating for reaction, and then concentrating and drying to obtain an oily substance; (2) a certain amount of Sb2O3Dissolving in hydrobromic acid, adding a certain amount of oily matter obtained in the step 1, heating for reaction, filtering, concentrating the obtained filtrate to obtain crystals, and further preparing the luminescent film by adopting an electrostatic spinning process. The novel antimonate bromide luminescent material and the luminescent film show good orange-red fluorescence effect under 365nm ultraviolet irradiation, and are optical materials with excellent performance. The preparation method has the advantages of simple operation, high yield, cost saving, wide application range and contribution to industrial popularization.
Description
Technical Field
The invention belongs to the technical field of functional materials, and particularly relates to a novel bromide antimonate luminescent material, namely pentabromoantimonate benzyl substituted pyridinium, a preparation method thereof and a luminescent film prepared from the same.
Background
Luminescent materials are one of the important components of modern social life, and are widely applied in the fields of energy, information, environment, medical care technology and the like. Over time, various types of light emitting materials have been developed, including organic and polymer emitters, transition metal complexes, rare earth doped phosphors, nanocrystals, and organic-inorganic hybrid perovskites. Phosphorescent metal complexes have enjoyed great success as one of the most important light-emitting materials in organic light-emitting diodes having internal quantum efficiencies close to 100%. However, most highly efficient phosphorescent complexes are based on iridium or platinum, they are neither earth-rich nor cost-effective, and their preparation often involves synthesis in multiple steps, which limits their potential applications in practical devices.
In recent years, organic-inorganic hybrid photoluminescent materials have become a hot spot for research in the field of photoluminescent materials. Most hybrid photoluminescent materials are metal-containing compounds, where the photoluminescence can be easily tuned by changing the metal center. At present, metals are mainly f-group elements, and the cost is high generally, so that the search of other low-cost and high-efficiency central metals for synthesizing the photoluminescent material is an urgent technical problem to be solved.
Disclosure of Invention
The invention aims to provide a novel brominated antimonate luminescent material which emits strong orange-red light under 365nm ultraviolet irradiation.
In order to achieve the purpose, the invention is realized by the following technical scheme:
the novel luminous material of the brominated antimonate is a compound consisting of pentabrominated antimony anions and benzyl substituted pyridine cations, and the chemical structure of the luminous material is shown as the following formula:
Further preferably, R is H or NH2(ii) a Namely, the novel luminescent material of the antimonic bromide is preferably benzyl pyridinium pentabromoantimonate [ BzPy]2[SbBr5](I) or pentabromoantimonic acid benzyl 4-aminopyridine salt [ Bz-4-NH2Py]2[SbBr5]（Ⅱ）。
Further preferably, the novel luminous material of the antimonic bromide is a crystal material, the crystal system is Monoclinic, and the space group isP21And/n. When R is H, the crystal material has unit cell parameters ofa=10.025-10.028 Å、b=24.191-24.197 Å、c=11.885-11.889 Å，β=105.361-105.369 °; when R is NH2When the crystal material has a unit cell parameter ofa=9.321-9.322 Å、b=12.621-12.622 Å、c=24.958-24.961 Å，β=99.665-99.667°。
The invention also provides a preparation method of the novel antimonous bromide luminescent material, which has the advantages of high yield, cost saving, easy operation and contribution to industrial production. The preparation method comprises the following steps:
(1) placing a certain amount of benzyl bromide and substituted pyridinium in a container, adding a solvent (preferably methanol) to dissolve, reacting at 65-70 ℃ (stirring and refluxing for 16-24 hours), concentrating (rotary evaporator), and drying to obtain an oily substance;
(2) a certain amount of Sb2O3Dissolved in hydrobromic acid and addedAdding a certain amount of the oily substance obtained in the step 1, heating for reaction (stirring and heating at 60-120 ℃ for 0.5-2 hours), then filtering, and concentrating the obtained filtrate (evaporating at room temperature) to obtain crystals.
Further preferably, when R is H, the reaction conditions in step (2) are that the mixture is heated at 100-120 ℃ for 0.5-2 hours with stirring; when R is NH2In the step (2), a proper amount of methanol is added before the reaction, and the reaction condition is that the mixture is stirred and heated for 0.5 to 2 hours at the temperature of between 60 and 70 ℃.
Preferably, the molar ratio of benzyl bromide to substituted pyridinium salt used is 1: (0.5-1.5), more preferably 1: 1.
preferably, Sb is used2O3And the mass ratio of the oil is 1: (1.7-1.9).
The invention also provides a novel luminous film of antimonous bromide, which is prepared by the following method: dissolving a certain amount of polyethylene oxide (PEO) in acetonitrile, and adding the obtained novel brominated antimonate luminescent material for dissolving to form a homogeneous spinning solution; and spinning the obtained spinning solution by adopting an electrostatic spinning process to obtain the luminescent film.
Preferably, the parameters of the electrostatic spinning process are as follows: the speed is 2.0 mL/h; the needle pitch collector is 9 cm; the voltage is 18 kV; the speed of the collecting drum was 236 revolutions per minute; the spinning time is 8 hours; ambient temperature is 25 ℃; the relative humidity is 40-70%.
Preferably, the mass ratio of the polyethylene oxide to the novel brominated antimonate luminescent material is (2-3): 1, and more preferably 8: 3.
The invention has the following positive and beneficial effects:
the novel antimonate bromide luminescent material and the luminescent film show good orange-red fluorescence effect under 365nm ultraviolet irradiation, and are optical materials with excellent performance. The preparation method is simple and convenient to operate and high in yield; the required instruments and equipment are simple and easy to operate; the consumption of the needed solvent is low, the cost is saved, the application range is wide, and the method is beneficial to industrial popularization.
Drawings
FIG. 1 is a crystal structure diagram (hydrogen atom omitted) of a novel antimonate bromide light-emitting material according to example 1 of the present invention;
FIG. 2 is a unit cell stacking diagram (hydrogen atom omitted) of the novel antimonate bromide luminescent material of example 1 according to the present invention;
FIG. 3 is a crystal structure diagram (hydrogen atom omitted) of a novel antimonate bromide light-emitting material according to example 2 of the present invention;
FIG. 4 is a unit cell stacking diagram (hydrogen atom omitted) of the novel antimonate bromide luminescent material of example 2 according to the present invention;
FIG. 5 is a solid UV-VIS absorption spectrum of the novel antimonate bromide phosphors of examples 1 and 2 of the present invention;
FIG. 6 is a fluorescence emission spectrum of the novel antimonate bromide light-emitting material according to example 1 of the present invention;
FIG. 7 is a fluorescence emission spectrum of a novel antimonate bromide light-emitting material according to example 2 of the present invention;
FIG. 8 is a graph showing the luminous effect of the novel antimonate bromide luminescent materials of examples 1 and 2 of the present invention (example 1 on the left, example 2 on the right);
FIG. 9 is a graph showing the luminous effect of the novel antimonate bromide luminescent films of examples 3 and 4 of the present invention (example 3 on the left and example 4 on the right).
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention is further described in detail with reference to the following embodiments. It should be understood that the specific embodiments described herein are merely illustrative of the invention and are not intended to limit the invention. The starting materials used in the following examples are commercially available unless otherwise specified, and the detection methods used therein are conventional unless otherwise specified. The following abbreviation [ SbBr5]2-Is a pentabromoantimony anion, [ BzPy]+Is benzyl pyridine cation, [ Bz-4-NH ]2Py]+Is a benzyl 4-aminopyridine cation.
Example 1:
a novel pentabromo antimonate benzyl pyridinium luminescent material is prepared by the following steps:
(1) adding 0.02 mol of benzyl bromide and 0.02 mol of pyridine into a 100mL conical flask, adding 35mL of methanol for dissolving, heating at 70 ℃, stirring and refluxing for 20h, and rotationally evaporating the solution at 45 ℃ to obtain viscous yellow liquid, namely brominated benzyl pyridinium [ BzPy ] Br.
(2) 1mmol of Sb2O3In a beaker, 10mL hydrobromic acid was added and dissolved, and then 2mmol [ BzPy ] was added]Br is heated and stirred for 1h at the temperature of 110 ℃ to obtain clear solution, and the clear solution is naturally volatilized for two weeks at normal temperature to generate yellow crystals, namely the pentabromoantimonic acid benzyl pyridinium [ BzPy [ ]]2[SbBr5](ii) a The yield was 77.8%.
Subjecting the obtained material to infrared spectrum detection, IR (cm)-1)：ν(C-H): 3117、3048，ν(C=C)：1626、1577、1484，ν(CH2)：1453，ν(C–N)：1287、1206、1157。
The obtained material is subjected to solid ultraviolet absorption spectrum detection, the spectrum is shown in figure 5, the absorption cut-off wavelengths are 480nm respectively, the corresponding optical band gaps are 2.40eV, the material has certain absorption capacity on visible light, the band gaps belong to the range of typical semiconductor materials, and the material is a potential optical material when being equivalent to the values of other brominated metal compounds researched as potential solar energy absorbents.
The resulting material was subjected to X-ray single crystal diffraction, and the crystallographic data are shown in Table 1, the crystal structure is shown in FIG. 1, and the unit cell packing is shown in FIG. 2. Fluorescence analysis is carried out on the obtained material, a photoluminescence spectrum is shown in figure 6, under the excitation wavelength of 400nm, the brominated antimonate shows a broadband orange-red emission peak between 580 and 750nm, and the maximum absorption peak is 684 nm.
The obtained material can emit obvious orange red light when the luminescent property detection is carried out under the irradiation of 365nm ultraviolet light, as shown in figure 8.
Example 2:
a novel pentabromo-antimonic acid benzyl-4-aminopyridine salt luminescent material is prepared by the following steps:
(1) taking 0.02 mol of benzyl bromide and 0.02 mol of 4-aminopyridine into a 100mL conical flask, adding 30mL of methanol, heating, stirring and refluxing at 60 ℃ for 20h, and rotationally evaporating the solution at 45 ℃ to evaporate the solventTo obtain viscous yellow liquid, namely the brominated benzyl 4-aminopyridine salt [ Bz-4-NH ]2Py]Br。
(2) 1mmol of Sb2O3Adding 1mL of hydrobromic acid into a beaker for dissolution, placing the beaker in a 100mL conical flask, and adding 2mmol of [ Bz-4-NH2Py]Adding 30mL of methanol into Br, heating and stirring at 60 ℃ for refluxing for 1h, filtering, recovering powder, putting the obtained filtrate into a small beaker, naturally volatilizing for two weeks at normal temperature to generate yellow crystals, and obtaining the pentabromoantimonic acid benzyl 4-aminopyridine quaternary ammonium salt [ Bz-4-NH ]2Py]2[SbBr5](ii) a The yield was 85.6%.
Subjecting the obtained material to infrared spectrum detection, IR (cm)-1): ν(C-H): 3050，ν(C=C)：1646、1529，ν(CH2)：1455，ν(C–N)：1204、1169。
The obtained material is subjected to solid ultraviolet absorption spectrum detection, the spectrum is shown in figure 5, the absorption cut-off wavelengths are 470nm respectively, the corresponding optical band gaps are 2.54eV respectively, the material has certain absorption capacity on visible light, the band gaps belong to the range of typical semiconductor materials, and the material is a potential optical material corresponding to the values of other brominated metal compounds researched as potential solar energy absorbents.
The resulting material was subjected to X-ray single crystal diffraction, and the crystallographic data are shown in Table 1, the crystal structure is shown in FIG. 3, and the unit cell packing is shown in FIG. 4.
The obtained material is subjected to fluorescence analysis, a photoluminescence spectrum is shown in figure 7, under the excitation wavelength of 400nm, the brominated antimonate shows two orange-red emission peaks between 580 and 750nm, and the maximum absorption peaks are respectively at 607nm and 684 nm.
The obtained material can emit obvious orange red light when the luminescent property detection is carried out under the irradiation of 365nm ultraviolet light, as shown in figure 8.
Table 1 main crystallographic data for antimonate bromides of examples 1 and 2 of the invention
Example 3:
the novel pentabromoantimonate benzylpyridinium luminescent material of the embodiment 1 is applied to the preparation of a luminescent film, and comprises the following steps:
weighing 0.8g of polyethylene oxide (PEO) to dissolve in 10g of acetonitrile, and placing the mixture on a magnetic stirrer to be stirred and dissolved at 70 ℃; weighing 0.3g of the novel pentabromoantimonate benzylpyridinium bromide luminescent material in the embodiment 1, and dissolving the novel pentabromoantimonate benzylpyridinium bromide luminescent material in 1g of acetonitrile; mixing the two solutions, stirring at a constant temperature of 70 ℃ until the two solutions are completely dissolved, turning off heating, and slowly stirring at a normal temperature until defoaming is realized until a uniform spinning solution is formed. The prepared spinning solution was injected into a 10mL syringe and spun by an electrostatic spinning machine. Spinning parameters are as follows: the speed is 2.0 mL/h; the needle pitch collector is 9 cm; the voltage is 18 kV; the speed of the collecting drum was 236 revolutions per minute; the spinning time is 8 hours; ambient temperature is 25 ℃; the relative humidity was 50%. Finally, a luminescent film is prepared under the electrostatic spinning condition, and the luminescent performance of the obtained luminescent film is detected under the irradiation of 365nm ultraviolet light, so that the luminescent film can emit obvious orange red light, as shown in figure 9.
Example 4:
the novel luminescent material of benzyl pentabromoantimonate-4-aminopyridine salt in the embodiment 2 is applied to the preparation of a luminescent film, and comprises the following steps:
weighing 0.8g of polyethylene oxide (PEO) to dissolve in 10g of acetonitrile, and placing the mixture on a magnetic stirrer to be stirred and dissolved at 70 ℃; weighing 0.3g of the novel pentabromoantimonate benzyl-4-aminopyridine salt luminescent material obtained in the embodiment 2, and dissolving the novel pentabromoantimonate benzyl-4-aminopyridine salt luminescent material in 1g of acetonitrile; mixing the two solutions, stirring at a constant temperature of 70 ℃ until the two solutions are completely dissolved, turning off heating, and slowly stirring at a normal temperature until defoaming is realized until a uniform spinning solution is formed. The prepared spinning solution was injected into a 10mL syringe and spun by an electrostatic spinning machine. Spinning parameters are as follows: the speed is 2.0 mL/h; the needle pitch collector is 9 cm; the voltage is 18 kV; the speed of the collecting drum was 236 revolutions per minute; the spinning time is 8 hours; ambient temperature is 25 ℃; the relative humidity was 50%. Finally, a luminescent film is prepared under the electrostatic spinning condition, and the luminescent performance of the obtained luminescent film is detected under the irradiation of 365nm ultraviolet light, so that the luminescent film can emit obvious orange red light, as shown in figure 9.
The above embodiments are merely illustrative of the present invention and are not intended to limit the scope of the present invention, and it should be understood that various modifications and other embodiments can be made by those skilled in the art without inventive changes and modifications, which fall within the scope of the present invention. Therefore, the protection scope of the present patent shall be subject to the appended claims.
Claims (10)
1. The novel luminous antimonite bromide material is characterized in that: the chemical structure is shown as the following formula:
2. The novel brominated antimonate luminescent material according to claim 1, wherein: r is H or NH2。
3. The novel brominated antimonate luminescent material according to claim 2, wherein: the novel luminous material of the antimonous bromide is a crystal material, the crystal system is Monoclinic, and the space group isP21/n。
4. The novel brominated antimonate luminescent material according to claim 3, wherein: when R is H, the crystal material has unit cell parameters ofa=10.025-10.028 Å、b=24.191-24.197 Å、c=11.885-11.889 Å，β=105.361-105.369 °; when R is NH2When the crystal material has a unit cell parameter ofa=9.321-9.322 Å、b=12.621-12.622 Å、c=24.958-24.961 Å，β=99.665-99.667°。
5. A method for preparing a novel brominated antimonate luminescent material according to any one of claims 1 to 4, which comprises the following steps:
(1) placing a certain amount of benzyl bromide and substituted pyridinium in a container, adding a solvent for dissolving, heating for reaction, and then concentrating and drying to obtain an oily substance;
(2) a certain amount of Sb2O3Dissolving in hydrobromic acid, adding a certain amount of oily substance obtained in the step 1, heating for reaction, filtering, and concentrating the obtained filtrate to obtain crystals.
6. The method of claim 5, wherein: the solvent in the step (1) is methanol, the reaction condition is that the mixture is stirred and refluxed for 16 to 24 hours at the temperature of 65 to 70 ℃, and the concentration is rotary evaporation; the reaction condition in the step (2) is that the mixture is stirred and heated for 0.5 to 2 hours at the temperature of between 60 and 120 ℃, and the concentration condition of the filtrate is room temperature evaporation.
7. The method of claim 5, wherein: when R is H, the reaction conditions in the step (2) are that stirring and heating are carried out at the temperature of 100 ℃ and 120 ℃ for 0.5-2 hours; when R is NH2In the step (2), a proper amount of methanol is added before the reaction, and the reaction condition is that the mixture is stirred and heated for 0.5 to 2 hours at the temperature of between 60 and 70 ℃.
8. The method of claim 5, wherein: the molar ratio of the benzyl bromide to the substituted pyridinium salt used was 1: (0.5-1.5), Sb used2O3And the mass ratio of the oil is 1: (1.7-1.9).
9. The novel luminous antimonite film is prepared by the following steps: dissolving a certain amount of polyethylene oxide in acetonitrile, and then adding a certain amount of the novel antimonate bromide luminescent material according to any one of claims 1 to 4 for dissolving to form a homogeneous spinning solution; spinning the obtained spinning solution by adopting an electrostatic spinning process to obtain a luminescent film; the mass ratio of the polyethylene oxide to the novel brominated antimonate luminescent material is (2-3): 1.
10. The novel brominated antimonate luminescent film according to claim 9, wherein the parameters of the electrospinning process are as follows: the speed is 2.0 mL/h; the needle pitch collector is 9 cm; the voltage is 18 kV; the speed of the collecting drum was 236 revolutions per minute; the spinning time is 8 hours; ambient temperature is 25 ℃; the relative humidity is 40-70%.
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| CN115057812A (en) * | 2022-07-11 | 2022-09-16 | 华南农业大学 | Tetrachloromanganese composite quaternary ammonium salt, fiber film material and preparation method thereof |
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| JPH0196169A (en) * | 1987-10-09 | 1989-04-14 | Nippon Paint Co Ltd | Novel benzylpyridinum salt |
| CN108129385A (en) * | 2018-01-23 | 2018-06-08 | 华南农业大学 | A kind of compound quaternary ammonium salt nonlinear optics crystalline state material and preparation method thereof |
| CN109761887A (en) * | 2019-01-29 | 2019-05-17 | 华南农业大学 | Degradation of organic dyes catalyst, composite catalyzing material and preparation method thereof |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0196169A (en) * | 1987-10-09 | 1989-04-14 | Nippon Paint Co Ltd | Novel benzylpyridinum salt |
| CN108129385A (en) * | 2018-01-23 | 2018-06-08 | 华南农业大学 | A kind of compound quaternary ammonium salt nonlinear optics crystalline state material and preparation method thereof |
| CN109761887A (en) * | 2019-01-29 | 2019-05-17 | 华南农业大学 | Degradation of organic dyes catalyst, composite catalyzing material and preparation method thereof |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115057812A (en) * | 2022-07-11 | 2022-09-16 | 华南农业大学 | Tetrachloromanganese composite quaternary ammonium salt, fiber film material and preparation method thereof |
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