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Phenanthro-carbazole donor-acceptor organic dye and application thereof in dye-sensitized solar cell

A technology of phenanthrene carbazoles and organic dyes, applied in the field of phenanthrene carbazoles donor and acceptor organic dyes and its application in dye-sensitized solar cells, which can solve the problems of narrow spectral response range and achieve low price , reduce intermolecular charge transfer, reduce the effect of difficulty

Active Publication Date: 2015-07-22
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The purpose of the present invention is to solve the defect of narrow spectral response range of existing organic dyes, and to provide a kind of phenanthrocarbazole donor-acceptor organic dyes and its application in dye-sensitized solar cells

Method used

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  • Phenanthro-carbazole donor-acceptor organic dye and application thereof in dye-sensitized solar cell

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Example 1: Preparation of organic dye (I)

[0030] The synthetic route is as follows:

[0031]

[0032] Synthesis of starting material 1 is referenced in Org. Lett. 2006, 8, 2221-2224.

[0033] Synthesis of starting material 2 is referenced in J. Mater. Chem. 2012, 22, 8394-8398.

[0034] Synthesis of starting material 4 is referenced in J. Org. Chem. 2008, 73, 7369-7372.

[0035] Synthesis of Intermediate 3:

[0036]

[0037] In a dry Schlenk reaction flask, dissolve 2 g of compound 1 and 2.86 g of compound 2 in 20 ml of toluene, add 60 mg of catalyst Pd(dba) in the glove box 2 , 0.24 ml P(t-Bu) 3 (10% mass fraction in hexane) and 1.49 g NaOt-Bu, heated and refluxed overnight under argon protection, after the reaction was completed, the temperature of the system was lowered to room temperature, extracted with chloroform three times, the organic phases were combined, and the organic phase was treated with anhydrous sulfuric acid. After drying over sodium for ...

Embodiment 2

[0077] Embodiment 2: the preparation of organic dye (II)

[0078]

[0079] Synthesis reference of starting material 9 Bioorg. Med. Chem. Lett, 2012, 22, 415-420.

[0080] Synthesis of Intermediate 10:

[0081]

[0082]In a dry Schlenk reaction flask, 2.13 g of compound 9 and 2.9 ml of hexamethylditin were dissolved in 20 ml of toluene, and 809 mg of Pd (PPh) were added under argon atmosphere. 3 ) 4 , heated and refluxed for 2 hours, after the reaction was completed, the temperature of the system was lowered to room temperature, extracted with chloroform three times, the organic phases were combined, the organic phases were dried with anhydrous sodium sulfate for 2 hours, the desiccant was filtered out, the filtrate was concentrated, and the ethyl acetate / petroleum Ether (volume ratio 1 / 20) was used as a developing solvent for column chromatography to obtain 2.10 g of intermediate 10 as a white solid with a yield of 85%.

[0083] NMR characterization data of intermedia...

Embodiment 3

[0114] Example 3: Preparation of organic dye (III)

[0115]

[0116] Synthesis of Intermediate 14:

[0117]

[0118] In a dry Schlenk reaction flask, 200 mg of intermediate 10 and 861 mg of 4,7-dibromobenzothiadiazole were dissolved in 20 ml of toluene, and 49 mg of Pd (PPh 3 ) 2 Cl 2 , heated and refluxed overnight, after the reaction was completed, the temperature of the system was lowered to room temperature, extracted with chloroform three times, the organic phases were combined, the organic phases were dried with anhydrous sodium sulfate for 2 hours, filtered to remove the desiccant, and the filtrate was concentrated and washed with chloroform / petroleum ether (volume ratio 1 / 1) as a developing solvent column chromatography to obtain 176 mg of intermediate 14 as a white solid with a yield of 76%. NMR characterization data of intermediate 14:

[0119] 1 HNMR (400MHz, CDCl 3 )δ:8.08(d,J=8.4Hz,2H),7.88(d,J=8.4Hz,2H),7.83(d,J=7.6Hz,1H),7.52(d,J=7.6Hz,1H) , 1.60 (s...

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Abstract

The invention provides a phenanthro-carbazole donor-acceptor organic dye and application thereof in a dye-sensitized solar cell, and belongs to the field of organic dyes. The organic dye utilizes the characteristics of phenanthro-carbazole structural units such as a large plane conjugated system and higher fluorescence quantum yield to be connected with the structural units with different electronic withdrawing abilities so as to realize step-by-step regulation and control to the dye molecular energy level; meanwhile, a molecular non-conjugated skeleton is connected with a long alkyl chain, so that the solubility of phenanthro-carbazole units is improved, the difficulty in molecular synthesis and device processing is reduced, and charge transfer among molecules caused by molecular aggregation is reduced; meanwhile, raw materials of phenanthro-carbazole compounds are abundant in source, low in price and easy to cut structurally.

Description

technical field [0001] The invention belongs to the technical field of organic dyes, and in particular relates to a phenanthrocarbazole donor-acceptor organic dye and its application in dye-sensitized solar cells. Background technique [0002] 1991, Switzerland The research group used the trinuclear ruthenium dye RuL reported by Amadelli et al. 2 (μ-(CN)Ru(CN)L′ 2 ) 2 (L=2,2′-bipyridine-4,4′-dicarboxylic acid, L′=2,2′-bipyridine) as a sensitizer adsorbed on high-quality TiO 2 The device fabricated on the nanocrystalline thin film achieved a photoelectric conversion efficiency of 7.1% under simulated sunlight, which was a milestone in the development of dye-sensitized solar cells, which set off a research boom in dye-sensitized solar cells. This dye-sensitized solar cell developed based on nanotechnology has received extensive attention and research at home and abroad due to its low cost and low energy consumption during manufacturing. At present, the use of polypyridin...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09B57/00H01G9/20H01G9/042
CPCY02E10/542
Inventor 王鹏姚朝阳蔡艳春许名飞张敏
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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