Nitrogen-containing bidentate heterocyclic substituted tetrazole rare earth complex and preparation method thereof

A technology for rare earth complexes and azole compounds is applied in the field of synthesis of tetrazole ligands and rare earth complexes, and achieves the effects of high yield, simple operation and short reaction time.

Active Publication Date: 2016-04-27
GUANGDONG SYNYOO NEW MATERIAL
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] Up to now, no new rare earth luminescent complexes suitable for practical applications, even for OLED display and lighting technology have been reported.

Method used

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  • Nitrogen-containing bidentate heterocyclic substituted tetrazole rare earth complex and preparation method thereof
  • Nitrogen-containing bidentate heterocyclic substituted tetrazole rare earth complex and preparation method thereof
  • Nitrogen-containing bidentate heterocyclic substituted tetrazole rare earth complex and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Example 1: Synthesis and fluorescence emission spectrum of tris[5-(2,2'-bipyridin-6-yl)-1,2,3,4-1H-tetrazole]europium(III) (compound 5) test

[0040] Step 1: Preparation of N-oxy-2,2’-bipyridine (compound 2)

[0041]

[0042] First, compound (1) 2,2’-bipyridine (100g) and acetic acid (500mL) were added into a 2L three-neck flask, stirred evenly, and 30% H 2 o 2 (70mL), heated to 70-75°C, stirred for 3 hours, cooled to room temperature, added 30% H 2 o 2 (70mL), continue heating to 60-80°C, and react for 3 hours. After cooling to room temperature, acetic acid was concentrated under reduced pressure to obtain a reddish-brown viscous oil, which was diluted with water (1000 mL), and the pH was adjusted to 8-9 with solid sodium carbonate. The resulting solution was extracted with dichloromethane (1000 mL+500 mL×3), and the organic phases were combined and dried with anhydrous sulfuric acid. After filtration, the filtrate was concentrated under pressure to obtain a r...

Embodiment 2

[0055] Example 2: Synthesis and fluorescence emission spectrum of tris[5-(2,2'-bipyridin-6-yl)-1,2,3,4-1H-tetrazole]terbium(III) (compound 6) test

[0056]

[0057] Compound 4 (7.4 g) and terbium trichloride hexahydrate (3.7 g) obtained in the previous example were dissolved in 50 mL of a mixed solvent of absolute ethanol and water at a volume ratio of 1:3 to form solutions C and D. Add 1.2g of sodium hydroxide to solution C, and stir for half an hour. Then, the D solution was added dropwise into the reaction bottle of the C solution, and the reaction was stirred at room temperature for 8 hours. After the reaction, the solvent was evaporated to dryness under reduced pressure, and the solid was vacuum-dried at 50° C. for 3 hours to obtain 9.3 g of yellow powder.

[0058] MS: [M+1] 828.9, TbC 33 h 21 N 18 M.W.=828, the ratio of M+H peak 829 and 830 peak height is detected close to the isotopic abundance ratio of Tb 2:1.

[0059] It can be known from the fluorescence emi...

Embodiment 3

[0060] Example 3: Preparation and fluorescence emission spectrum of tris[5-(2,2'-bipyridin-6-yl)-1,2,3,4-1H-tetrazole]thulium(III) (compound 7) test

[0061]

[0062] Compound 4 (6.7g) obtained in Example 1 and thulium nitrate (3.5g) were respectively dissolved in 50mL of a mixed solvent of 1,2-propanediol and water with a volume ratio of 1:3 to form solutions E and F. Add 1.2g of sodium hydroxide into solution E, and stir for half an hour. Then, the F solution was added dropwise into the reaction bottle of the E solution, and stirred and reacted for 48 hours under the condition of 60° C. water bath. After the reaction, the solvent was evaporated to dryness under reduced pressure, and the solid was dried in vacuum at 50° C. for 4 hours to obtain 9.1 g of yellow powder.

[0063] MS: [M+1] 838.7, TmC 33 h 21 N 18 M.W.=838, the height ratio of M+H peaks 839 and 841 was detected in accordance with the isotopic abundance ratio of Tm. Mass spectrum such as figure 1 shown. ...

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Abstract

The invention provides a nitrogen-containing double-tooth heterocyclic ring substituted tetrazole type rare-earth complex LnL3 expressed by the formula I, wherein Ar is a nitrogen-containing double-tooth heterocyclic ring; the center rare-earth ion Ln is any one of yttrium, lanthanum, cerium, praseodymium, neodymium, samarium, europium, gadolinium, terbium, dysprosium, holmium, erbium, thulium, ytterbium and lutetium. The preparation method of the nitrogen-containing double-tooth heterocyclic ring substituted tetrazole type rare-earth complex LnL3 is characterized in that a nitrogen-containing double-tooth heterocyclic ring substituted tetrazole type three-tooth compound, namely a dipyridyl tetrazole type three-tooth compound or phenanthroline tetrazole type three-tooth compound, is taken as a single ligand, and simultaneously, coordination saturation is satisfied, and the tetrazole group in the complex serves as negative irons to realize electrically neutral charge balance together with center rare-earth metal cations. The obtained rare-earth complex is high in thermal stability, can be prepared into a device through an evaporation film-forming process or a solution film-forming process. Besides, the preparation method has the advantages of high yield, of the product has high purity, reaction time is short and operation is simple; and as a result, the cost is greatly reduced.

Description

Technical field: [0001] The invention relates to a synthesis method of a novel nitrogen-containing bidentate heterocyclic substituted tetrazole ligand and a rare earth complex thereof. Background technique: [0002] my country has a unique resource advantage for the development of rare earth applications. Among the world's rare earth resources that have been identified, 80% (36-37%, WIKI) of rare earth resources are in my country, and the variety is complete. In order to protect resources and avoid environmental problems caused by over-exploitation, my country began to control the export of rare earth ores in 2009, but was protested by countries such as the United States, Japan and Europe. This reflects the preciousness of rare earth resources and the necessity and urgency of vigorously developing rare earth deep processing from another angle. In view of my country's rich and distinctive rare earth resources, when my country's rare earth industry urgently needs to transform...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F5/00C09K11/06
Inventor 史华红宋继国方航兵梁东宁尚恩
Owner GUANGDONG SYNYOO NEW MATERIAL
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