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Indole [3,2-b] pyrrole dye, and preparation method and applications thereof

A 2-b, indole technology, applied in the direction of organic dyes, methenyl/polymethenyl dyes, chemical instruments and methods, etc., can solve the difficulty of separation and purification of ruthenium polypyridine complexes, restrictions on large-scale practical use, high cost, etc. problem, to achieve the effect of simple structure, easy synthesis and strong absorption

Active Publication Date: 2015-11-11
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, ruthenium is a rare and precious metal, and the separation and purification of ruthenium polypyridine complexes is also quite difficult. The high cost of DSSCs limits its large-scale practical application.
However, there are no reports of indolo[3,2-b]pyrrole dyes

Method used

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  • Indole [3,2-b] pyrrole dye, and preparation method and applications thereof
  • Indole [3,2-b] pyrrole dye, and preparation method and applications thereof
  • Indole [3,2-b] pyrrole dye, and preparation method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Synthesis of Indolo[3,2-b]pyrrole Dye TX-2

[0032] The following reactions were all carried out in a dry environment under the protection of argon.

[0033] (1) Synthesis of compound 2

[0034]

[0035]1.41 g (5 mmol) of compound 1 was dissolved in 50 mL of dry o-dichlorobenzene, then 3.94 g (15 mmol) of triphenylphosphine was added and vigorously stirred to reflux. After the reaction was complete, the solvent was removed under reduced pressure. Poured into water, added dichloromethane (3 x 30ml) for extraction. The organic layer was washed with water, dried and concentrated. The crude product was crudely purified through a 10 cm high silica gel pad to obtain 0.63 g of a khaki solid with a yield of 50%. 1 HNMR (CDCl 3 ,400MHz,ppm):δ7.48-7.53(m,3H),7.18-7.21(m,1H),6.74(d,J=2.8Hz,1H),6.03(d,J=2.8Hz,1H), 3.96(s,3H). 13 CNMR (CDCl 3 ,100MHz,ppm): δ141.4,132.4,126.0,122.3,121.7,116.8,115.3,114.4,113.7,90.42,35.4.

[0036] (2) Synthesis of compound 3

[0037] ...

Embodiment 2

[0058] The dyes TX-1 and TX-2 prepared in Example 1 were tested by ultraviolet-visible absorption spectrum. Its UV-Vis absorption spectrum is as follows figure 1 shown.

[0059] Solvent: dichloromethane

[0060] Concentration: 2×10 -5 m

[0061] Temperature: room temperature

[0062] Instrument: ShimadzuUV-2450 UV-Vis spectrophotometer

[0063] From figure 1 It can be seen that the dyes TX-1 and TX-2 prepared in Example 1 have strong absorption of sunlight in the visible range, and their maximum absorption wavelengths are 479nm and 476nm respectively.

Embodiment 3

[0065] Fabricate a dye-sensitized solar cell device with the dye of Example 1: the fired nano-titanium dioxide electrode is immersed in a solution containing 3×10 -4 mol / L dye TX-1 or TX-2 in tetrahydrofuran solution for 12 hours; then take it out, rinse with absolute ethanol, and blow dry. The dye-sensitized solar cell is composed of the sensitized electrode, the platinum-plated glass electrode and the electrolyte. at 100mW / cm 2 The open circuit voltage of the dye TX-1 measured under the light intensity is 0.69V, and the short circuit current density is 9.54mA / cm 2 , the fill factor is 0.77, and the photoelectric conversion efficiency is 5.04%. Under the same conditions, the open circuit voltage of dye TX-2 is 0.54V, and the short circuit current density is only 3.21mA / cm 2 , the fill factor is 0.66, and the photoelectric conversion efficiency is only 1.16%. Their photocurrent and photovoltage curves are shown in figure 2 .

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Abstract

The invention discloses an indole [3,2-b] pyrrole dye, and a preparation method and applications thereof, and belongs to the field of photoelectric conversion material in fine chemical engineering. According to the indole [3,2-b] pyrrole dye, indole [3,2-b] pyrrole is taken as a core framework, and cyanoacetic acid is taken as a receptor group. The structure of indole [3,2-b] pyrrole contains two nitrogen atoms, electron cloud density is high, electron donating ability is high, relatively strong absorption can be observed in visible region, and the indole [3,2-b] pyrrole dye can be applied to dye-sensitized solar cells as a photosensitizer.

Description

technical field [0001] The invention relates to the field of photoelectric conversion materials in fine chemical industry, in particular to a class of indole[3,2-b]pyrrole dyes and its preparation method and application. technical background [0002] Dye-sensitized solar cells (DSSCs) are a novel device for converting solar energy into electricity. Compared with traditional silicon-based solar cells, this type of cell has the advantages of simple structure and low manufacturing cost, and is a type of photoelectric conversion device with broad application prospects. The structural design of dyes is crucial for the photoelectric conversion efficiency of such cells. Currently, ruthenium polypyridine complexes have the highest photoelectric conversion efficiency. However, ruthenium is a rare and precious metal, and the separation and purification of ruthenium polypyridine complexes is also quite difficult. The high cost of DSSCs limits their large-scale practical application. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B23/04C07D487/04H01G9/20
CPCY02E10/542
Inventor 曹德榕戴学新
Owner SOUTH CHINA UNIV OF TECH