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Carbazole dye sensitizer and preparation method and application thereof

A dye sensitizer and dye sensitization technology are applied in the field of dye sensitized solar cells, which can solve the problems of inability to meet the diverse needs of dye sensitizers and have few types, and achieve the effect of excellent photoelectric conversion performance.

Active Publication Date: 2018-05-11
浙江工业大学上虞研究院有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are very few types of such dye sensitizers at present, which cannot meet the diverse needs of dye sensitizers for dye-sensitized solar cells.

Method used

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  • Carbazole dye sensitizer and preparation method and application thereof
  • Carbazole dye sensitizer and preparation method and application thereof
  • Carbazole dye sensitizer and preparation method and application thereof

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Experimental program
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preparation example Construction

[0029] The present invention provides the preparation method of carbazole dye sensitizer described in above-mentioned technical scheme, comprises the following steps:

[0030] Mixing a compound having a structure shown in formula II, cyanoacetic acid, piperidine and a polar organic solvent, and performing a condensation reaction under a protective atmosphere to obtain a carbazole dye sensitizer having a structure shown in formula I;

[0031]

[0032] R in formula II includes or C 4 h 9 -.

[0033] In the present invention, the compound having the structure shown in formula II is specifically a compound having the structure shown in formula IIa or formula IIb:

[0034]

[0035] In the present invention, there is no special limitation on the source of the compound having the structure shown in formula II, and it can be prepared by using commercially available products or preparation methods well known to those skilled in the art. In an embodiment of the present invent...

Embodiment 1

[0070] To prepare a carbazole dye sensitizer with a structure shown in formula Ia, the preparation steps are as follows:

[0071]

[0072] (1) N-phenylcarbazole borate (IVa, 12mmol, 3.78g), 6-bromo-3-(thiophen-2-yl)-2H-coumarin (V, 13.2mmol, 4.05g) , Pd(PPh 3 ) 4 (1.20mmol, 1.39g) and potassium carbonate aqueous solution (24mL, 2mol / L) were mixed with tetrahydrofuran (59mL), and Suzuki reaction was carried out at 65°C for 12h; the obtained Suzuki reaction material was mixed with water, and extracted three times with dichloromethane , combined organic layers, anhydrous Na 2 SO 4 Drying, separation by column chromatography (the volume ratio of petroleum ether and dichloromethane in the eluent is 3:1), and the obtained eluate was dried to obtain 2.87 g of a light yellow solid with a yield of 51%.

[0073] After testing, the melting point of the light yellow solid is 261-263°C.

[0074] The obtained light yellow solid is carried out nuclear magnetic resonance detection, an...

Embodiment 2

[0085] Prepare the carbazole dye sensitizer with the structure shown in formula Ib, the preparation step flow process is as follows:

[0086]

[0087] (1) Add N-butylcarbazole borate (IVb, 18.8mmol, 5.55g), 6-bromo-3-(thiophen-2-yl)-2H-coumarin (V, 11.26mmol, 3.46g ), Pd(PPh 3 ) 4 (1.88mmol, 2.17g) and potassium carbonate aqueous solution (37.6mL, 2mol / L) were mixed with tetrahydrofuran (87mL), and Suzuki reaction was carried out at 66°C for 12h; the obtained Suzuki reaction material was mixed with water, extracted with dichloromethane for 3 times, combined organic layers, anhydrous Na 2 SO 4 Drying, separation by column chromatography (the volume ratio of petroleum ether and dichloromethane in the eluent is 3:1), and the obtained eluent was dried to obtain 3.71 g of light yellow solid with a yield of 44%.

[0088] After detection, the melting point of the light yellow solid is 188-189°C.

[0089] The obtained light yellow solid is carried out nuclear magnetic resonanc...

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Abstract

The invention provides a carbazole dye sensitizer of a structure as shown in the formula I. The carbazole dye sensitizer takes carbazole as an auxiliary electron donor, takes coumarin as an electron donor, takes thiophene as a bridge bond and takes cyanoacetic acid as an electron acceptor, a D-D-pi-A type dye sensitizer is formed, and a new available compound is provided for diversification of thedye sensitizer. The experimental results show that the carbazole dye sensitizer has the excellent photoelectric conversion function, and the photoelectric conversion efficiency can reach 2.48%. The invention further provides a preparation method of the dye sensitizer. The preparation method is simple, easy to implement and suitable for industrial production.

Description

technical field [0001] The invention relates to the technical field of dye-sensitized solar cells, in particular to a carbazole dye sensitizer and its preparation method and application. Background technique [0002] As the most promising alternative to conventional inorganic solar cells, dye-sensitized solar cells (DSSCs) have attracted considerable attention in the past decade due to their high performance and low-cost fabrication. Photosensitizers play the most important role in the performance of dye-sensitized solar cells. For example, some divalent ruthenium complex dyes exhibit excellent photovoltaic performance and high photoelectric conversion efficiency. Compared with noble metal ruthenium complex dyes, metal-free organic dyes are promising in dye-sensitized solar cell research due to their high molar absorptivity and low production cost. In order to design and synthesize organic dyes with new structures, chemists have made great efforts. Thousands of non-metalli...

Claims

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Application Information

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IPC IPC(8): C09B57/00H01G9/20H01G9/042
CPCC09B57/00H01G9/2059Y02E10/542Y02P70/50
Inventor 韩亮陈雅倩郝学良叶青李郁锦高建荣
Owner 浙江工业大学上虞研究院有限公司