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Pyrene D-pi-A type asymmetric disc dye compound

A dye compound, asymmetric technology, applied in the preparation of organic compounds, azo dyes, organic dyes, etc., can solve problems such as reduced efficiency, and achieve the effects of low cost, simple synthesis process and easy preparation

Active Publication Date: 2013-04-17
UNIV OF SCI & TECH BEIJING
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The coupling reaction is used to introduce the donor and acceptor groups on the pyrene ring, the product has good solubility, is easy to synthesize and separate, has low cost and has good photoelectric conversion efficiency; through the control of the position of the donating and withdrawing electron groups, Overcomes efficiency loss caused by aggregation of dye molecules

Method used

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  • Pyrene D-pi-A type asymmetric disc dye compound
  • Pyrene D-pi-A type asymmetric disc dye compound
  • Pyrene D-pi-A type asymmetric disc dye compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] to:R 1 structured as R 2 structured as The synthetic method of this compound is introduced as an example

[0032] Bromination reaction of A pyrene: Dissolve 10mmol pyrene (2.02g) in 50mL nitrobenzene, put it in a 100mL single-necked bottle, gradually add 30mmol liquid bromine (2.00mL) dropwise at room temperature, after the dropwise addition, raise the temperature to To 100-120 degrees, stop the reaction after 16-24 hours of reaction. Pour the product into a solution containing 200mL of 10% sodium bisulfite and stir to remove the remaining bromine, change the water every ten minutes until the solution is colorless; separate the liquid to remove the water layer, add methanol to the organic layer to produce particles After filtration, washed with water and ethanol, dried to obtain 2.81 g of a yellow powder product, the yield was 78%.

[0033] B Sonogashira coupling reaction: Dissolve 5mmol of the product (1.80g) obtained in A in a mixed solution of 30mL tetrahydrof...

Embodiment 2

[0039] with R 1 structured as R 2 structured as The synthetic method of this compound is introduced as an example

[0040]Bromination reaction of A pyrene: Dissolve 10mmol pyrene (2.02g) in 50mL nitrobenzene, put it in a 100mL single-necked bottle, gradually add 30mmol liquid bromine (2.00mL) dropwise at room temperature, after the dropwise addition, raise the temperature to To 100-120 degrees, stop the reaction after 16-24 hours of reaction. Pour the product into a solution containing 200mL of 10% sodium bisulfite and stir to remove the remaining bromine, change the water every ten minutes until the solution is colorless; separate the liquid to remove the water layer, add methanol to the organic layer to produce particles After filtration, washed with water and ethanol, dried to obtain 2.81 g of a yellow powder product, the yield was 78%.

[0041] B Sonogashira coupling reaction: Dissolve 5mmol of the product (1.80g) obtained in A in a mixed solution of 30mL tetrahydro...

Embodiment 3

[0047] with R 1 structured as R 2 structured as The synthetic method of this compound is introduced as an example

[0048] Bromination reaction of A pyrene: Dissolve 10mmol pyrene (2.02g) in 50mL nitrobenzene, put it in a 100mL single-necked bottle, gradually add 30mmol liquid bromine (2.00mL) dropwise at room temperature, after the dropwise addition, raise the temperature to To 100-120 degrees, stop the reaction after 16-24 hours of reaction. Pour the product into a solution containing 200mL of 10% sodium bisulfite and stir to remove the remaining bromine, change the water every ten minutes until the solution is colorless; separate the liquid to remove the water layer, add methanol to the organic layer to produce particles After filtration, washed with water and ethanol, dried to obtain 2.81 g of a yellow powder product, the yield was 78%.

[0049] B Sonogashira coupling reaction: Dissolve 5mmol of the product (1.80g) obtained in A in a mixed solution of 30mL tetrahydr...

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Abstract

The invention relates to a pyrene D-pi-A type asymmetric disc dye compound, and a preparation method of a pyrene derivative material. A length-controllable flexible chain of the asymmetric pyrene derivative material serves as a donator (alkyl or alkoxy phenylacetylene and bis-alkylaniline), and a carboxy side chain serves as a receptor (benzoic acid or iso-cyanoacrylate). The prominent advantages of the pyrene disc compound applied to a dye-sensitized solar cell are simple synthesis and separation, low cost, better photoelectric conversion efficiency, and the like. In addition, electron-withdrawing and electron-donating groups are added through a coupled reaction to form the asymmetric D-pi-A type disc dye compound, and the problem of efficiency reduction caused by dye molecular aggregation is solved by controlling positions of the electron-withdrawing and electron-donating groups. The compound has very high ultraviolet absorption and photoelectric conversion efficiency, and has a wide application prospect in organic-dye-sensitized solar cells.

Description

technical field [0001] The invention belongs to the field of organic photoelectric materials, and relates to a kind of pyrene D-π-A type asymmetric discoid dye compound with certain photoelectric conversion efficiency. Background technique [0002] Since the beginning of the 20th century, with the rapid development of human industrial civilization, mineral resources such as coal, oil, and natural gas have been increasingly depleted, and the resulting energy crisis and environmental pollution have become serious problems that need to be solved urgently. Solar energy has many advantages, such as inexhaustible, inexhaustible, safe and reliable, non-polluting, not restricted by geographical environment, etc., and has been paid more and more attention. Organic solar cells have shown their great development potential due to their outstanding advantages such as wide source of materials, low production cost, low energy consumption, flexibility, and easy mass production, and have bec...

Claims

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Application Information

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IPC IPC(8): C07C65/28C07C51/367C07C229/52C07C227/10C07C255/41C07C253/30C09B57/00
Inventor 王冬梁蓬霞杨洲弥永胜赵玉真
Owner UNIV OF SCI & TECH BEIJING
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