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A large-volume electron-rich phosphine ligand catalyst and its preparation method and application

A catalyst and system technology, applied in the field of large-volume electron-rich phosphine ligand catalyst and its preparation, can solve the problems of not obtaining high-yield and high-molecular-weight polymers and the like

Inactive Publication Date: 2011-12-07
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, high yield and high molecular weight polymers have not been obtained when catalysts with such ligands are applied to the synthesis of thiophenes and polythiophenes.

Method used

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  • A large-volume electron-rich phosphine ligand catalyst and its preparation method and application
  • A large-volume electron-rich phosphine ligand catalyst and its preparation method and application
  • A large-volume electron-rich phosphine ligand catalyst and its preparation method and application

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Embodiment 1

[0035] R in embodiment 1, preparation formula I is CH 3 Compound L1

[0036]

[0037] Compound 1 Compound 2 Compound L1

[0038] 1) Synthesis of compound 1: put 15mmol 1,3-dimethoxybenzene into the reaction flask, add 60ml of dry tetrahydrofuran (THF), and slowly drop into 15mmol n-BuLi (n-butyl base lithium) and then the reaction mixture was raised to room temperature to continue the reaction for 5-10 h, and then the reaction mixture was cooled to -78 ° C, and 14 mmol o-bromochlorobenzene was slowly added dropwise to obtain a light yellow crude product, which was recrystallized from methanol to obtain a white solid. Yield 84%.

[0039] 2) Synthesis of compound 2: Add 1 mmol of compound 1 to the reaction flask, add 100 ml of tetrahydrofuran, under nitrogen atmosphere, control the temperature at -78 ° C, slowly drop 1.2 mmol of n-BuLi, and continue stirring at this temperature for 20 min. The reaction mixture was cooled to -95°C, and 0.95 mmol P(OPh) was added by syringe ...

Embodiment 2

[0041] Embodiment 2, monomer G4 and M2 are in catalyst Pd2 (dba) 3 Polymerization under / L1 catalysis

[0042]

[0043] (Compound G4) (Compound M2)

[0044] PD 2 (dba) 3 Purchased from Shanghai Darui Fine Chemicals Co., Ltd., CAS code 51364-51-3 (52409-22-0).

[0045] Compound G4 was prepared with reference to the literature method, and the specific preparation method was as follows: (1) under nitrogen atmosphere, 1mol 1,4-dibromo-2-(bromomethyl)-5-toluene and 1mol phlorotriphenol were mixed, acetone was used as solvent, Then add 5mol of salt of wormwood, heat and reflux reaction, generate compound 5-(2,5-dibromo-4-methyl benzyloxy)-1,3-benzenediol;

[0046] (2) Under a nitrogen atmosphere, 1mol compound 5-(2,5-dibromo-4-methylbenzyloxy)-1,3-benzenediol is mixed with 2mol dimethyl (1,1-dimethylbenyloxy) Base) chlorosilane reacts to generate compound 3;

[0047] (3) Under nitrogen atmosphere, mix 1mol of 5-(bromomethyl)-1,3-benzenediol with 2mol of bromine, acetone as ...

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Abstract

The invention discloses a bulky electron-rich phosphine ligand compound and a preparation method thereof. The structural formula of the phosphine ligand is shown in formula I; wherein, R represents an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group or an aryl group substituted by an alkane. The method for preparing the compound of formula I comprises the following steps: reacting the compound shown in formula II with the compound shown in formula III at -90°C to -60°C for 2-5h, and then reacting at room temperature for 5-15 hours, namely have to. The lone electron pair on the methoxyl oxygen in the large-volume thiophene-containing ligand synthesized by the present invention can increase the electron cloud density of the molecule, which is beneficial to stabilizing the Pd intermediate in the reaction process, preventing cyclization, and increasing steric hindrance. Improve catalyst life. In addition, the thiophene ring is a group with a stronger electron supply than aryl or alkyl, which is beneficial to increase the electron cloud density on the phosphine and improve the activity of the ligand. The ligand of the present invention is coordinated with the palladium catalyst and then applied to Suzuki coupling or polymerization reaction to synthesize photoelectric polymer materials with high molecular weight and high yield.

Description

technical field [0001] The invention relates to a large-volume electron-rich phosphine ligand catalyst as well as its preparation method and application. Background technique [0002] As the world is facing an energy crisis, photoelectric conversion technology is considered to be one of the most important renewable energy sources. Among them, polymer solar cells have received extensive attention due to their advantages of low cost, light weight, and large-area preparation. One of the important factors to obtain high photoelectric conversion efficiency is to develop electron donor materials with excellent properties. Researching and preparing high-efficiency catalysts is an effective means of synthesizing donor materials. At present, the highest conversion efficiency has reached 8%. [0003] π-conjugated polymers have broad application prospects in the fields of organic / polymer light-emitting diodes, organic / polymer solar cells, organic field-effect transistors, and biosen...

Claims

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Application Information

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IPC IPC(8): C07F9/6553B01J31/22C08G61/12
Inventor 刘美芳薄志山李翠红
Owner INST OF CHEM CHINESE ACAD OF SCI
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