CN108676555B - Europium-containing ionic liquid red light material, and preparation method and application thereof - Google Patents
Europium-containing ionic liquid red light material, and preparation method and application thereof Download PDFInfo
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Abstract
A preparation method of europium-containing ionic liquid red light material and application thereof in photoluminescence material. The chemical formula of the ionic liquid compound is [ bmim][Eu(HFDK)4]Wherein bmim is 1-butyl-4-methylimidazole, and HFDK is 6,6,7,7,8,8, 8-heptafluoro-2, 2-dimethyloctane-3, 5-dione. The molecular weight is 1471.90, and the molecular weight belongs to monoclinic system with space group ofP2(1) c, unit cell parameter ofa=10.714(2)Å，b=21.902(4)Å，c=26.285(5)Å，alpha=90o，beta=100.80(3)o，gamma=90o，V＝6059(2)Å3And Z is 4. The preparation method adopts a one-pot method, and takes a water-ethanol mixed solvent as a solvent. Colorless massive crystals at room temperature and a melting point of 98.0oC, freezing point of 73.5oC. Under the excitation of ultraviolet light and near ultraviolet light, strong red light is displayed, and the fluorescence lifetime is 0.73 ms (lambda ex =334, lambda em =612 nm). The invention also discloses a preparation method.
Description
Technical Field
The invention belongs to the preparation and application research of ionic liquid, and particularly relates to a beta-diketone europium-containing ionic liquid compound.
The invention also relates to a method for preparing the europium-containing ionic liquid.
The invention also relates to application of the europium-containing ionic liquid.
Background
The ionic liquid is composed of anions and cations, and has a melting point of less than 100oC, molten salt. The solvent has the characteristics of small vapor pressure, wide electrochemical window, no (low) toxicity, incombustibility and the like, and is considered as a green solvent; since ionic liquids are composed of anions and cations, their physicochemical properties can be adjusted by selective combinations of anions and cations, and are therefore also referred to as "tailorable" solvents. Organic synthesis and electricity of ionic liquidThe method has wide practical and potential application prospects in the fields of chemistry, optics and the like.
Currently, ionic liquid is mainly used as a novel green solvent for replacing traditional organic molecular solvents, but the advantages of the ionic liquid are far from being fully exerted. Most ionic liquid compounds are colorless and transparent, and are suitable for the optical field. In addition, because some anions have coordination capacity, a novel ionic liquid compound containing rare earth ions can be obtained by introducing rare earth ions into the ionic liquid and forming coordination anions with the original anions. The introduction of rare earth ions enables the ionic liquid to not only have many advantages of traditional ionic liquid compounds, but also be endowed with properties of rare earth ions, such as luminescence, magnetism, catalytic properties and the like.
The rare earth luminescent material has the advantages of narrow spectral line, pure chromaticity and the like, but the 4f-4f transition of trivalent rare earth ions is forbidden, the light absorption coefficient is small, and the absorption and emission spectral intensity is weak, and the weakness can be overcome by introducing a ligand with a conjugated structure. The beta-diketone ligand has stronger coordination ability with rare earth ions, large light absorption coefficient and high energy transfer efficiency, and is an ideal ligand for preparing high-performance photoluminescent materials. 6,6,7,7,8,8, 8-heptafluoro-2, 2-dimethyloctane-3, 5-dione is an unsymmetrical fluoro β -diketone ligand. The asymmetric beta-diketone ligand can effectively reduce the melting point of the obtained ionic liquid compound, and meanwhile, the fluoro group can effectively reduce energy loss caused by high-frequency vibration (N-H, O-H, C-H and the like). Therefore, the invention hopes that a novel europium-containing ion liquid compound is constructed by using 6,6,7,7,8,8, 8-heptafluoro-2, 2-dimethyloctane-3, 5-diketone as a ligand, europium ions and 1-butyl-4-methylimidazole cations and is used for photoluminescence research. The research on the aspect is not reported in the literature.
Disclosure of Invention
The invention aims to prepare a liquid compound material containing europium ions and having excellent photoluminescence performance.
In order to achieve the purpose, the invention provides an europium-containing ionic liquid compound, the chemical expression of which is [ bmim][Eu(HFDK)4]Which isWherein bmim is 1-butyl-4-methylimidazole, and HFDK is 6,6,7,7,8,8, 8-heptafluoro-2, 2-dimethyloctane-3, 5-dione.
The europium-containing ionic liquid has the single crystal cell parameters as follows: monoclinic system, space group ofP2(1)c， a=10.714(2)Å，b=21.902(4)Å，c= 26.285(5)Å，alpha = 90o，beta = 100.80(3)o，gamma = 90o，V＝6059(2)Å3，Z＝4。
The ionic liquid compound consists of anions and cations, wherein the cation is 1-butyl-4-methylimidazole cation, and the anion is [ Eu (HFDK)4]-Coordinating anions. The Eu (III) ion in the anion is at the center and forms an inverse quadrangular coordination configuration with 8 oxygen atoms of four HFDK ligands.
The method for preparing the ionic liquid adopts a one-pot method, takes 6,6,7,7,8,8, 8-heptafluoro-2, 2-dimethyloctane-3, 5-diketone, europium chloride hexahydrate and 1-butyl-4-methylimidazole chloride as raw materials, takes a water-ethanol mixed solvent as a solvent, and is carried out in a reaction condition of 50-60oC, stirring for 30min, cooling to room temperature to precipitate colorless blocky crystals, and filtering.
The europium-containing ionic liquid provided by the invention can be used as a red light luminescent material.
The europium-containing ionic liquid material is insensitive to water and air, and thermogravimetric and powder diffraction tests show that the europium-containing ionic liquid has better thermal stability. Melting point of 98.0oC, freezing point of 73.5oC。
The photoluminescence performance test shows that the europium-containing ionic liquid shows strong red under the excitation of light of 334nm, which indicates that the material can be used as a photoluminescence 'soft material' and has good application prospect in the field of luminescent materials.
Drawings
FIG. 1 europium-containing ionic liquid [ C ] of the present invention4mim][Eu(HFDK)4]Room temperature and 77K solid state emission spectra.
FIG. 2 shows an europium-containing ionic liquid [ C ] of the present invention4mim][Eu(HFDK)4]CIE coordinate diagram of (a).
Detailed Description
The europium-containing ionic liquid compound (C) obtained by the invention48H55EuF28N2O8) Molecular weight of 1471.90, belonging to monoclinic system, space group ofP2(1) c, single crystal cell parameters ofa=10.714(2)Å，b=21.902(4)Å，c= 26.285(5)Å，alpha = 90o，beta = 100.80(3)o，gamma = 90o，V＝6059(2)Å3，Z＝4。
The central europium ion in the europium-containing ionic liquid compound is in 8 coordination and is chelated and coordinated with 4 HFDK ligands to form a reverse quadrangular coordination configuration.
The europium-containing ionic liquid is prepared in an ethanol-water mixed solvent: bmimCl (0.1747 g, 1 mmol), 6,6,7,7,8,8, 8-heptafluoro-2, 2-dimethyloctane-3, 5-dione (HHFDK, 1.1847 g, 4 mmol), 4mL of 1M aqueous NaOH (4 mmol) were added to 6mL of ethanol, stirred and the temperature was raised to 50%oC, until all is dissolved. Europium chloride hexahydrate (0.3664 g, 1 mmol) is weighed and dissolved in 2mL of water, the solution is added dropwise, stirring is continued for 30min to obtain clear solution, stirring is stopped, and cooling is carried out to room temperature to obtain colorless blocky crystals.
The europium-containing ionic liquid material is insensitive to water and air, and thermogravimetric and powder diffraction tests show that the europium-containing ionic liquid has better thermal stability.
Example 1
bmimCl (0.1747 g, 1 mmol), 6,6,7,7,8,8, 8-heptafluoro-2, 2-dimethyloctane-3, 5-dione (HHFDK, 1.1847 g, 4 mmol), 4mL of 1M aqueous NaOH (4 mmol) were added to 6mL of ethanol, stirred and the temperature was raised to 50%oC, until all is dissolved. Europium chloride hexahydrate (0.3664 g, 1 mmol) is weighed and dissolved in 2mL of water, the solution is added dropwise, stirring is continued for 30min to obtain clear solution, stirring is stopped, and cooling is carried out to room temperature to obtain colorless blocky crystals.
Example 2
bmimCl (0.1747 g, 1 mmol), 6,6,7,7,8,8, 8-heptafluoro-2, 2-dimethyloctane-3, 5-dione (HHFDK, 1.1847 g, 4 mmol), 4mL of 1M aqueous NaOH (4 mmol) and 6mL of EtOHIn alcohol, stirring and raising the temperature to 60 deg.CoC, until all is dissolved. Europium chloride hexahydrate (0.3664 g, 1 mmol) is weighed and added into the solution, stirring is continued for 30min to obtain clear solution, stirring is stopped, and cooling is carried out to room temperature to obtain colorless massive crystals.
Example 3
bmimCl (0.1747 g, 1 mmol), 6,6,7,7,8,8, 8-heptafluoro-2, 2-dimethyloctane-3, 5-dione (HHFDK, 1.1847 g, 4 mmol), NaOH (0.1600 g, 4 mmol) in water was added to 10mL of an ethanol-water mixed solvent (v/v =3: 2), stirred and the temperature was raised to 60%oC, until a clear solution is obtained. Europium chloride hexahydrate (0.3664 g, 1 mmol) is weighed and added into the solution, stirring is continued for 30min to obtain clear solution, stirring is stopped, and cooling is carried out to room temperature to obtain colorless blocky crystals.
Example 4
Photoluminescence performance:
at 298K, when excited by 334nm excitation light, the ionic liquid compound shows a characteristic red color of Eu (III), and the emission wavelength is: 587.75, 593.50, 612.00, 615.75, 650.25, 656.00, 701.00nm, having CIE coordinates: 0.577, 0.328. The room temperature solid state emission spectrum and the CIE coordinate diagram are respectively shown in figure 1 and figure 2.
Example 5
Photoluminescence performance:
at 77K, when excited by 334nm excitation light, the europium-containing ionic liquid compound shows a typical red color, and the emission wavelength is: 579.50, 585.50, 588.75, 593.50, 595.25, 612.25, 616.50, 619.50, 623.25, 634.50, 651.00, 656.25, 673.25, 690.00, 692.50, 696.00, 701.00nm with CIE coordinates: 0.610, 0.335. The low-temperature solid-state emission spectrum and the CIE coordinate diagram are respectively shown in figure 1 and figure 2.
Claims (6)
1. A europium-containing ionic liquid red light material is characterized by having a chemical formula as follows: [ bmim][Eu(HFDK)4]Wherein bmim is 1-butyl-4-methylimidazole, and HFDK is 6,6,7,7,8,8, 8-heptafluoro-2, 2-dimethyloctane-3, 5-dione;
monoclinic system, space group ofP2(1) c, single crystal cell parametersIs composed ofa=10.714(2)Å，b=21.902(4)Å，c= 26.285(5)Å，alpha = 90o，beta = 100.80(3)o，gamma = 90o，V＝6059(2)Å3，Z＝4；
The preparation method of the material comprises the following steps: the preparation method is characterized by adopting a one-pot method, taking 6,6,7,7,8,8, 8-heptafluoro-2, 2-dimethyloctane-3, 5-diketone, europium chloride hexahydrate and 1-butyl-4-methylimidazole chloride as raw materials, taking a water-ethanol mixed solvent as a solvent, stirring for 30min at the temperature of 50-60 ℃, cooling to room temperature to precipitate colorless blocky crystals, and filtering.
2. The europium-containing ionic liquid red light material of claim 1, wherein: the molar ratio of 6,6,7,7,8,8, 8-heptafluoro-2, 2-dimethyloctane-3, 5-dione, europium chloride hexahydrate and 1-butyl-4-methylimidazole chloride is as follows: 4:1:1.
3. The europium-containing ionic liquid red light material of claim 1, wherein: the material is colorless massive crystals at room temperature, the melting point is 98.0 ℃, and the freezing point is 73.5 ℃.
4. The europium-containing ionic liquid red light material of claim 1, wherein: under ultraviolet and near ultraviolet excitation, the material shows Eu (III) characteristic red.
5. The europium-containing ionic liquid red light material of claim 1, wherein: the emission wavelength of the material at 298K is as follows: 587.75, 593.50, 612.00, 615.75, 650.25, 656.00, 701.00nm, with CIE coordinates: 0.577, 0.328; emission wavelength at 77K is: 579.50, 585.50, 588.75, 593.50, 595.25, 612.25, 616.50, 619.50, 623.25, 634.50, 651.00, 656.25, 673.25, 690.00, 692.50, 696.00, 701.00nm, with CIE coordinates: 0.610,0.335.
6. The use of the europium-containing ionic liquid red light material of claim 1, wherein: the material can be used as a red light emitting material.
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