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Organic conjugated molecule containing branched ether chain as well as preparation and application of organic conjugated molecule

A reaction and compound technology, applied in the field of organic polymer functional materials, can solve the problems of high toxicity of processing solvents and insufficient ion transport capacity.

Active Publication Date: 2022-06-03
PEKING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] In view of the widely existing shortcomings of the processing solvents of organic conjugated molecules such as high toxicity and insufficient ion transport ability, the purpose of the present invention is to provide a novel branched ether-containing side chain and apply it to organic conjugated molecules, especially in the preparation of organic conjugated polymers

Method used

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  • Organic conjugated molecule containing branched ether chain as well as preparation and application of organic conjugated molecule
  • Organic conjugated molecule containing branched ether chain as well as preparation and application of organic conjugated molecule
  • Organic conjugated molecule containing branched ether chain as well as preparation and application of organic conjugated molecule

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Embodiment 1

[0118]

[0119] Synthesis process of compound 1: Add 5.24g of sodium hydride wrapped in 60% mineral oil to a 250mL dry double-necked bottle, replace the atmosphere of the system with nitrogen, add 120mL of dry tetrahydrofuran, and slowly dropwise add 27.4g of malonic acid Methyl ester, after the gas generation was completed, 25.0 g of benzyl bromopropyl ester was added dropwise, and the temperature was raised to 90 °C for reaction for 5 h. After the reaction, the heating was stopped, the system was cooled to room temperature, 50 mL of water was added to quench the reaction, the system was extracted with ether (50 mL×3), the organic phase was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by rotary evaporation. Distillation under reduced pressure gave 30.2 g of a colorless and transparent oily liquid with a yield of 99%. 1 H NMR (400MHz, Chloroform-d) δ7.27-7.37(m, 5H), 4.49(s, 2H), 3.73(s, 6H), 3.49(t, J=6.3Hz, 2H), 3.41(t, J=7.5Hz, 1H), 1.98...

Embodiment 2

[0121]

[0122] Synthesis route of compound 2: 0.84 g of lithium aluminum hydride was added to a 250 mL dry two-neck flask, and the system was replaced with nitrogen. Pour into dry 40 mL of tetrahydrofuran, slowly drop 2.56 g of compound 1 under an ice bath, and react at room temperature for 12 h. After the reaction was completed, 10 mL of saturated sodium sulfate solution was added dropwise in an ice bath, the system was passed through diatomaceous earth, the precipitate was washed with ethyl acetate, the mother liquor was collected, dried with anhydrous sodium sulfate, filtered, and the solvent was removed by rotary evaporation. Ester:dichloromethane=8:1 volume ratio of developing solvent column chromatography to obtain 1.69g of colorless and transparent oily product with a yield of 82%. 1 H NMR (400MHz, Chloroform-d) δ7.41-7.27(m, 5H), 4.49(s, 2H), 3.81-3.55(m, 4H), 3.47(t, J=6.4Hz, 2H), 2.80- 2.55(br,2H), 1.72(s,1H), 1.70–1.56(m,2H), 1.40–1.25(m,2H).

Embodiment 3

[0124]

[0125] Compound 3 synthesis route: add 0.45g sodium hydride wrapped in 60% mineral oil to a 250mL dry double-necked bottle, replace the system with a nitrogen atmosphere, add 30mL of tetrahydrofuran, and slowly dropwise add a tetrahydrofuran solution containing 1.06g of compound 2 , when the system no longer produces gas, drop 4.50g of MPEG3-OTs (triethylene glycol monomethyl ether p-toluenesulfonate), and react at 90°C for 12h. After the reaction was completed, heating was stopped, the system was cooled to room temperature, water was added to quench the reaction, the system was extracted with ether (50 mL×3), the organic phase was enriched, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by rotary evaporation. The residue was separated by column chromatography , the developing solvent is ethyl acetate:methanol=40:1 (volume ratio), and 0.80g of colorless and transparent oil was obtained by separation, and the yield was 33%. 1 H NMR (40...

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Abstract

The invention discloses an organic conjugated molecule containing a branched ether chain as well as preparation and application of the organic conjugated molecule. By introducing a branched ether-containing side chain to an organic conjugated molecule system, the solubility and ion affinity of the polymer are changed, the polymer can be processed by using fluoroalcohol solvents such as hexafluoroisopropanol, trifluoroethanol and the like, the toxicity of the solvents in the processing process is weakened, and electron transmission and ion transmission channels of the material are ensured at the same time. According to the organic conjugated polymer material containing the branched ether chain and an alcohol solvent processing mode, high electron mobility and volume capacitance of the material can be ensured at the same time, and the organic conjugated polymer material is applied to the field of organic electronics, including organic electrochemical transistors, organic electrochemical batteries and organic thermotropic power generation batteries, and has a wide application prospect. And excellent device sensitivity, stability and response speed can be obtained.

Description

technical field [0001] The invention relates to a class of organic conjugated molecules containing branched ether chains as side chains and a preparation method thereof, as well as the application of such organic conjugated molecules as organic semiconductor materials, belonging to the field of organic polymer functional materials. Background technique [0002] Organic conjugated molecules are a class of materials that can be processed in solution, are flexible, and can be easily modified in structure. In recent years, due to the development of synthetic methodology and the improvement of device processing technology, organic conjugated molecules have achieved a series of exciting achievements in the fields of organic solar cells (OPVs), organic light-emitting diodes (OLEDs), and organic field-effect transistors (OFETs). The remarkable achievements are gradually moving from the stage of scientific research to industrialization. [0003] The solution processability of organi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C41/22C07C43/12C07C41/26C07C43/13C07C41/16C07C43/11C07C67/343C07C69/708C07D487/04C07D209/34C07D519/00C07D409/14C07C213/02C07C217/28C07D471/06C08G61/12H01L51/05H01L51/30H01L35/24H10N10/856
CPCC07C43/11C07C69/708C07D487/04C07D209/34C07D519/00C07D409/14C07C217/28C07D471/06C07C43/126C07C43/135C08G61/126C08G61/124C08G2261/124C08G2261/1424C08G2261/3223C08G2261/3241H10N10/856H10K85/113H10K10/46Y02P20/55
Inventor 雷霆黄震李佩雲
Owner PEKING UNIV
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