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Quinacridone derivatives and uses thereof

A technology for quinacridone and derivatives, which is applied in the field of quinacridone derivatives, and can solve problems such as expensive preparation process and restrictions on widespread use

Inactive Publication Date: 2011-12-14
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although dye sensitizers containing precious metals have high energy conversion efficiency (about 11.5%), their widespread use is restricted due to expensive raw materials and complicated preparation processes.

Method used

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  • Quinacridone derivatives and uses thereof
  • Quinacridone derivatives and uses thereof
  • Quinacridone derivatives and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1 and Embodiment 2

[0045]

[0046] With the teaching of the above preparation methods, those skilled in the art can prepare other compounds contained in formula I without creative effort.

[0047] Application of quinacridone derivatives provided by the invention in the preparation of photosensitizers for dye-sensitized solar cells:

[0048]The preparation of the battery is firstly to pretreat the conductive glass, and then apply the titanium dioxide slurry on the treated conductive glass, after high temperature treatment, immerse in the dye bath and absorb for 12 hours to form the working electrode of the battery. A dye-sensitized solar cell was prepared by encapsulating the configured electrolyte between the working electrode and the platinum-coated counter electrode with a sealant. The test of battery performance is to lead wires from the working electrode and counter electrode of the battery respectively, and connect them to the battery performance testing device. The working area of ​​the...

Embodiment 1

[0053]

[0054] Add 4.68g quinacridone (15mmol) and 2.88g NaH (120mmol) into a 250mL three-neck flask, inject 100mLTHF under the protection of argon, and heat to reflux for 1 hour. Then inject 11.58g bromooctane (60mmol), reflux reaction for 24 hours. After the reaction was completed, the reaction solution was poured into water to precipitate a solid, which was filtered with suction, and the crude product was purified on a silica gel column (petroleum ether:dichloromethane=1:1) to obtain an orange solid i with a yield of 62%.

[0055] 1 H NMR (CDCl 3 , 400MHz), δ: 0.90(t, 6H), 1.30(m, 12H), 1.47(m, 4H), 1.61(m, 4H), 2.03(m, 4H), 4.51(t, 4H), 7.28( m, 2H), 7.51(m, 2H), 7.75(m, 2H), 8.58(dd, J 1 =1.9Hz,J 2 =2.2Hz, 2H), 8.77(d, J=3.7Hz, 2H).

[0056]

[0057] Add 1.08g compound i (2mmol), 356mgNBS (2mmol) and 50mLCCl in 100mL one-necked flask 4 , reflux reaction for 12 hours under the protection of argon. After the reaction was complete, the solvent was removed and a...

Embodiment 3

[0079]

[0080] Add 258mg XII-1 (0.3mmol) to a 250mL three-necked flask, a small amount of Pd(PPh 3 ) 4 , 12.5mL 2mol.L -1 K 2 CO 3 Solution and 25mL tetrahydrofuran, under the protection of argon, heated to reflux for half an hour, then poured into 25mL tetrahydrofuran solution containing furan boronic acid aldehyde (84mg, 0.6mmol), and reacted under reflux for 12 hours. After the reaction was completed, the liquid was separated and the water layer was removed, spin-dried, then extracted with water and dichloromethane, the oil phase was taken out, the solvent was removed and then applied to a silica gel column (developing solvent was dichloromethane) to obtain 250 mg of a red solid (compound XIII-2) , yield 95.4%.

[0081] 1 H NMR (CDCl 3 , 400MHz), δ: 0.90(m, J=6.7Hz, 6H), 1.36(m, 12H), 1.50(m, 4H), 1.64(m, 4H), 2.01(m, 4H), 4.51(m, 4H), 6.88(d, J=3.7Hz, 1H), 7.06(t, J=7.3Hz, 2H), 7.17(m, 6H), 7.29(m, 4H), 7.34(d, J=3.7Hz, 1H), 7.52(m, 4H), 7.88(d, J=9.1Hz, 1H), 8...

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Abstract

The invention relates to a quinacridone derivative and application thereof. The quinacridone derivative is obtained by subjecting quinacridone (matrix) to chemical modification (connection with electron-donating groups and electron-withdrawing groups of triphenylamine). In the quinacridone derivative which contains donor-acceptor electronic groups and is designed and prepared in the invention, electrons are easier to transfer in an excitation state, so that the quinacridone derivative achieves the performance of effectively converting optical energy into electric energy and can be used as a photosensitizer for a dye-sensitized nanocrystal solar cell. Experiments show that the quinacridone derivative provided by the invention has favorable photosensitization property.

Description

technical field [0001] The present invention relates to a quinacridone derivative and its use. Background technique [0002] Solar energy is an inexhaustible and inexhaustible clean energy, and converting it into electrical energy is a good way to utilize it. Dye-sensitized solar cells have the advantages of low cost, simple manufacturing process, and good stability. They have attracted widespread attention from many people and have great potential practical value. [0003] A dye-sensitized solar cell (DSSC) is mainly composed of a substrate coated with a transparent conductive film, a porous nanocrystalline titanium dioxide film, a dye photosensitizer, a redox electrolyte solution, and a transparent counter electrode. The broad-spectrum absorption, high-efficiency, and low-cost dye photosensitizer is the most important part of dye-sensitized solar cells. Although noble metal-containing dye sensitizers have high energy conversion efficiency (about 11.5%), their widespread ...

Claims

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Application Information

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IPC IPC(8): C07D471/04C09B48/00H01L51/46H01G9/004H01G9/20H01M14/00
CPCY02E10/542Y02E10/549Y02E10/50
Inventor 花建丽杨家保武文俊郭福领李晶田禾
Owner EAST CHINA UNIV OF SCI & TECH
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