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D-pi-A type small organic molecular dye based on di (4-styrylphenyl) aniline, synthetic method and application thereof

A technology of styrylphenyl and small molecules, which is applied in the preparation of organic dyes, organic compounds, organic chemistry, etc., can solve the problems of less than 1% total yield, high synthesis time cost and economic cost, and achieve low synthesis cost , expanding the conjugation range, and excellent photoelectric performance

Active Publication Date: 2020-05-26
NANJING UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although this kind of dye molecule exhibits relatively excellent properties, the defect that its synthesis takes more than ten steps and the total yield is often less than 1% inevitably leads to high time and economic costs for the synthesis of this kind of dye molecule.

Method used

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  • D-pi-A type small organic molecular dye based on di (4-styrylphenyl) aniline, synthetic method and application thereof
  • D-pi-A type small organic molecular dye based on di (4-styrylphenyl) aniline, synthetic method and application thereof
  • D-pi-A type small organic molecular dye based on di (4-styrylphenyl) aniline, synthetic method and application thereof

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preparation example Construction

[0033] Concrete, the synthetic method of the D-π-A type organic small molecule dye based on two (4-styrylphenyl) anilines in the present invention, its synthetic steps are as follows:

[0034] (1) Under nitrogen protection conditions, dissolve 4-bromotriphenylamine in N,,N'-dimethylformamide (DMF), and control the reaction temperature below 0°C; after a period of reaction, add to the above reaction system Phosphorus oxychloride was added to the mixture, and then the reaction temperature was controlled at 80-100°C, and the reaction time was 12-24 hours; the reaction was quenched by adding water in an ice-water bath, and after suction filtration, extraction, and solvent removal, the residue was separated and purified with a silica gel column , to obtain intermediate compound a.

[0035] (2) Under the condition of nitrogen protection, compound a and diethyl benzyl phosphate were formulated into a DMF solution, stirred for 30 minutes to dissolve it, and potassium tert-butoxide was...

Embodiment 1

[0038] Embodiment 1: the preparation of dye molecular intermediate b

[0039] The preparation method of the D-π-A type organic small molecule dye intermediate b based on two (4-styrylphenyl) anilines in the present invention, its synthetic steps are as follows:

[0040] Under nitrogen protection, add 4-bromotriphenylamine (324mg, 1.0mmol) and N,N'-dimethylformamide (DMF, 2mL) into the dry reactor, control the temperature below 0°C and stir and mix for 15min , followed by dropwise addition of phosphorus oxychloride (POCl 3 , 2.33mL, 25mmol), the mixture was stirred at 100°C for 12h. Stop the reaction and cool in an ice-water bath, slowly add water to dilute and quench, filter under reduced pressure to take the filter cake, extract with dichloromethane / water system, collect the organic phase and dry with anhydrous sodium sulfate, filter and remove the solvent under reduced pressure. The residue was separated and purified by silica gel column (eluent: petroleum ether / dichlorome...

Embodiment 2

[0042] Example 2: Synthesis and preparation of E-1 dye molecule with benzene ring as conjugated π bridge

[0043] A kind of D-π-A type organic small molecule dye precursor compound d1 and its corresponding dye E-1 based on two (4-styrylphenyl) aniline in the present invention, its molecular structure is as follows:

[0044]

[0045] The synthesis of the E-1 dye molecule and its precursor d1 in this embodiment comprises the following steps:

[0046] Under nitrogen protection conditions, compound b (350mg, 0.66mmol), 4-formylphenylboronic acid (119mg, 0.79mmol), tetrakis (triphenylphosphine) palladium (Pd (PPh 3 ) 4 , 38mg, 0.033mmol), saturated potassium carbonate solution (0.8mL) and tetrahydrofuran (5.5mL) were sequentially added into the reactor, the reaction temperature was controlled at 75°C, and the reaction was stirred and refluxed for 12h. After stopping the reaction, the reaction mixture was cooled to room temperature, filtered under reduced pressure to get the fi...

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Abstract

The invention discloses a D-pi-A type small organic molecular dye based on di (4-styrylphenyl) aniline and a synthesis method and application of the D-pi-A type small organic molecular dye. The preparation method comprises the following steps: dispersing 4-bromotriphenylamine in DMF, stirring for a period of time, adding phosphorus oxychloride, completely reacting, separating and purifying to obtain a compound a, dissolving the compound a and diethyl benzylphosphonate in DMF, adding potassium tert-butoxide, and reacting to obtain a compound b; dispersing the compound b, the compound c, tetra (triphenylphosphine) palladium and potassium carbonate into a mixed solution of dioxane and water, and separating and purifying to obtain a compound d after the reaction is completed; and carrying outa reaction between the compound d and cyanoacetic acid and ammonium acetate in acetic acid to synthesize a target molecule. An aromatic (heterocyclic) ring is introduced into the dye as a conjugate pibridge, so that the conjugate range of molecules is expanded, and intramolecular charge transfer is facilitated; the synthesized dye is simple in molecular structure, simple in synthesis steps, highin total synthesis yield and low in production cost; the dye-sensitized solar cell assembled by the dye molecules is high in photoelectric conversion efficiency and excellent in photoelectric property.

Description

technical field [0001] The invention relates to a D-π-A type organic small molecular dye based on bis(4-styrylphenyl)aniline, a synthesis method and its application in dye-sensitized solar cells. Background technique [0002] As a green renewable energy, solar energy has become one of the most promising new energy sources due to its abundant reserves, clean and pollution-free characteristics. Traditional monocrystalline silicon solar cells have high production costs due to strict requirements on purity, and polycrystalline thin-film solar cells contain toxic components that will pollute the environment. Dye-sensitized solar cells (DSSCs) have attracted extensive attention due to the advantages of a wide range of raw material sources, low cost, and strong plasticity. The properties of dye molecules directly affect their photoelectric conversion efficiency. The dyes that have been reported mainly include dye molecules containing aromatic conjugated macrocycles such as porphyr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C255/42C07D307/54C07D333/24C07C223/06C07C221/00C07C211/56C07C209/68C07C253/30C09B57/00H01G9/20
CPCC07C255/42C07D307/54C07D333/24C07C221/00C07C209/68C07C253/30C09B57/00H01G9/2059C07C223/06C07C211/56Y02E10/542Y02P70/50
Inventor 凌俐应昕彤刘逸飞许梦晨鲍本州方敬坤
Owner NANJING UNIV OF SCI & TECH
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