CN108676555A - One kind red light material of liquid containing europium ion and preparation method and application - Google Patents
One kind red light material of liquid containing europium ion and preparation method and application Download PDFInfo
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- CN108676555A CN108676555A CN201810518522.9A CN201810518522A CN108676555A CN 108676555 A CN108676555 A CN 108676555A CN 201810518522 A CN201810518522 A CN 201810518522A CN 108676555 A CN108676555 A CN 108676555A
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/77—Preparation of chelates of aldehydes or ketones
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- C07C49/04—Saturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/16—Saturated compounds containing keto groups bound to acyclic carbon atoms containing halogen
- C07C49/167—Saturated compounds containing keto groups bound to acyclic carbon atoms containing halogen containing only fluorine as halogen
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- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C07D233/58—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring nitrogen atoms
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
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- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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Abstract
A kind of preparation of the red light material of liquid containing europium ion and its application in terms of embedded photoluminescent material.The chemical formula of the ion liquid compound is [bmim] [Eu (HFDK)4], wherein bmim is 1 butyl, 4 methylimidazole, 6,6,7,7,8,8,8 seven fluorine of HFDK, 2,2 dimethyl octane, 3,5 diketone.Its molecular weight is 1471.90, belongs to monoclinic system, and space group isP2 (1) c, cell parameter area=10.714 (2),b=21.902 (4),c=26.285 (5), alpha=90o, beta=100.80 (3)o, gamma=90o, V=6059 (2)3, Z=4.It is prepared using one kettle way, using water-ethanol mixed solvent as solvent.It is colourless bulk crystals, fusing point 98.0 at room temperatureoC, solidification point 73.5oC.Under ultraviolet and near ultraviolet excitation, show that very strong red light, fluorescence lifetime are 0.73 ms (λ ex=334, λ em=612 nm).The invention also discloses preparation methods.
Description
Technical field
The invention belongs to the preparation and application of ionic liquid researchs, and in particular to a kind of beta-diketon class fluidization containing europium ion
Close object.
The invention further relates to a kind of methods preparing the above-mentioned liquid containing europium ion.
The invention further relates to the applications of the above-mentioned liquid containing europium ion.
Background technology
Ionic liquid is that one kind is made of zwitterion, and fusing point is less than 100oThe fused salt of C.It is small with vapour pressure, electrochemical
Learn that window is wide, nothing（It is low）A kind of the features such as malicious, non-combustible, it is considered to be green solvent；Since ionic liquid is by zwitterion group
At being combined by the selectivity of zwitterion, its physicochemical properties be adjusted, therefore solvent " also referred to as can be designed ".From
Sub- liquid has extensive reality and potential application foreground in fields such as organic synthesis, electrochemistry, optics.
Current ionic liquid is primarily as a kind of novel green solvent substituting traditional organic molecular solvents, but this is much
Not the advantages of not giving full play to ionic liquid.Most ion liquid compounds are water white transparencies, compare and are led suitable for optics
Domain.Further, since some anion have coordination ability, it is and original by introducing a kind of rare earth ion into ionic liquid
Anion forms coordination anion, can obtain a kind of novel ion liquid compound containing rare earth ion.Rare earth ion
It introduces so that ionic liquid not only has many advantages, such as conventional ion liquid compound, but also has been assigned the property of rare earth ion
Can, such as luminous, magnetism, catalytic performance etc..
Rare earth luminescent material has many advantages, such as that spectral line is narrow, coloration is pure, but the 4f-4f transition of trivalent rare earth ions is to prohibit
, absorptivity is small, and Absorption and emission spectra intensity is weak, this can be overcome weak by introducing ligand with a conjugated structure
Point.Beta-diketonate ligand has stronger and rare-earth ion coordination ability, and absorptivity is big, and energy transfer efficiency is high, is more to manage
The ligand for the preparation high-performance optical electroluminescent material thought.Seven fluoro- 2,2- dimethyl octane -3,5- diketone of 6,6,7,7,8,8,8- is
A kind of asymmetric fluoro beta-diketonate ligand.Gained ionic liquid chemical combination can effectively be reduced using asymmetric beta-diketonate ligand
The fusing point of object, while fluoro can effectively reduce high-frequency vibration（N-H, O-H, C-H etc.）Caused energy loss.Therefore,
The present invention wish by with 6,6,7,7,8,8,8- seven fluoro- 2,2- dimethyl octane -3,5- diketone be ligand, with europium ion and 1-
Butyl -4-methylimidazole cation constructs novel liquid compound containing europium ion, is studied for luminescence generated by light.Related this respect
Research is there is not yet document report.
Invention content
It is an object of the invention to prepare a kind of material of liquid compound containing europium ion with excellent photoluminescence performance
Material.
To achieve the above object, liquid compound containing europium ion provided by the present invention, chemical expression are [bmim]
[Eu(HFDK)4], wherein bmim is 1- butyl -4-methylimidazole, 6,6,7,7,8,8,8- seven fluoro- 2,2- dimethyl-octas of HFDK
Alkane -3,5- diketone.
The liquid containing europium ion, monocrystalline cell parameter are：Monoclinic system, space group areP2 (1) c, a=10.714
(2),b=21.902 (4),c=26.285 (5), alpha=90o, beta=100.80 (3)o, gamma=90o, V=
6059(2)Å3, Z=4.
The ion liquid compound is made of zwitterion, and cation is 1- butyl -4-methylimidazole cation, anion
For [Eu (HFDK)4]-Coordination anion.Eu (III) ion is in center in anion, 8 oxygen atoms with four HFDK ligands
Form anti-quadrangular coordination configuration.
The method provided by the invention for preparing above-mentioned ionic liquid, is prepared using one kettle way, with 6,6,7,7,8,8,8- seven
Fluoro- 2,2- dimethyl octane -3,5- diketone, six chloride hydrate europiums and chlorination 1- butyl -4-methylimidazole are raw material, with water-second
Alcohol mixed solvent is solvent, in 50-60oC stirs 30min, is cooled to room temperature, that is, colourless bulk crystals are precipitated, and filters.
Liquid containing europium ion provided by the invention can be used as a kind of red emitting material.
It is insensitive to water and air that this contains europium ion fluent material, and thermogravimetric and powder diffraction test show that this contains europium ion
Liquid has preferable thermal stability.Fusing point is 98.0oC, solidification point 73.5oC。
Photoluminescence performance test shows that this contains europium ion liquid and shows very strong red under the excitation of 334nm light, indicates
A kind of luminescence generated by light " soft material " can be used as by the material, have good application prospect in field of light emitting materials.
Description of the drawings
[the C of liquid containing europium ion of Fig. 1 present invention4mim][Eu(HFDK)4] room temperature and 77K solid-state launching light spectrograms.
[the C of liquid containing europium ion of Fig. 2 present invention4mim][Eu(HFDK)4] CIE coordinate diagrams.
Specific implementation mode
The obtained liquid compound containing europium ion of the present invention（C48H55EuF28N2O8）, molecular weight 1471.90, category monocline
Crystallographic system, space group areP2 (1) c, monocrystalline cell parameter area=10.714 (2),b=21.902 (4),c=26.285 (5),
alpha = 90o, beta=100.80 (3)o, gamma=90o, V=6059 (2)3, Z=4.
It is 8 coordinations that this, which contains center europium ion in europium ion liquid compound, is coordinated with 4 HFDK ligand sequestrations, is formed anti-
Quadrangular coordination configuration.
This contains europium ion liquid and is prepared in ethanol-water mixed solvent：By bmimCl (0.1747 g, 1 mmol), 6,
Seven fluoro- 2,2- dimethyl octane -3,5- diketone of 6,7,7,8,8,8-（HHFDK, 1.1847 g, 4 mmol）, 4mL 1M NaOH
（4mmol）Aqueous solution is added in 6mL ethyl alcohol, stirs and increases temperature to 50oC, until all dissolvings.Weigh six chloride hydrates
Europium（0.3664 g, 1 mmol）It is dissolved in 2mL water, is added dropwise in above-mentioned solution, continue to stir 30 min, obtain clear solution,
Stop stirring, is cooled to room temperature, obtains colourless bulk crystals.
It is insensitive to water and air that this contains europium ion fluent material, and thermogravimetric and powder diffraction test show that this contains europium ion
Liquid has preferable thermal stability.
Example 1
BmimCl (0.1747 g, 1 mmol), 6,6,7,7,8,8,8- seven fluoro- 2,2- dimethyl octane -3,5- diketone
（HHFDK, 1.1847 g, 4 mmol）, 4mL 1M NaOH（4mmol）Aqueous solution is added in 6mL ethyl alcohol, stirs and increases temperature
It spends to 50oC, until all dissolvings.Weigh six chloride hydrate europiums（0.3664 g, 1 mmol）It is dissolved in 2mL water, is added dropwise
In above-mentioned solution, continues to stir 30 min, obtain clear solution, stop stirring, be cooled to room temperature, obtain colourless bulk crystals.
Example 2
BmimCl (0.1747 g, 1 mmol), 6,6,7,7,8,8,8- seven fluoro- 2,2- dimethyl octane -3,5- diketone
（HHFDK, 1.1847 g, 4 mmol）, 4mL 1M NaOH（4mmol）Aqueous solution is added in 6mL ethyl alcohol, stirs and increases temperature
It spends to 60oC, until all dissolvings.Weigh six chloride hydrate europiums（0.3664 g, 1 mmol）It is added in above-mentioned solution, continues
30 min are stirred, clear solution is obtained, stops stirring, is cooled to room temperature, obtains colourless bulk crystals.
Example 3
BmimCl (0.1747 g, 1 mmol), 6,6,7,7,8,8,8- seven fluoro- 2,2- dimethyl octane -3,5- diketone
（HHFDK, 1.1847 g, 4 mmol）, NaOH（0.1600 g, 4mmol）10mL ethanol-water mixed solvents are added in aqueous solution
In（v/v=3:2）, stir and increase temperature to 60oC, until obtaining clear solution.Weigh six chloride hydrate europiums（0.3664 g,
1 mmol is added in above-mentioned solution, continues to stir 30 min, obtains clear solution, stops stirring, be cooled to room temperature, obtain no color lump
Shape crystal.
Example 4
Photoluminescence performance：
In 298 K, with 334nm excitations, which shows that the feature of Eu (III) is red, transmitted wave
It is a length of：587.75,593.50,612.00,615.75,650.25,656.00,701.00 nm, CIE coordinate is：
0.577, 0.328.Its room temperature solid launching light spectrogram and CIE coordinate diagrams are shown in Fig. 1 and Fig. 2 respectively.
Example 5
Photoluminescence performance：
In 77 K, with 334nm excitations, this contains europium ion liquid compound and shows that typical red, launch wavelength are：
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, CIE coordinate
For：0.610, 0.335.Its low temperature solid-state launching light spectrogram and CIE coordinate diagrams are shown in Fig. 1 and Fig. 2 respectively.
Claims (8)
1. a kind of red light material of liquid containing europium ion, it is characterised in that its chemical formula is：[bmim][Eu(HFDK)4], wherein
Bmim is 1- butyl -4-methylimidazole, 6,6,7,7,8,8,8- seven fluoro- 2,2- dimethyl octane -3,5- diketone of HFDK.
2. liquid compound containing europium ion as described in claim 1, it is characterised in that its monocrystalline cell parameter is：Monoclinic crystal
System, space group areP2 (1) c, monocrystalline cell parameter area=10.714 (2),b=21.902 (4),c=26.285 (5), alpha
= 90o, beta=100.80 (3)o, gamma=90o, V=6059 (2)3, Z=4.
3. the preparation method of the liquid compound containing europium ion as described in claim 1, it is characterised in that：Using one kettle way system
It is standby, with 6,6,7,7,8,8,8- seven fluoro- 2,2- dimethyl octane -3,5- diketone, six chloride hydrate europiums and chlorination 1- butyl -4- first
Base imidazoles is raw material, using water-ethanol mixed solvent as solvent, in 50-60oC stirs 30min, is cooled to room temperature and is precipitated without color lump
Shape crystal, filtering.
4. preparation method as claimed in claim 3, it is characterised in that：Seven fluoro- 2,2- dimethyl octanes-of 6,6,7,7,8,8,8-
The molar ratio of 3,5- diketone, six chloride hydrate europiums and chlorination 1- butyl -4-methylimidazole is：4:1:1.
5. the physical property of the liquid compound containing europium ion as described in claim 1, it is characterised in that：It is colourless at room temperature
Bulk crystals, fusing point 98.0oC, solidification point 73.5oC。
6. the photoluminescence performance of the liquid compound containing europium ion as described in claim 1, it is characterised in that：Ultraviolet and close
Under ultraviolet excitation, which shows very strong Eu (III) feature red.
7.298K when launch wavelength be：587.75, 593.50, 612.00, 615.75, 650.25, 656.00, 701.00
Nm, CIE coordinate is：0.577, 0.328；Launch wavelength is when 77K：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, CIE coordinate is：0.610, 0.335.
8. the purposes of the liquid compound containing europium ion as described in claim 1, it is characterised in that：The material may be used as red
Luminescent material.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109705846A (en) * | 2018-12-10 | 2019-05-03 | 青岛农业大学 | A kind of ion type perfluoro polymer red light material and preparation method and application |
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| CN109705846A (en) * | 2018-12-10 | 2019-05-03 | 青岛农业大学 | A kind of ion type perfluoro polymer red light material and preparation method and application |
| CN109705846B (en) * | 2018-12-10 | 2021-09-28 | 青岛农业大学 | Ionic perfluoropolymer red-light material and preparation method and application thereof |
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