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Asymmetrical dye molecule adopting tetraphenylporphin as core, and preparation method thereof

A tetraphenylporphyrin and asymmetric technology, which is applied in the field of preparation of porphyrin dye molecules, can solve the problems that the photoelectric conversion efficiency of porphyrin-based batteries is not as good as that, affects the performance of photovoltaic cells, and the molecules are easy to aggregate, etc. Electron and electron-withdrawing ability, conversion efficiency improvement, and low price effect

Inactive Publication Date: 2012-04-11
UNIV OF SCI & TECH BEIJING
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] At present, in DSSCs with liquid electrolytes, porphyrin-based dyes are easy to aggregate molecules due to their weak absorption in the long-wave band and the excellent planarity of molecules, which affects the performance of photovoltaic cells, making the photoelectric conversion efficiency of porphyrin-based cells lower than that polypyridine ruthenium

Method used

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  • Asymmetrical dye molecule adopting tetraphenylporphin as core, and preparation method thereof
  • Asymmetrical dye molecule adopting tetraphenylporphin as core, and preparation method thereof
  • Asymmetrical dye molecule adopting tetraphenylporphin as core, and preparation method thereof

Examples

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Effect test

Embodiment 1

[0024] What this example prepared was the dye molecule described in the general formula, wherein X=4, M=2H, and the reaction formula is as follows:

[0025]

[0026] Firstly, p-bromobenzaldehyde (14.8g, 80mmol) was dissolved in 200ml of propionic acid, the solution was heated to reflux at 140°C, pyrrole (5.36g, 80mmol) was added dropwise, stirred for 30min, cooled to room temperature, and half of the solvent was evaporated , and add 100ml methanol, the mixture is placed in the refrigerator overnight, after filtration, use petroleum ether / dichloromethane=2 / 3 column chromatography, pass through CHCI 3 Recrystallized with methanol=1:5 to obtain purple solid compound 4-4-bromobenzoporphyrin (4.2 g, 22.6%).

[0027] 4-4-Bromobenzoporphyrin (931mg, 1mmol), bistetraalkylamine (1.86g, 4mmol), K 2 CO 3 (828mg, 6mmol) and copper powder (320mg, 5mmol) were added in anhydrous DMF (100mL), then it was 2 Heated to reflux for 24h under protection, removed DMF, and used CHCI for solid ...

Embodiment 2

[0033] What this example prepared was the dye molecule described in the general formula, wherein X=8, M=2H, and the reaction formula is as follows:

[0034]

[0035]Firstly, p-bromobenzaldehyde (14.8g, 80mmol) was dissolved in 200ml of propionic acid, the solution was heated to reflux at 140°C, pyrrole (5.36g, 80mmol) was added dropwise, stirred for 30min, cooled to room temperature, and half of the solvent was evaporated , and add 100ml methanol, the mixture is placed in the refrigerator overnight, after filtration, use petroleum ether / dichloromethane=2 / 3 column chromatography, pass through CHCI 3 Recrystallized with methanol=1:5 to obtain purple solid compound 4-4-bromobenzoporphyrin (4.6 g, 22.9%).

[0036] 4-4-Bromobenzoporphyrin (931mg, 1mmol), bis-octaylamine (1.86g, 3mmol), K 2 CO 3 (828mg, 6mmol) and copper powder (320mg, 5mmol) were added in anhydrous DMF (100mL), then it was 2 Heated to reflux for 24h under protection, removed DMF, and used CHCI for solid 3 Ex...

Embodiment 3

[0039] What this example prepared was the dye molecule described in the general formula, wherein X=4, M=Zn, and the reaction formula is as follows:

[0040]

[0041] Firstly, p-bromobenzaldehyde (14.8g, 80mmol) was dissolved in 200ml of propionic acid, the solution was heated to reflux at 140°C, pyrrole (5.36g, 80mmol) was added dropwise, stirred for 30min, cooled to room temperature, and half of the solvent was evaporated , and add 100ml methanol, the mixture is placed in the refrigerator overnight, after filtration, use petroleum ether / dichloromethane=2 / 3 column chromatography, pass through CHCI 3 Recrystallized with methanol=1:5 to obtain purple solid compound 4-4-bromobenzoporphyrin (3.9 g, 21.6%).

[0042] 4-4-Bromobenzoporphyrin (931mg, 1mmol), bistetraalkylamine (1.86g, 4mmol), K 2 CO 3 (828mg, 6mmol) and copper powder (320mg, 5mmol) were added in anhydrous DMF (100mL), then it was 2 Heated to reflux for 24h under protection, removed DMF, and used CHCI for solid ...

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Abstract

The present invention relates to a class of asymmetrical dye molecules adopting tetraphenylporphin as the core, and a preparation method thereof. According to the structure of the dye molecule, donors with different carbon chain lengths and an acceptor with a triple bond are asymmetrically substituted on the periphery of the structure, and a proper core metal ion is selected to enhance the electron absorption ability and the electron donating ability. The preparation method comprises an Adler synthesis method for synthesis of 4-4-bromophenyl porphyrin and subsequent substitution reactions of the donor and the acceptor. The prepared dye molecules can be applicable for the DSCC, can provide good photoelectric conversion properties, and have great application prospects in energy development and utilization. The materials of the present invention have the liquid crystal properties under a certain conditions, such that the materials can form the discotic liquid crystals, and have great application potential in the application fields of photoelectric devices.

Description

technical field [0001] The invention belongs to the technical field of dye molecules and their preparation, and in particular relates to a preparation method of porphyrin dye molecules. Background technique [0002] Porphyrin has a large polarizable π-electron system, and push-pull electron groups can be introduced around it, and can form complexes with transition metals, so the properties of porphyrin derivatives can be adjusted through molecular design. By introducing conjugated groups with different electron-donating and accepting abilities, the molecular conjugated system and the degree of delocalization of electrons in the molecule can be expanded, so that the energy level difference between the HOMO and LUMO of the porphyrin molecule can be freely adjusted, thereby changing the entire The electrochemical and optical properties of molecules can be used as nonlinear optical materials, photoelectric conversion materials, molecular electronic devices, etc. [0003] In ter...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B47/00
Inventor 杨洲杜政才王冬金召奎梁蓬霞弥永胜
Owner UNIV OF SCI & TECH BEIJING
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