Organic monomer containing 8-hydroxyquinoline boron, conjugated polymer based on monomer, preparation method and application

A technology of hydroxyquinoline boron and conjugated polymers, which is applied in the fields of compounds containing elements of Group 3/13 of the periodic table, organic chemistry, chemical instruments and methods, etc., and can solve problems such as limiting the wide application of materials

Active Publication Date: 2017-01-11
SHAANXI NORMAL UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Obviously, the development of new synthesis methods for organic conjugated small molecules and polymers containing main group elements, and the preparation of a series of organic co

Method used

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  • Organic monomer containing 8-hydroxyquinoline boron, conjugated polymer based on monomer, preparation method and application
  • Organic monomer containing 8-hydroxyquinoline boron, conjugated polymer based on monomer, preparation method and application
  • Organic monomer containing 8-hydroxyquinoline boron, conjugated polymer based on monomer, preparation method and application

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preparation example Construction

[0104] 2. Preparation of fluorescent film

[0105] The resulting compound was dissolved in chloroform to prepare a 1-10 mg / mL stock solution. Each time, 20-50 μL of the stock solution was dropped and coated on the surface of a specially treated glass substrate to prepare a fluorescent film.

[0106] Preferably, in the step of preparing monomer and polymer in the present invention:

[0107] In the step 1) of synthesizing compound 1, the optimal molar ratio of the described diisopropylamine, borane dimethyl sulfide, n-butyllithium, trimethylchlorosilane and tetrahydrofuran is: 1:1:1:1: 4.4;

[0108] In step 2) of synthesizing compound 2, the optimal molar ratio of compound 1, 1-(4-alkyl)bromobenzene, magnesium, hydrochloric acid and tetrahydrofuran is: 1:3:3.3:15:98.5;

[0109] In the step 3) of synthesizing compound 3, the optimal molar ratio of compound 2, 5,7-diiodo-8-hydroxyquinoline and ether is 1:1:57.8;

[0110] In the step 4) of the synthetic compound 4, the alkyl su...

Embodiment 1

[0119] Preparation of an organic monomer and four conjugated polymers

[0120] ①Synthesis of compound 1

[0121] Under an argon protective atmosphere, 7 mL of diisopropylamine was added to 18 mL of anhydrous tetrahydrofuran solution and fully stirred, and under ice bath conditions, 5 mL of borane dimethyl sulfide in tetrahydrofuran (10 mol / L) was added dropwise In the above reaction solution, after the dropwise addition, the reaction was continued for 1.5 hours under ice-bath conditions; Stir for 2 hours; finally, add 6.4 mL of trimethylchlorosilane dropwise to the reaction system, and immediately produce a large amount of white precipitates, and stir at room temperature for 2 hours after all the addition. After the reaction, the reaction solution was left to stand for 1 hour and filtered under the protection of argon to obtain a colorless and transparent filtrate which was compound 1, which was stored under the protection of argon for future use, with a yield of about 99%. ...

Embodiment 2

[0143] In this example, in step ① of the synthesis of compound 1, 7 mL of diisopropylamine was added to 32.5 mL of anhydrous tetrahydrofuran solution under an argon protective atmosphere and fully stirred, and 5 mL of diisopropylamine was added dropwise under ice bath conditions The tetrahydrofuran solution (10mol / L) of borane dimethyl sulfide was added to the above reaction solution. After the dropwise addition, the reaction was continued for 1.5 hours under ice bath conditions; then 20 mL of n-butyl lithium was added dropwise to the reaction system n-Hexane solution (2.5mol / L), continue to stir for 2 hours under ice-bath conditions; finally, add 6.4mL trimethylchlorosilane dropwise to the reaction system, a large amount of white precipitate will be produced immediately, after all the addition, stir at room temperature 2 hours. The molar ratio of diisopropylamine, borane dimethyl sulfide, n-butyllithium, trimethylchlorosilane and tetrahydrofuran is 1:1:1:1:5.5. After the rea...

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Abstract

The invention discloses an organic monomer containing 8-hydroxyquinoline boron, a conjugated polymer based on the monomer, a preparation method and application, and belongs to the technical field of preparation of the conjugated polymer containing a main group element and application of photoelectrical properties of the conjugated polymer. The preparation method of the compound has the outstanding advantages of being easy and convenient to operate, mild in reaction condition, capable of conducting large-scale production, high in adaptability to substrate, free of column chromatography purification and the like; the prepared monomer and the polymer are good in photochemical stability, high in fluorescence quantum yield and excellent in solubility, and a firm foundation is laid for sensing application and photoelectric property application of the monomer and the polymer.

Description

technical field [0001] The invention belongs to the technical field of preparation of conjugated polymers containing main group elements and their application in photoelectric properties, and specifically relates to a class of organic monomers containing 8-hydroxyquinoline boron and conjugated polymers based on the monomers as well as preparation methods and application. Background technique [0002] As an emerging research field, organic optoelectronics is a new interdisciplinary subject that spans chemistry, materials, physics, and information. It has received extensive attention from academia and industry in recent years. At present, the rapid development of organic optoelectronic devices such as organic electroluminescent diodes, organic field effect transistors, organic photovoltaic cells, organic sensors, and organic information storage has demonstrated the incomparable advantages of inorganic semiconductor devices. As the most important component of organic optoelect...

Claims

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Application Information

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IPC IPC(8): C08G61/12C08J5/18G01N21/64G01N21/33C07F5/02
CPCC07F5/02C08G61/122C08G61/126C08G2261/124C08G2261/3223C08G2261/3328C08G2261/411C08G2261/414C08G2261/5222C08J5/18C08J2365/00G01N21/33G01N21/643G01N2021/6432
Inventor 房喻何刚祁彦宇黄杰张维东
Owner SHAANXI NORMAL UNIV
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