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Organic dye based on tetrathienopyrrole as well as preparation method and application thereof

A technology of phenopyrrole and organic dyes, applied in the field of organic dyes and their preparation, can solve problems such as expensive preparation costs, environmental pollution restrictions, complex synthesis and separation processes, etc., and achieve improved photoelectric performance, high molar extinction coefficient, and spectral response range wide effect

Active Publication Date: 2017-02-22
SHANDONG XINGQIANG CHEM IND TECH RES INST CO LTD
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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 tetrathienopyrrole as well as preparation method and application thereof
  • Organic dye based on tetrathienopyrrole as well as preparation method and application thereof
  • Organic dye based on tetrathienopyrrole as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Preparation of organic dye 7

[0043] The synthetic route is as follows:

[0044]

[0045] 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. ACS Appl. Mater. Interfaces2014, 6, 5798−5809; 4- Hexyloxyaniline was prepared according to the literature Z.Wang, M. Liang, Y. Tan, L. Ouyang, Z. Sun, S. Xue. J. Mater. Chem. A, 2015,3, 4865–4874, raw material 5 and other reagents are available commercially.

[0046] Synthesis of Intermediate 2:

[0047]Into a 100 mL three-neck round bottom flask, add 0.604 g of raw material 1, 0.384 g of sodium tert-butoxide, 0.046 g of tris(dibenzylideneacetone) dipalladium, and 0.093 g of 1,1'-binaphthyl-2,2' -Bisdiphenylphosphine, 0.251 g 4-hexyloxyaniline and 15 mL of anhydrous toluene; under the protection of argon, the reaction system was heated to 110 °C for 8 h, and after the reaction solution was cooled to room temperature, the solvent was distilled off un...

Embodiment 2

[0056] Embodiment 2: the synthesis of organic dye 10

[0057] The synthetic route is as follows:

[0058]

[0059] The raw material 8 used in this example was prepared according to the literature Z. Wang, M. Liang, Y. Tan, L. Ouyang, Z. Sun, S. Xue. J. Mater. Chem. A, 2015, 3, 4865-4874 , Intermediate 4 was synthesized by referring to the preparation method in Example 1, and other reagents can be obtained commercially.

[0060] Synthesis of Intermediate 9:

[0061] Under the protection of argon, into a 100 mL three-neck round bottom flask, add 0.289 g raw material 5, 0.25 g intermediate 4, 0.464 g potassium carbonate, 0.019 g tetrakis(triphenylphosphine) palladium, 1.68 mL water and 10 mL Tetrahydrofuran; the reaction system was heated to 65°C for 8 h, the reaction solution was extracted with water and ethyl acetate, the organic phase was dried over anhydrous magnesium sulfate, concentrated by distillation under reduced pressure; the crude product was subjected to column ...

Embodiment 3

[0064] Embodiment 3: the synthesis of organic dye 15

[0065] The synthetic route is as follows:

[0066]

[0067] The raw material 1 used in this example can be synthesized by referring to the preparation method in Example 1, the raw material 8 can be synthesized by referring to the preparation method in Example 2, and the tripolyindene arylamine can be obtained by referring to the literature M. Liang, M. Lu, Q. Wang , W. Chen, H.Han, Z. Sun, S. Xue. Journal of Power Sources, 2011, 196, 1657–1664, and other reagents can be obtained commercially.

[0068] Synthesis of intermediate 11:

[0069] Into a 100 mL three-neck round bottom flask, add 0.604 g of raw material 1, 0.384 g of sodium tert-butoxide, 0.046 g of tris(dibenzylideneacetone) dipalladium, and 0.093 g of 1,1'-binaphthyl-2,2' - bis-diphenylphosphine, 1.12 g terdenarylamine, and 15 mL of anhydrous toluene; under the protection of argon, the reaction was heated to 110 °C for 8 h, the reaction system was cooled to ...

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Abstract

The invention discloses an organic dye based on tetrathienopyrrole as well as a preparation method and application thereof. The organic dye takes tetrathienopyrrole as a conjugated bridge. A general structural formula of the organic dye is shown in the specification, wherein in the formula, R1 is H or C1-C12 alkoxy; R2 is C1-C12 alkyl; R3 is C6-C30 aromatic rings or aromatic heterocyclic radicals. The preparation method of the dye is simple, is easy to operate and has high yield. The organic dye has a wide spectral response range in visible and near-infrared light regions and high molar extinction coefficient. Dye-sensitized solar cells prepared by using the organic dye as a single sensitizer have photoelectric conversion efficiency as high as 9.40% under the 100mW / cm<2> light condition, so the organic dye has practical significance in improving the photoelectric properties of the dye-sensitized solar cells.

Description

technical field [0001] The invention relates to the technical field of dye-sensitized solar cells, in particular to a tetrathienopyrrole-based organic dye 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.; Grätzel, 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 ca...

Claims

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Application Information

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IPC IPC(8): C09B57/00H01G9/20
CPCY02E10/542C09B57/00H01G9/2059
Inventor 王志辉陈静陈丹
Owner SHANDONG XINGQIANG CHEM IND TECH RES INST CO LTD
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