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Pure organic dyes based on bis(thienopyrrole) benzothiadiazole π bridges and their applications in dye-sensitized solar cells

A technology of benzothiadiazole and solar cells, which is applied in photosensitive pure organic dyes, dye-sensitized solar cells, and dye-sensitized solar cells, and can solve the problems of cumbersome synthesis steps, high price, and difficult separation and purification. , to achieve the effect of simple synthesis method, cheap raw materials and easy access to raw materials

Active Publication Date: 2020-01-10
WENZHOU MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, in the metal complex dyes, metal ruthenium is a rare and precious metal with few reserves and high price. The synthesis steps of zinc-porphyrin complex dyes are cumbersome, difficult to separate and purify, and low yields, which also limit this type of dyes. industrial development
At present, there is no bis(thienopyrrole)benzothiadiazole with electron donor-acceptor-electron donor (D-A-D) structure as the π bridge, 4-substituted phenyl as the electron donor, and benzothiadiazole as the electron donor. Oxadiazole-benzoic acid is reported as a pure organic dye with D-π-A structure as electron acceptor and anchor group

Method used

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  • Pure organic dyes based on bis(thienopyrrole) benzothiadiazole π bridges and their applications in dye-sensitized solar cells
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  • Pure organic dyes based on bis(thienopyrrole) benzothiadiazole π bridges and their applications in dye-sensitized solar cells

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] Synthesis of Pure Organic Dye H1 Based on Bis(thienopyrrole)benzothiadiazole π Bridge

[0050] (1) Synthesis of Compound 2

[0051]

[0052] Under the protection of argon, 1.25 g (3.20 mmol) of compound 1 was added to a 100 mL two-neck round bottom flask with 20 mL of o-DCB as the solvent, and the reaction system was heated to 180 ° C for 16 h. After cooling to room temperature, the reaction solvent was distilled off under reduced pressure, and the residue was separated and purified by silica gel column chromatography. Petroleum ether: ethyl acetate (2:1) was used as the mobile phase, and the obtained yellow solid product was directly put into the next reaction. Take a 100mL two-neck round bottom flask, add the yellow solid prepared above, 3.71g (19.20mmol) bromoisoctane, 2.43g (32mmol) KOH, 100mg (0.62mmol) KI and 30mL DMSO solvent. The reaction was stirred at 85° C. for 12 h under the protection of argon. After the reaction solution was cooled to room temperatur...

Embodiment 2

[0072] To the ultraviolet-visible absorption spectrum test of embodiment 1, ultraviolet-visible absorption spectrum is as figure 2 shown.

[0073] Solvent: dichloromethane

[0074] Concentration: 2×10 -5 m

[0075] Temperature: room temperature

[0076] Instrument: Shimadzu UV-2450 UV-Vis spectrophotometer

[0077] The resulting data are summarized in Table 1

[0078] The ultraviolet-visible spectral data of table 1 embodiment 1 dyestuff

[0079]

Embodiment 3

[0081] The making of dye-sensitized solar cell among the present invention is as follows:

[0082] a. Pretreatment of conductive glass (FTO): Fully clean the conductive glass in degreasing agent, absolute ethanol and deionized water with ultrasonic waves, and then dry it for later use;

[0083] b. TiO 2 Preparation of nanocrystalline particles and their slurry: at room temperature, 10mL Ti(OBu) 4 After stirring the mixture with 20mL of EtOH for 10 minutes, add 18mL of acetic acid and 50mL of deionized water to the above solution under vigorous stirring and keep stirring for 1h, then transfer the mixture into an autoclave at 230°C for 12h, and naturally cool to room temperature , filter the resulting suspension, wash with deionized water and ethanol several times respectively, and dry in an oven at 50°C for 6h to dry to obtain TiO with a particle size of about 20nm. 2 Nanocrystalline particles;

[0084] c. Take TiO 2 Add 1.0g of nanocrystalline particles to 8.0mL of ethanol...

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Abstract

The invention discloses a pure organic dye based on di(thiophenopyrrole)obenzothiadiazole Pi bridge and application of the pure organic dye to dye-sensitized solar cells and belongs to the field of application of photoelectric conversion materials in the industry of fine chemicals. A series of novel D-Pi-A structure pure organic dyes can be synthesized by taking alkoxyphenyl as an electron donor,taking di(thiophenopyrrole)obenzothiadiazole as a conjugate Pi bridge and taking benzothiadiazole-benzene-carboxyl as an electron acceptor and an anchoring group. A di(thiophenopyrrole)obenzothiadiazole unit is a large conjugate plane structure; through introduction of the di(thiophenopyrrole)obenzothiadiazole unit, the light absorption range of the dye can be effectively broadened; the molar extinction coefficient is increased; on the other hand, the unique D-A-D structure is also beneficial to Pi electron delocalization; the transfer of charge in molecules is accelerated; furthermore, the photoelectric conversion efficiency of the dye-sensitized solar cells is improved; through the combination of actions of two aspects, the pure organic dye has good application prospects in the dye-sensitized solar cells.

Description

technical field [0001] The invention relates to the technical field of photosensitive pure organic dyes and dye-sensitized solar cells, in particular to pure organic dyes based on bis(thienopyrrole) benzothiadiazole π bridges and their application in dye-sensitized solar cells. Background technique [0002] Dye-sensitized solar cells (DSSCs) are a new type of photoelectric conversion device. Compared with traditional silicon-based solar cells, dye-sensitized solar cells have the advantages of simple manufacturing process, low cost of raw materials, easy adjustment of dye structure, and large-area flexible devices. Conversion device. As an important part of DSSCs, photosensitizing dye plays a vital role in the whole battery, which plays the role of absorbing sunlight and injecting electrons. It can be said that the quality of the photosensitive dye directly determines the photoelectric conversion efficiency of the battery. Therefore, reasonable dye structure design is part...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D519/00C09B57/00H01G9/20H01G9/042
CPCC09B57/00H01G9/042H01G9/2059Y02E10/542
Inventor 黄祖胜李青云王振操全云云
Owner WENZHOU MEDICAL UNIV
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