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Preparation and application of a class of trifluoromethyl-modified platinum complexes

A platinum complex, trifluoromethyl technology, applied in the field of phosphorescent materials, to achieve the effect of excellent aggregation-induced luminescence properties

Active Publication Date: 2021-10-15
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, the effect of trifluoromethyl on the aggregation-induced luminescent properties of metal complexes has not been reported in the literature

Method used

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  • Preparation and application of a class of trifluoromethyl-modified platinum complexes
  • Preparation and application of a class of trifluoromethyl-modified platinum complexes
  • Preparation and application of a class of trifluoromethyl-modified platinum complexes

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] The synthesis of embodiment 1 complex Pt1

[0033] (1) Synthesis of cyclometal ligands:

[0034] In the air, add 1.0mmol of 2-bromo-4-trifluoromethylpyridine, phenylboronic acid (1.5equiv.), potassium carbonate (2.0equiv.), palladium acetate (1.5%equiv.) , and then add 8 mL of ethanol-water mixed solution with a volume ratio of 3:1, and carry out Suzuki cross-coupling reaction under magnetic stirring at 80 ° C. Track the reaction process by thin-layer chromatography. After the reaction is complete, add 20 mL of saturated saline, Extract with dichloromethane, combine the organic phases, concentrate under reduced pressure, and separate by column chromatography to obtain the ring metal ligand.

[0035] (2) Synthesis of neutral platinum complexes:

[0036] Add cyclometal ligands, 1.2 equivalents of potassium tetrachloroplatinate, and 8 mL of ethylene glycol monoethyl ether / water (3:1, v / v) mixed solution into a 25 mL round-bottomed two-neck flask, under nitrogen protectio...

Embodiment 2

[0037]The synthesis of embodiment 2 complex Pt2

[0038] The preparation method of Example 2 is the same as that of Example 1, except that the 2-bromopyridine derivative used in the synthesis of the ring metal ligand in Example 2 is 2-bromo-5-trifluoromethylpyridine.

[0039] The yield of Pt2 is 64%, and the structural characterization data are as follows: 1 H NMR (400MHz, CDCl 3 )δ9.30(s,1H),7.99(d,J=8.2Hz,1H),7.68(d,J=8.4Hz,1H),7.63(d,J=7.6Hz,1H),7.47(d, J=7.6Hz,1H),7.24(s,1H),7.12(t,J=7.4Hz,1H),5.49(s,1H),2.03(d,J=2.4Hz,6H).HRMS(EI, m / z) theoretical value: 517.0697[M+H] + , measured value: 517.0703[M+H] + .

Embodiment 3

[0040] The synthesis of embodiment 3 complex Pt3

[0041] (1) Synthesis of cyclometal ligands:

[0042] In air, add 1.0 mmol of 2-bromopyridine, 3-trifluoromethylphenylboronic acid (1.5 equiv.), potassium carbonate (2.0 equiv.), and palladium acetate (1.5% equiv.) to a round-bottomed two-necked flask successively, Then add 8 mL of ethanol-water mixed solution with a volume ratio of 3:1, and carry out Suzuki cross-coupling reaction with magnetic stirring at 80 ° C. Track the reaction process by thin-layer chromatography. After the reaction is complete, add 20 mL of saturated saline, and use Extract with dichloromethane, combine the organic phases, concentrate under reduced pressure, and separate by column chromatography to obtain the ring metal ligand.

[0043] (2) Synthesis of platinum complexes:

[0044] Add cyclometallic ligands, 1.2 equivalents of potassium tetrachloroplatinate and 8 mL of ethylene glycol monoethyl ether / water (3:1, v / v) mixed solution into a 25 mL round-...

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Abstract

A preparation method and application of a trifluoromethyl-modified platinum complex belongs to the field of phosphorescent materials. The present invention uses trifluoromethyl-substituted 2-phenylpyridine derivatives as ring metal ligands and acetylacetone or 1,10-phenanthroline as auxiliary ligands to synthesize eight platinum complexes. The platinum complexes prepared by the invention all have aggregation-induced luminescent properties, and have important application value in the field of phosphorescent materials.

Description

technical field [0001] The invention relates to a preparation method and application of a trifluoromethyl-modified platinum complex, which belongs to the field of phosphorescent materials. Background technique [0002] Traditional fluorescent molecules usually have strong fluorescence in dilute solutions, and the fluorescence is weakened or even quenched at high concentrations. In 2001, Tang Benzhong et al. found that a small organic molecule had no fluorescence in dilute solution, but showed bright fluorescence emission in the aggregated state (Chem. Commun., 2001, 18, 1740-1741). They described this new The phenomenon is called aggregation-induced emission (Aggregation-Induced Emission, abbreviated as AIE). [0003] The strong electron-withdrawing group trifluoromethyl group can increase the oxidation potential of the luminescent material and enhance the oxidation resistance. The introduction of trifluoromethyl into the molecular structure of metal complexes can effectiv...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F15/00C09K11/06
CPCC07F15/0086C09K11/06C09K2211/1029C09K2211/1044C09K2211/185
Inventor 刘春陶玮彤
Owner DALIAN UNIV OF TECH
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