CN108676555B - A kind of europium-containing ionic liquid red light material and preparation method and application - Google Patents
A kind of europium-containing ionic liquid red light material and preparation method and application Download PDFInfo
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- 239000002608 ionic liquid Substances 0.000 title claims abstract description 43
- 229910052693 Europium Inorganic materials 0.000 title claims abstract description 29
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 title claims abstract description 27
- 239000000463 material Substances 0.000 title claims abstract description 23
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- SQNZLBOJCWQLGQ-UHFFFAOYSA-N 6,6,7,7,8,8,8-heptafluoro-2,2-dimethyloctane-3,5-dione Chemical group CC(C)(C)C(=O)CC(=O)C(F)(F)C(F)(F)C(F)(F)F SQNZLBOJCWQLGQ-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000013078 crystal Substances 0.000 claims abstract description 9
- 239000002904 solvent Substances 0.000 claims abstract description 7
- IQQRAVYLUAZUGX-UHFFFAOYSA-N 1-butyl-3-methylimidazolium Chemical compound CCCCN1C=C[N+](C)=C1 IQQRAVYLUAZUGX-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000000034 method Methods 0.000 claims abstract description 6
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 claims abstract description 5
- 230000005284 excitation Effects 0.000 claims abstract description 5
- 238000002844 melting Methods 0.000 claims abstract description 5
- 230000008018 melting Effects 0.000 claims abstract description 5
- 239000012046 mixed solvent Substances 0.000 claims abstract description 5
- 239000000126 substance Substances 0.000 claims abstract description 4
- AEMJJEJBDDKEPC-UHFFFAOYSA-N 1-butyl-4-methylimidazole Chemical group CCCCN1C=NC(C)=C1 AEMJJEJBDDKEPC-UHFFFAOYSA-N 0.000 claims abstract description 3
- 238000007710 freezing Methods 0.000 claims abstract description 3
- 230000008014 freezing Effects 0.000 claims abstract description 3
- 238000005580 one pot reaction Methods 0.000 claims abstract description 3
- 238000003756 stirring Methods 0.000 claims description 9
- AWDWVTKHJOZOBQ-UHFFFAOYSA-K europium(3+);trichloride;hexahydrate Chemical compound O.O.O.O.O.O.[Cl-].[Cl-].[Cl-].[Eu+3] AWDWVTKHJOZOBQ-UHFFFAOYSA-K 0.000 claims description 7
- WLEXDTWHSTZPMH-UHFFFAOYSA-N 3-butyl-5-methyl-1H-imidazol-3-ium chloride Chemical compound [Cl-].C(CCC)[NH+]1C=NC(=C1)C WLEXDTWHSTZPMH-UHFFFAOYSA-N 0.000 claims description 3
- 239000002994 raw material Substances 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims 1
- 210000002858 crystal cell Anatomy 0.000 claims 1
- 238000001914 filtration Methods 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 14
- 238000005424 photoluminescence Methods 0.000 abstract description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 150000001450 anions Chemical class 0.000 description 10
- -1 rare earth ions Chemical class 0.000 description 10
- 239000000243 solution Substances 0.000 description 9
- 239000003446 ligand Substances 0.000 description 7
- 229910052761 rare earth metal Inorganic materials 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 150000001768 cations Chemical class 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000000295 emission spectrum Methods 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 238000010586 diagram Methods 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 1
- 230000005518 electrochemistry Effects 0.000 description 1
- 238000003682 fluorination reaction Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000007779 soft material Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
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Abstract
Description
技术领域technical field
本发明属于离子液体的制备与应用研究，具体涉及一种β-二酮类含铕离子液体化合物。The invention belongs to the research on preparation and application of ionic liquids, in particular to a beta-diketone type europium-containing ionic liquid compound.
本发明还涉及一种制备上述含铕离子液体的方法。The present invention also relates to a method for preparing the above-mentioned europium-containing ionic liquid.
本发明还涉及上述含铕离子液体的应用。The present invention also relates to the application of the above-mentioned europium-containing ionic liquid.
背景技术Background technique
离子液体是一类由阴阳离子组成，且熔点低于100 oC的熔盐。具有蒸汽压小、电化学窗口宽、无（低）毒、不可燃等特点，被认为是一种绿色溶剂；由于离子液体由阴阳离子组成，通过阴阳离子的选择性组合，可调节其物理化学性质，因此也被称为可“设计”溶剂。离子液体在有机合成、电化学、光学等领域有着广泛的实际和潜在应用前景。Ionic liquids are a class of molten salts composed of anions and cations with melting points below 100 oC . It has the characteristics of small vapor pressure, wide electrochemical window, no (low) toxicity, and non-flammability, and is considered to be a green solvent; since ionic liquids are composed of anions and cations, their physical and chemical properties can be adjusted through the selective combination of anions and cations. properties and are therefore also referred to as "designable" solvents. Ionic liquids have a wide range of practical and potential applications in organic synthesis, electrochemistry, optics and other fields.
当前离子液体主要是作为一种替代传统有机分子溶剂的新型绿色溶剂，但这远远没有充分发挥离子液体的优点。多数离子液体化合物是无色透明的，比较适合用于光学领域。此外，由于一些阴离子具有配位能力，通过向离子液体中引入一种稀土离子，与原有的阴离子形成配位阴离子，可以得到一种含有稀土离子的新型离子液体化合物。稀土离子的引入使得离子液体不仅具有传统离子液体化合物的诸多优点，而且被赋予了稀土离子的性能，比如发光、磁性、催化性能等。At present, ionic liquids are mainly used as a new type of green solvent to replace traditional organic molecular solvents, but this is far from giving full play to the advantages of ionic liquids. Most ionic liquid compounds are colorless and transparent, and are more suitable for use in the optical field. In addition, due to the coordination ability of some anions, a new type of ionic liquid compound containing rare earth ions can be obtained by introducing a rare earth ion into the ionic liquid to form a coordination anion with the original anion. The introduction of rare earth ions makes ionic liquids not only have many advantages of traditional ionic liquid compounds, but also endow rare earth ions with properties such as luminescence, magnetic properties, and catalytic properties.
稀土发光材料具有谱线窄、色度纯等优点，但三价稀土离子的4f-4f跃迁是禁阻的，吸光系数小，吸收和发射光谱强度弱，通过引入具有共轭结构的配体可以克服这一弱点。β-二酮配体具有较强的与稀土离子配位能力，吸光系数大，能量传递效率高，是较为理想的制备高性能光致发光材料的配体。6,6,7,7,8,8,8-七氟-2,2-二甲基辛烷-3,5-二酮是一种不对称的氟代β-二酮配体。采用不对称的β-二酮配体可以有效降低所得离子液体化合物的熔点，同时氟代可以有效减少高频振动（N-H, O-H, C-H等）所造成的能量损失。因此，本发明希望通过以6,6,7,7,8,8,8-七氟-2,2-二甲基辛烷-3,5-二酮为配体，与铕离子和1-丁基-4-甲基咪唑阳离子构筑新型含铕离子液体化合物，用于光致发光研究。有关这方面的研究尚未见文献报道。Rare earth luminescent materials have the advantages of narrow spectral lines and pure chromaticity, but the 4f-4f transition of trivalent rare earth ions is forbidden, the absorption coefficient is small, and the absorption and emission spectral intensities are weak. overcome this weakness. β-diketone ligands have strong coordination ability with rare earth ions, large absorption coefficient and high energy transfer efficiency, and are ideal ligands for the preparation of high-performance photoluminescent materials. 6,6,7,7,8,8,8-heptafluoro-2,2-dimethyloctane-3,5-dione is an asymmetric fluoro β-diketone ligand. The use of asymmetric β-diketone ligands can effectively reduce the melting point of the obtained ionic liquid compounds, while fluorination can effectively reduce the energy loss caused by high-frequency vibrations (N-H, O-H, C-H, etc.). Therefore, the present invention hopes that by using 6,6,7,7,8,8,8-heptafluoro-2,2-dimethyloctane-3,5-dione as a ligand, with europium ion and 1- A new type of europium-containing ionic liquid compound was constructed by butyl-4-methylimidazolium cation for photoluminescence research. Research on this aspect has not been reported in the literature.
发明内容SUMMARY OF THE INVENTION
本发明的目的在于制备一种具有优异光致发光性能的的含铕离子液体化合物材料。The object of the present invention is to prepare a europium-containing ionic liquid compound material with excellent photoluminescence properties.
为实现上述目的，本发明所提供的含铕离子液体化合物，其化学表达式为[bmim][Eu(HFDK)4]，其中bmim为1-丁基-4-甲基咪唑，HFDK为6,6,7,7,8,8,8-七氟-2,2-二甲基辛烷-3,5-二酮。In order to achieve the above object, the europium-containing ionic liquid compound provided by the present invention has a chemical expression of [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.
所述的含铕离子液体，其单晶晶胞参数为：单斜晶系，空间群为P2(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 single crystal unit cell parameters of the europium-containing ionic liquid are: monoclinic, space group P 2(1)c, a = 10.714(2) Å, b = 21.902(4) Å, c = 26.285 (5)Å, alpha = 90 o , beta = 100.80(3) o , gamma = 90 o , V=6059(2)Å 3 , Z=4.
该离子液体化合物由阴阳离子组成，阳离子为1-丁基-4-甲基咪唑阳离子，阴离子为[Eu(HFDK)4]-配位阴离子。阴离子中Eu(III)离子处于中心，与四个HFDK配体的8个氧原子形成反四棱柱配位构型。The ionic liquid compound is composed of anions and cations, the cations are 1-butyl-4-methylimidazolium cations, and the anions are [Eu(HFDK) 4 ] -coordination anions. The Eu(III) ion in the anion is in the center and forms an inverse quadrangular prism coordination configuration with the eight oxygen atoms of the four HFDK ligands.
本发明提供的制备上述离子液体的方法，采用一锅法制备，以6,6,7,7,8,8,8-七氟-2,2-二甲基辛烷-3,5-二酮、六水合氯化铕和氯化1-丁基-4-甲基咪唑为原料，以水-乙醇混合溶剂为溶剂，在50-60 oC搅拌30min，冷至室温，即析出无色块状晶体，过滤。The method for preparing the above-mentioned ionic liquid provided by the present invention adopts a one-pot method to prepare, using 6,6,7,7,8,8,8-heptafluoro-2,2-dimethyloctane-3,5-difluoro- Ketone, europium chloride hexahydrate and 1-butyl-4-methylimidazole chloride are used as raw materials, and water-ethanol mixed solvent is used as solvent, stirred at 50-60 o C for 30min, cooled to room temperature, and colorless lumps are precipitated crystals, filtered.
本发明提供的含铕离子液体，可以作为一种红光发光材料。The europium-containing ionic liquid provided by the present invention can be used as a red light emitting material.
该含铕离子液体材料对水和空气不敏感，热重和粉末衍射测试表明，该含铕离子液体具有较好的热稳定性。熔点为98.0 oC，凝固点为73.5 oC。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 good thermal stability. The melting point is 98.0 o C and the freezing point is 73.5 o C.
光致发光性能测试表明，该含铕离子液体在334nm光激发下显示很强的红色，预示着该材料可以作为一种光致发光“软材料”，在发光材料领域具有很好的应用前景。The photoluminescence performance test shows that the europium-containing ionic liquid shows a strong red color under the excitation of 334nm light, indicating that the material can be used as a photoluminescence "soft material" and has a good application prospect in the field of luminescent materials.
附图说明Description of drawings
图1 本发明的含铕离子液体[C4mim][Eu(HFDK)4]的室温和77K固态发射光谱图。Figure 1. Room temperature and 77K solid-state emission spectra of the europium-containing ionic liquid [C 4 mim][Eu(HFDK) 4 ] of the present invention.
图2 本发明的含铕离子液体[C4mim][Eu(HFDK)4]的CIE坐标图。Fig. 2 CIE coordinate diagram of the europium-containing ionic liquid [C 4 mim][Eu(HFDK) 4 ] of the present invention.
具体实施方式Detailed ways
本发明所得到的含铕离子液体化合物（C48H55EuF28N2O8），分子量为1471.90，属单斜晶系，空间群为P2(1)c，单晶晶胞参数为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 europium-containing ionic liquid compound (C 48 H 55 EuF 28 N 2 O 8 ) obtained by the invention has a molecular weight of 1471.90, belongs to the monoclinic system, the space group is P 2(1)c, and the single unit cell parameter is a =10.714(2)Å, b =21.902(4)Å, c = 26.285(5)Å, alpha = 90 o , beta = 100.80(3) o , gamma = 90 o , V=6059(2)Å 3 , Z=4.
该含铕离子液体化合物中中心铕离子为8配位，与4个HFDK配体螯合配位，形成反四棱柱配位构型。The central europium ion in the europium-containing ionic liquid compound is 8-coordinated, which is chelated and coordinated with four HFDK ligands to form an inverse quadrangular prism coordination configuration.
该含铕离子液体在乙醇-水混合溶剂中制备：将bmimCl (0.1747 g, 1 mmol)，6,6,7,7,8,8,8-七氟-2,2-二甲基辛烷-3,5-二酮（HHFDK, 1.1847 g, 4 mmol），4mL 1M NaOH（4mmol）水溶液加入6mL乙醇中，搅拌并升高温度至50 oC，直至全部溶解。称取六水合氯化铕（0.3664 g, 1 mmol）溶于2mL水中，逐滴加入上述溶液中，继续搅拌30 min，得澄清溶液，停止搅拌，冷却至室温，得到无色块状晶体。The europium-containing ionic liquid was 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), 4 mL of 1 M NaOH (4 mmol) in water was added to 6 mL of ethanol, stirred and raised to 50 ° C until all dissolved. Weigh europium chloride hexahydrate (0.3664 g, 1 mmol), dissolve it in 2 mL of water, add dropwise to the above solution, and continue stirring for 30 min to obtain a clear solution, stop stirring, and cool to room temperature to obtain colorless massive crystals.
该含铕离子液体材料对水和空气不敏感，热重和粉末衍射测试表明，该含铕离子液体具有较好的热稳定性。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 good thermal stability.
实例1Example 1
bmimCl (0.1747 g, 1 mmol)，6,6,7,7,8,8,8-七氟-2,2-二甲基辛烷-3,5-二酮（HHFDK, 1.1847 g, 4 mmol），4mL 1M NaOH（4mmol）水溶液加入6mL乙醇中，搅拌并升高温度至50 oC，直至全部溶解。称取六水合氯化铕（0.3664 g, 1 mmol）溶于2mL水中，逐滴加入上述溶液中，继续搅拌30 min，得澄清溶液，停止搅拌，冷却至室温，得到无色块状晶体。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) ), 4 mL of 1 M NaOH (4 mmol) aqueous solution was added to 6 mL of ethanol, stirred and raised to 50 o C until all dissolved. Weigh europium chloride hexahydrate (0.3664 g, 1 mmol), dissolve it in 2 mL of water, add dropwise to the above solution, and continue stirring for 30 min to obtain a clear solution, stop stirring, and cool to room temperature to obtain colorless massive crystals.
实例2Example 2
bmimCl (0.1747 g, 1 mmol)，6,6,7,7,8,8,8-七氟-2,2-二甲基辛烷-3,5-二酮（HHFDK, 1.1847 g, 4 mmol），4mL 1M NaOH（4mmol）水溶液加入6mL乙醇中，搅拌并升高温度至60 oC，直至全部溶解。称取六水合氯化铕（0.3664 g, 1 mmol）加入上述溶液中，继续搅拌30 min，得澄清溶液，停止搅拌，冷却至室温，得到无色块状晶体。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) ), 4 mL of 1 M NaOH (4 mmol) aqueous solution was added to 6 mL of ethanol, stirred and raised to 60 o C until all dissolved. Weigh europium chloride hexahydrate (0.3664 g, 1 mmol) into the above solution, continue stirring for 30 min to obtain a clear solution, stop stirring, and cool to room temperature to obtain colorless bulk crystals.
实例3Example 3
bmimCl (0.1747 g, 1 mmol)，6,6,7,7,8,8,8-七氟-2,2-二甲基辛烷-3,5-二酮（HHFDK, 1.1847 g, 4 mmol），NaOH（0.1600 g, 4mmol）水溶液加入10mL乙醇-水混合溶剂中（v/v=3:2），搅拌并升高温度至60 oC，直至得到澄清溶液。称取六水合氯化铕（0.3664 g,1 mmol加入上述溶液中，继续搅拌30 min，得澄清溶液，停止搅拌，冷却至室温，得到无色块状晶体。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) aqueous solution was added to 10 mL of ethanol-water mixed solvent (v/v=3:2), stirred and raised the temperature to 60 o C until a clear solution was obtained. Weigh europium chloride hexahydrate (0.3664 g, 1 mmol) into the above solution, and continue stirring for 30 min to obtain a clear solution, stop stirring, and cool to room temperature to obtain colorless bulk crystals.
实例4Example 4
光致发光性能：Photoluminescence properties:
在298 K，以334nm激发光激发，该离子液体化合物显示出Eu(III)的特征红色，发射波长为：587.75, 593.50, 612.00, 615.75, 650.25, 656.00, 701.00 nm，其CIE坐标为：0.577, 0.328。其室温固态发射光谱图和CIE坐标图分别见图1 和图2。At 298 K, excited by excitation light of 334 nm, the ionic liquid compound shows the characteristic red color of Eu(III), the emission wavelengths are: 587.75, 593.50, 612.00, 615.75, 650.25, 656.00, 701.00 nm, and its CIE coordinates are: 0.577, 0.328. Its room temperature solid-state emission spectrum and CIE coordinate diagram are shown in Figure 1 and Figure 2, respectively.
实例5Example 5
光致发光性能：Photoluminescence properties:
在77 K，以334nm激发光激发，该含铕离子液体化合物显示出典型的红色，发射波长为：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, 701.00 nm，其CIE坐标为：0.610, 0.335。其低温固态发射光谱图和CIE坐标图分别见图1 和图2。At 77 K, excited by excitation light of 334 nm, the europium-containing ionic liquid compound showed typical red color with emission wavelengths: 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, 701.00 nm, its CIE coordinates are: 0.610, 0.335. Its low-temperature solid-state emission spectrum and CIE coordinates are shown in Figure 1 and Figure 2, respectively.
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