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Organic dye based on asymmetric terthienyl pyrrole and preparation method and application thereof

A phenopyrrole and organic dye technology is applied in the field of asymmetric trithienopyrrole-based organic dyes and their preparation, which can solve the problems of expensive preparation cost, complex synthesis and separation process, environmental pollution restrictions, etc. Absorption spectrum, the effect of high electron cloud density

Active Publication Date: 2017-08-18
HUAIYIN INSTITUTE OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Among them, the complex synthesis and separation process of ruthenium-based dyes and porphyrin dyes, expensive preparation costs, and environmental pollution all limit their future industrial applications.

Method used

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  • Organic dye based on asymmetric terthienyl pyrrole and preparation method and application thereof
  • Organic dye based on asymmetric terthienyl pyrrole and preparation method and application thereof
  • Organic dye based on asymmetric terthienyl pyrrole and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Embodiment 1: the preparation of organic dye 11

[0042] The synthetic route is as follows:

[0043]

[0044] The raw material 1 used in this example was prepared according to the literature Q.Yu, W.Fu, J.Wan, X.Wu, M.Shi, H.Chen.ACSAppl.Mater.Interfaces, 2014, 6, 5798-5809; 9. 4-hexyloxyaniline and 3-bromo-2-thiophene zinc bromide According to literature Z.Wang, M.Liang, Y.Tan, L.Ouyang, Z.Sun, S.Xue.J.Mater.Chem .A, 2015, 3, 4865–4874, and other reagents can be obtained commercially.

[0045] Synthesis of Intermediate 2:

[0046] Into a 100mL single-necked round-bottom flask, add 3.75g of raw material 1 and 20mL of N-N dimethyldimethylformamide, then add 2.13g of N-bromosuccinimide to the system in batches, and keep the Light reaction for 8 hours; quenched with water, extracted with ethyl acetate, dried over anhydrous magnesium sulfate, and evaporated under reduced pressure to remove the solvent; the crude product was subjected to column chromatography (eluent: ...

Embodiment 2

[0063] Embodiment 2: the synthesis of organic dye 14

[0064] The synthetic route is as follows:

[0065]

[0066] Raw material 9 and intermediate 6 were synthesized by referring to the preparation method in Example 1, and other reagents can be purchased commercially.

[0067] Synthesis of Intermediate 12:

[0068] Under the protection of argon, in a 100mL two-necked round-bottomed flask, 0.495g of intermediate 6 and 10mL of anhydrous DMF were added successively, and then 0.187g of N-bromosuccinimide was added in batches to the reaction solution. The reaction system was React at 25°C in the dark for 8 hours; then add 0.613g of phosphorus oxychloride water to the reaction solution, and continue the reaction at 25°C for 4h; add ice water to quench the reaction, extract with ethyl acetate, dry over anhydrous magnesium sulfate, and concentrate by rotary evaporation. The product was purified by column chromatography (eluent: petroleum ether / dichloromethane = 5 / 1-1 / 1) to obtain...

Embodiment 3

[0074] Application of the dye 11 prepared in Example 1 in the preparation of dye-sensitized solar cells. Its specific use method is the same as the use method disclosed in the invention patent application with the application number 201510015966.7 and the invention title "A Carbazole-type Photosensitizing Dyestuff and Its Preparation Method and Application". Test light source: AM 1.5 (solar simulator-Oriel 91160-1000, 300W), data acquisition using Keithley 2400 digital source meter. see test results image 3 , the open circuit voltage of the battery (V oc ) is 885mV, short-circuit current density (J sc ) is 15.2mA cm -2 , the fill factor (FF) is 0.68, and the photoelectric conversion efficiency is 9.22%.

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Abstract

The invention discloses an organic dye based on asymmetric terthienyl pyrrole and a preparation method and application thereof, and belongs to the technical field of solar batteries. The organic dye is characterized in that triphenylamine is used as an electron donor, cyano-acrylate is used as an electron receptor, and an asymmetric terthienyl pyrrole unit is used as a conjugate bridge; the terthienyl pyrrole unit has a rigid co-plane structure, the electron cloud density is high, and the red shift dye absorption spectrum is effectively widened; the N-substituting group of the terthienyl pyrrole unit is easily modified, different electrons and space effect groups are conveniently introduced, the energy gap of the molecules is conveniently adjusted, the aggregation of the dye is reduced, and the photoelectric property of a battery device is improved. According to the application of the organic dye based on the asymmetric terthienyl pyrrole as the conjugate bridge in the dye-sensitized solar batteries provided by the technical scheme of the invention, after proofing by testing results, the short-circuit light current density of the battery device is 15.2mA cm<-2>, the open-circuit voltage is 885mV, and the photoelectric conversion efficiency reaches 9.22%.

Description

technical field [0001] The invention belongs to the technical field of organic dyes, in particular to an organic dye based on asymmetric trithienopyrrole and its preparation method and application. Background technique [0002] Seeking efficient and environmentally friendly renewable energy has become a common goal of all countries in the world in the 21st century. As a renewable energy source, solar energy has incomparable advantages over other energy sources. Dye-sensitized solar cells are a new type of solar cells developed based on nanotechnology by simulating photosynthesis (O’Regan, B.; M.Nature 1991,353,737.), has the characteristics of high utilization efficiency, simple process, and low cost. [0003] Dye-sensitized solar cells mainly consist of nanoporous TiO 2 Four parts: semiconductor thin film, photosensitizing dye, electrolyte and counter electrode. Among them, the photosensitizing dye plays the role of light harvesting, and its ability to capture photons ...

Claims

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Application Information

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IPC IPC(8): C09B57/00H01G9/20
CPCY02E10/542C09B57/00H01G9/2059
Inventor 王志辉苏亚高萍石慧钱国庆丁师杰陈静
Owner HUAIYIN INSTITUTE OF TECHNOLOGY
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