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A kind of silicon-containing condensed pentacyclic bridged organic dye and its preparation method and application

A technology of organic dyes and reactions, applied in organic dyes, silicon organic compounds, organic chemistry, etc., to achieve high optical coefficient, inhibit interface electron recombination, and prevent self-aggregation of dyes

Active Publication Date: 2022-05-27
HUAIYIN INSTITUTE OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Silicon-containing fused rings have achieved excellent photoelectric properties in the field of DSSCs due to their unique electronic and spatial configurations. However, current research is mainly focused on dithienosilole units, and new types of silicon-containing fused rings with more fused rings are There are few reports in the literature, therefore, the development of new silicon-containing fused ring bridged organic dyes has important theoretical and practical value

Method used

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  • A kind of silicon-containing condensed pentacyclic bridged organic dye and its preparation method and application
  • A kind of silicon-containing condensed pentacyclic bridged organic dye and its preparation method and application
  • A kind of silicon-containing condensed pentacyclic bridged organic dye and its preparation method and application

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Experimental program
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Effect test

Embodiment 1

[0034] This embodiment provides a silicon-containing fused pentacyclic organic dye, the chemical formula of which is shown in formula (VIII)

[0035]

[0036] The preparation method of above-mentioned organic dye (formula (VIII) compound) is as follows:

[0037] The compound of formula (1) used in this example is based on literature Wang Z, Miu L, Yao H, et al.Organicsensitizers featuring 9H-thieno[2′,3′:4,5]thieno[3,2-b]thieno[ 2',3':4,5]thieno[2,3-d]pyrrole core for high performance dye-sensitized solarcells.Dyes Pigments 2019;162:126-35. Prepared; the compound of formula (6) is obtained according to document O. Bettucci, T. Skaltsas, M. Calamante, et al. ACS Appl. Energy Mater. 2019, 2, 5600-561. Prepared; other reagents can be obtained commercially.

[0038] S1: react the compound of formula (I) with the compound of formula (II) to generate the compound of formula (III);

[0039]

[0040] This step is specifically: under argon protection, under the condition of low...

Embodiment 2

[0060] This embodiment is roughly the same as Embodiment 1, and the main differences are:

[0061] Synthesis of compound of formula (III):

[0062] Under argon protection and low temperature -78°C, 1.47g of the compound of formula (I) dissolved in 30mL of anhydrous tetrahydrofuran was added to a 100mL eggplant-shaped reaction flask. After 5 minutes of low temperature reaction, 2.34mL of n-butyllithium was slowly added. (2.4mol / L), 794mg of compound (II) was added after warm reaction for 1h, the refrigeration was turned off, and slowly returned to room temperature; the reaction was performed for 12h. Water and ethyl acetate were added for extraction, the organic phase was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain 782 mg of compound (III) as a yellow-green viscous liquid with a yield of 46%.

[0063] Synthesis of compound of formula (IV):

[0064] Add 600 mg of compound (III) to a 100 mL single-neck flask, dissol...

Embodiment 3

[0073] This embodiment is roughly the same as Embodiment 1, and the main differences are:

[0074] Synthesis of compound of formula (III):

[0075] Under argon protection, under the condition of low temperature -78 ℃, into a 100 mL eggplant-shaped reaction flask, add 981 mg of the compound of formula (I) dissolved in 30 mL of anhydrous tetrahydrofuran, and after 5 minutes of low temperature reaction, slowly add n-butyllithium 1.56 mL ( 2.4mol / L), after warm reaction for 1h, add 794mg of compound of formula (II), turn off refrigeration, slowly return to room temperature; react for 8h. Water and ethyl acetate were added for extraction, the organic phase was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain 737 mg of the compound of formula (III). It was a yellow-green viscous liquid with a yield of 65%.

[0076] Synthesis of compound of formula (IV):

[0077] Add 600 mg of compound (III) to a 100 mL single-neck flask, d...

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Abstract

The invention relates to the technical field of organic dyes, and discloses a silicon-containing condensed pentacyclic-bridged organic dye and its preparation method and application. The chemical structural formula of the organic dye is as follows: Rigid three-dimensional three-dimensional configuration, stronger ability to inhibit the aggregation of dye molecules and slow down the electron recombination at the battery interface, and has higher photothermal stability; in addition, the organic dye has a simple preparation method, high yield, and low preparation cost. A kind of photoelectric material with excellent performance, when it is used as a single sensitizer in dye-sensitized solar cells, it can obtain a photoelectric conversion efficiency of more than 7.2%, and its device can still maintain more than 93% photoelectricity after 480 hours of continuous operation. Transformation efficiency, showing great application prospects.

Description

technical field [0001] The invention relates to the technical field of organic dye-sensitized solar cells, in particular to a silicon-containing fused pentacyclic bridged organic dye and a preparation method and application thereof. Background technique [0002] With the increasingly serious pollution problems brought about by the use of coal resources, the utilization of solar energy as an important clean energy has attracted more and more attention at home and abroad. Among them, dye-sensitized solar cells (DSSCs) are a new type of photovoltaic technology developed based on nanotechnology that simulates photosynthesis (O’Regan, B.; M.Nature 1991, 353, 737.), has the advantages of high efficiency, simple manufacturing process and low cost. Dye sensitizers are the core components of DSSCs and play a decisive role in the photovoltaic performance of the cells. Organic dyes have attracted more and more attention from scientists due to their wide source of raw materials, flex...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F7/08C09B23/04H01G9/20
CPCC07F7/0816C07F7/083C09B23/04C09B23/0058C09B23/0091H01G9/2059Y02E10/542Y02P70/50
Inventor 蔡鹏陈瑾任炎炎张淦郑菲
Owner HUAIYIN INSTITUTE OF TECHNOLOGY
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