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Method for synthesizing polystyrene high molecular ligand taking 8-hydroxyquinoline as ligand group

A hydroxyquinoline-based, polystyrene technology, applied in the field of synthesis of organic macromolecular ligands, can solve problems such as easy crystallization and difficult film formation, and achieve the effect of broad application prospects

Inactive Publication Date: 2014-08-20
HARBIN ENG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The purpose of the present invention is to provide a method that not only retains the coordination function of 8-hydroxyquinoline and metal ions, but also solves the difficulties in film formation and easy crystallization of small molecule materials and metal ions to form small molecule metal complexes. Synthesis method of polystyrene macromolecular ligand with 8-hydroxyquinolinyl as coordinating group

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025](1) Synthetic method of 5-bromo-8-tert-butoxycarbonyloxyquinoline: take 3.94g (17.59mmol) of 5-bromo-8-hydroxyquinoline, follow the method of 5-bromo-8-hydroxyquinoline, two Di-tert-butyl carbonate, 4-dimethylaminopyridine molar ratio is that the ratio of 1:1.2:0.05 takes di-tert-butyl carbonate and 4-dimethylaminopyridine, 5-bromo-8-hydroxyquinoline, di Di-tert-butyl carbonate and 4-dimethylaminopyridine were added to 500ml of n-hexane, the reaction temperature was controlled at 25°C, and the reaction time was 6h. The reaction solution was filtered, and the filtrate was recrystallized in n-hexane after removing the solvent by rotary evaporation.

[0026] (2) The synthesis method of 5-trimethylsilylethynyl-8-tert-butoxycarbonyloxyquinoline: under the protection of anhydrous and oxygen-free nitrogen, add 5-bromo-8-tert-butoxycarbonyl to the reaction flask Oxyquinoline 4.428g (13.67mmol), add reaction solvent 55ml (triethylamine / tetrahydrofuran, 4.5 / 1, V / V), according to 5...

Embodiment 2

[0031] (1) The synthetic method of 5-bromo-8-tert-butoxycarbonyloxyquinoline is the same as Example 1.

[0032] (2) The synthesis method of 5-trimethylsilylethynyl-8-tert-butoxycarbonyloxyquinoline is the same as Example 1.

[0033] (3) The synthetic method of 5-ethynyl-8-tert-butoxycarbonyloxyquinoline is the same as Example 1.

[0034] (4) The click reaction of 5-ethynyl-8-tert-butoxycarbonyloxyquinoline and azidopolystyrene to synthesize polystyrene with 8-tert-butoxycarbonyloxyquinolyl end group: in the absence of Under the protection of water and oxygen-free nitrogen, add 2.9g of azidopolystyrene (number-average molecular weight: 2310, PDI=1.12) and 11ml of N,N-dimethylformamide into the reaction bottle, according to the method of azidopolystyrene , 5-ethynyl-8-tert-butoxycarbonyloxyquinoline, cuprous bromide, PMDETA molar ratio 1:1.5:1:1 is added to 5-ethynyl-8-tert-butoxycarbonyloxyquinoline , cuprous bromide and PMDETA. The reaction temperature was controlled at 50°...

Embodiment 3

[0037] (1) The synthetic method of 5-bromo-8-tert-butoxycarbonyloxyquinoline is the same as Example 1.

[0038] (2) The synthesis method of 5-trimethylsilylethynyl-8-tert-butoxycarbonyloxyquinoline is the same as Example 1.

[0039] (3) The synthetic method of 5-ethynyl-8-tert-butoxycarbonyloxyquinoline is the same as Example 1.

[0040] (4) The click reaction of 5-ethynyl-8-tert-butoxycarbonyloxyquinoline and azidopolystyrene to synthesize polystyrene with 8-tert-butoxycarbonyloxyquinolyl end group: in the absence of Under the protection of water and oxygen-free nitrogen, add 3.4g of azidopolystyrene (number-average molecular weight: 4930, PDI=1.10) and 12ml of N,N-dimethylformamide into the reaction bottle, according to the method of azidopolystyrene , 5-ethynyl-8-tert-butoxycarbonyloxyquinoline, cuprous bromide, PMDETA molar ratio 1:1.2:1:1 is added to 5-ethynyl-8-tert-butoxycarbonyloxyquinoline , cuprous bromide and PMDETA. The reaction temperature was controlled at 70°...

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Abstract

The invention provides a method for synthesizing a polystyrene high molecular ligand taking 8-hydroxyquinoline as a ligand group. The method comprises the following steps of: (1) synthesizing 5-bromo-8-tert-butoxycarbonyloxyquinoline; (2) synthesizing 5-trimethylsilylacetylene-8-tert-butoxycarbonyloxyquinoline; (3) removing a trimethyl silicane group of 5-trimethylsilylacetylene-8-tert-butoxycarbonyloxyquinoline, and synthesizing 5-acetylenyl-8-tert-butoxycarbonyloxyquinoline; (4) reacting the 5-acetylenyl-8-tert-butoxycarbonyloxyquinoline with click of azido-polystyrene to synthesize polystyrene of which a terminal group is 8-tert-butoxycarbonyloxyquinoline; and (5) synthesizing a polystyrene high molecular ligand taking 8-hydroxyquinoline as a ligand group. The ligand prepared with the method takes 8-hydroxyquinoline as a ligand group, has the potential of forming a metal complex together with metal ions such as zinc, magnesium, aluminum and the like, and has wide application prospects in the fields of biology, electrofluorescence, magnetic functional high molecules, electrochemical catalysis, polymer photovoltaic devices and the like.

Description

technical field [0001] The invention relates to a method for synthesizing organic macromolecule compounds, in particular to a method for synthesizing organic macromolecule ligands. Background technique [0002] 8-Hydroxyquinoline is one of the earliest luminescent materials researched in the field of organic electroluminescence with high brightness, high luminous efficiency and low driving voltage [Tang C W, Vanslyke S A. Appl Phys Lett, 1987, 51:913-915]. However, 8-hydroxyquinoline metal complexes are difficult to form a film, the device preparation process is complicated, and recrystallization is prone to occur during the film formation and working process, resulting in a decrease in device stability. In response to the above problems, more and more researchers are focusing on the polymerization of such materials to maintain the excellent luminescent properties of 8-hydroxyquinoline metal complexes and improve their processing properties. After 8-hydroxyquinoline is poly...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08F112/08C08F8/30C08F8/00
Inventor 张春红张爽王海伦苏广东耿倩倩
Owner HARBIN ENG UNIV
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