CN116621757A - Preparation method of flexible bidentate ligand PYDE and light conversion agent - Google Patents
Preparation method of flexible bidentate ligand PYDE and light conversion agent Download PDFInfo
- Publication number
- CN116621757A CN116621757A CN202211710262.8A CN202211710262A CN116621757A CN 116621757 A CN116621757 A CN 116621757A CN 202211710262 A CN202211710262 A CN 202211710262A CN 116621757 A CN116621757 A CN 116621757A
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- CN
- China
- Prior art keywords
- pyde
- flexible
- bidentate ligand
- light conversion
- conversion agent
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 238000006243 chemical reaction Methods 0.000 title claims abstract description 22
- 239000003795 chemical substances by application Substances 0.000 title claims abstract description 17
- 239000003446 ligand Substances 0.000 title claims abstract description 17
- 238000002360 preparation method Methods 0.000 title abstract description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 12
- 239000007787 solid Substances 0.000 claims abstract description 8
- 125000001216 2-naphthoyl group Chemical group C1=C(C=CC2=CC=CC=C12)C(=O)* 0.000 claims abstract description 4
- 230000032683 aging Effects 0.000 claims abstract description 4
- 238000001816 cooling Methods 0.000 claims abstract description 4
- 238000001035 drying Methods 0.000 claims abstract description 4
- 238000001914 filtration Methods 0.000 claims abstract description 4
- 239000000203 mixture Substances 0.000 claims abstract description 4
- 239000000843 powder Substances 0.000 claims abstract description 4
- 238000001291 vacuum drying Methods 0.000 claims abstract description 4
- 238000005406 washing Methods 0.000 claims abstract description 4
- 238000010438 heat treatment Methods 0.000 claims abstract description 3
- 239000007864 aqueous solution Substances 0.000 claims abstract 2
- 238000012544 monitoring process Methods 0.000 claims abstract 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 1
- 229910052761 rare earth metal Inorganic materials 0.000 abstract description 11
- 150000002910 rare earth metals Chemical class 0.000 abstract description 7
- -1 rare earth compound Chemical class 0.000 abstract description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 230000007547 defect Effects 0.000 description 2
- 229910052693 Europium Inorganic materials 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 description 1
- 239000007850 fluorescent dye Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/182—Metal complexes of the rare earth metals, i.e. Sc, Y or lanthanide
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a preparation method of a flexible bidentate ligand PYDE and a light conversion agent based on the flexible bidentate ligand PYDE, which comprises the following steps: in a three-necked flask, euCl was added 3 •6H 2 O, dissolving with proper amount of ethanol, adding proper amount of PYDE and 1- (2-naphthoyl) -3, 3-trifluoroacetone (NTA), and heating the mixture to 50-80deg.C in an oil bath; adjusting the pH to 6-7 by using an aqueous solution of NaOH, reacting for 1h, and monitoring the reaction end point by TLC; and finally cooling, aging, filtering, washing the solid with ethanol, and drying in a vacuum drying oven to obtain solid powder. The invention carries out coordination reaction on rare earth compound and ligand under alkaline condition; thereby improving the high temperature resistance of the rare earth light conversion agent and improving the yield thereof.
Description
Technical Field
The invention relates to the field of light conversion agents, in particular to a preparation method of a flexible bidentate ligand PYDE and a light conversion agent.
Background
Light converting agents are mainly classified into organic and inorganic types according to types, wherein the organic light converting agents are mainly organic fluorescent dyes, and most of the organic light converting agents are aromatic hydrocarbons and aromatic heterocyclic compounds. The compounds are characterized in that the molecules have large conjugated pi electron structures, n-pi and pi-pi transition energy in molecular orbits are matched with near ultraviolet and ultraviolet band energy, and the compounds have large molar absorption coefficients; after absorbing ultraviolet or near ultraviolet light, the energy is emitted in a fluorescent form, and red shift occurs, so that a light conversion effect is generated. The organic light conversion agent has the defects of easy photobleaching and short service life. The inorganic light conversion agent is a light conversion material prepared mainly by taking metal ions or rare earth elements as the center.
Most of rare earth light conversion agents on the market at present are developed by foreign companies, are high in price and are based on monopoly products. For domestic enterprises, the technical problem of neck clamping is solved. Rare earth complex compounds typically contain a rigid aromatic ring, such as phenanthroline. However, the ligand has high rigidity, and can increase quantum efficiency, but it also causes easy quenching of fluorescence of the rare earth compound, and also reduces solubility.
Disclosure of Invention
In order to overcome the defects of the prior art, the invention aims to provide a preparation method of a flexible bidentate ligand PYDE and a high-efficiency light conversion agent taking rare earth europium as a center, so that the light conversion efficiency is improved, and the production cost is reduced; solves the technical problem of neck clamping in the industry.
The technical scheme adopted by the invention is as follows:
a flexible bidentate ligand PYDE having the structural formula:
the preparation method of the flexible bidentate ligand PYDE comprises the following steps:
further, the steps are as follows: in a three-neck flask, euCl3.6H2O is added, dissolved by proper amount of ethanol, proper amount of PYDE and 1- (2-naphthoyl) -3, 3-trifluoroacetone (NTA) are added, and then the mixture is placed in an oil bath pot and heated to 50-80 ℃. The pH was adjusted to 6-7 with aqueous NaOH, reacted for 1h, and TLC monitored the end of the reaction. And finally cooling, aging, filtering, washing the solid with ethanol, and drying in a vacuum drying oven to obtain solid powder.
The beneficial effects are that: compared with the prior art, the invention has the advantages that: the flexible bidentate ligand PYDE is a novel polydentate ligand, and the yield of the rare earth light conversion agent can be improved and the cost can be reduced by carrying out coordination reaction on the rare earth compound and the ligand under alkaline conditions.
Drawings
FIG. 1 is a synthetic route diagram of the present invention.
Detailed Description
The technical scheme of the invention is described in detail below through the drawings, but the protection scope of the invention is not limited to the embodiments. The raw materials in the invention are basically general reagents.
A rare earth light conversion agent is prepared by the following steps:
in a three-necked flask, euCl was added 3 ·6H 2 O, dissolving with proper amount of ethanol, adding proper amount of PYDE and 1- (2-naphthoyl) -3, 3-trifluoroacetone (NTA), and heating the mixture to 50-80 ℃ in an oil bath pot. The pH was adjusted to 6-7 with aqueous NaOH, reacted for 1h, and TLC monitored the end of the reaction. And finally cooling, aging, filtering, washing the solid with ethanol, and drying in a vacuum drying oven to obtain solid powder.
Wherein, in order to improve the high temperature resistance of the rare earth light conversion agent, a flexible bidentate ligand PYDE is added in the preparation process, and the structural formula is as follows:
the synthetic route to PYDE is shown in FIG. 1.
As described above, although the present invention has been shown and described with reference to certain preferred embodiments, it is not to be construed as limiting the invention itself. Various changes in form and details may be made therein without departing from the spirit and scope of the invention as defined by the appended claims.
Claims (3)
1. A flexible bidentate ligand PYDE, characterized by: the structural formula is as follows:
2. the method for preparing a flexible bidentate ligand PYDE according to claim 1, wherein the synthetic route is as follows:
3. a process for preparing a light-converting agent based on the flexible bidentate ligand PYDE as claimed in claim 1, wherein EuCl is added into a three-neck flask 3 ·6H 2 O, dissolving with proper amount of ethanol, adding proper amount of PYDE and 1- (2-naphthoyl) -3, 3-trifluoroacetone (NTA), and heating the mixture to 50-80deg.C in an oil bath; adjusting the pH to 6-7 by using NaOH aqueous solution, reacting for 1h, and monitoring the reaction end point by TLC; and finally cooling, aging, filtering, washing the solid with ethanol, and drying in a vacuum drying oven to obtain solid powder.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202211710262.8A CN116621757A (en) | 2022-12-29 | 2022-12-29 | Preparation method of flexible bidentate ligand PYDE and light conversion agent |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202211710262.8A CN116621757A (en) | 2022-12-29 | 2022-12-29 | Preparation method of flexible bidentate ligand PYDE and light conversion agent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN116621757A true CN116621757A (en) | 2023-08-22 |
Family
ID=87625337
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202211710262.8A Pending CN116621757A (en) | 2022-12-29 | 2022-12-29 | Preparation method of flexible bidentate ligand PYDE and light conversion agent |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN116621757A (en) |
-
2022
- 2022-12-29 CN CN202211710262.8A patent/CN116621757A/en active Pending
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