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

A technology of phenanthrocarbazole and organic dyes, applied to phenanthrocarbazole donor-acceptor organic dyes and its application in dye-sensitized solar cells, can solve problems such as narrow spectral response range, and achieve low price , Reduce the charge transfer between molecules, the effect of rich sources

Active Publication Date: 2014-05-28
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

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Embodiment 1: the preparation of organic dye (Ⅰ)

[0030] The synthetic route is as follows:

[0031]

[0032] The synthesis reference of starting material 1 is Org. Lett. 2006, 8, 2221-2224.

[0033] The synthesis reference of starting material 2 is J. Mater. Chem. 2012, 22, 8394-8398.

[0034] The synthesis reference of starting material 4 is J.Org.Chem.2008, 73, 7369-7372.

[0035] Synthesis of Intermediate 3:

[0036]

[0037] In a dry Schlenk reaction flask, 2 g of compound 1 and 2.86 g of compound 2 were dissolved in 20 ml of toluene, and 60 mg of the catalyst Pd(dba) was added in the glove box 2 , 0.24 ml P(t-Bu) 3 (mass fraction 10% in hexane) and 1.49 grams of NaOt-Bu, under the protection of argon, heated to reflux to react overnight, after the reaction was complete, the temperature of the system was lowered to room temperature, extracted three times with chloroform, combined the organic phase, and the organic phase was anhydrous sulfuric acid The s...

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 3 ) 4 , heated to reflux for 2 hours, after the reaction was complete, the temperature of the system was lowered to room temperature, extracted three times with chloroform, combined the organic phases, dried the organic phases with anhydrous sodium sulfate for 2 hours, filtered out the desiccant, concentrated the filtrate, and used ethyl acetate / petroleum Ether (volume ratio 1 / 20) was used as a developer for column chromatography to obtain 2.10 g of white solid intermediate 10 with a yield of 85%.

[0083] NMR characterization data of Intermediate 10:

[0084] 1 HNMR (400MHz, CDCl 3 )δ: 7.93(d, J=7.7Hz, 2H), 7.5...

Embodiment 3

[0114] Embodiment 3: the 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 to reflux to react overnight, after the reaction was complete, the temperature of the system was lowered to room temperature, extracted three times with chloroform, combined the organic phases, dried the organic phases with anhydrous sodium sulfate for 2 hours, filtered out the desiccant, concentrated the filtrate, and used chloroform / petroleum ether (volume Ratio 1 / 1) was used as a developing solvent for column chromatography to obtain 176 mg of white solid intermediate 14 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,9H). 13 CNM...

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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 Devices made on nanocrystalline thin films 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 kind of dye-sensitized solar cell developed based on nanotechnology has attracted extensive attention and research at home and abroad because of its low cost and low energy consumption in the manufacturing process. At present, the use of po...

Claims

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Application Information

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Patent Type & Authority Applications(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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