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A kind of zinc porphyrin dye sensitizer with hydrazide as anchor group and preparation method thereof

A dye sensitizer and anchoring group technology, applied in chemical instruments and methods, organic dyes, azo dyes, etc., can solve problems such as unsatisfactory stability and easy desorption, so as to improve photon capture ability and good Reference significance, the effect of high photoelectric conversion efficiency

Active Publication Date: 2019-12-10
JIANGSU UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Carboxyl is the most commonly used anchoring group, which is described in The Journal of Physical Chemistry Letters (2012), Volume 3, Page 1531-1535 and ACS Applied Materials & Interfaces (2015), Volume 7, Page 3427-3455 There is a detailed description on the page, although the carboxyl group has a good electron coupling effect between the dye and the photoanode and a high electron injection efficiency, but its stability is not ideal, and it is easy to desorb in the presence of long-term light or moisture. Therefore, it is of great scientific significance to find and develop new and efficient anchoring groups to replace carboxyl groups.

Method used

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  • A kind of zinc porphyrin dye sensitizer with hydrazide as anchor group and preparation method thereof
  • A kind of zinc porphyrin dye sensitizer with hydrazide as anchor group and preparation method thereof
  • A kind of zinc porphyrin dye sensitizer with hydrazide as anchor group and preparation method thereof

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Embodiment 1

[0043] What the present embodiment prepares is a kind of zinc porphyrin dye sensitizer with hydrazide as the anchoring group, and the reaction steps are as follows:

[0044] 1) Synthesis of compound 3:

[0045] At room temperature, compound 1 (8g, 17mmol), compound 2 (7.5g, 17mmol), anhydrous potassium carbonate (7.1g, 51mmol) were added to a three-necked flask, and then 100mL 1,4-dioxane and 20mL water, and a catalytic amount of tetrakistriphenylphosphopalladium (0.98g, 0.85mmol) was added under nitrogen protection. The reaction solution was heated to 90°C for 8 hours, then cooled to room temperature, and the solvent was removed under reduced pressure. The residue was added to water and extracted with ethyl acetate (300 mL), the organic phase was dried with anhydrous sodium sulfate, filtered and then rotary evaporated, and the residue was washed with Purified by 200-300 mesh silica gel column chromatography (petroleum ether / ethyl acetate=10 / 1) to obtain 8.6 g of compound 3 w...

Embodiment 2

[0059] 1) Synthesis of Compound 3:

[0060]At room temperature, compound 1 (7g, 14.9mmol), compound 2 (5.9g, 13.4mmol), anhydrous potassium carbonate (6.2g, 44.7mmol) were added to a three-necked flask, and then 100mL of 1,4-dioxane ring and 20 mL of water, and added a catalytic amount of tetrakistriphenylphosphopalladium (0.86 g, 0.75 mmol) under nitrogen protection. The reaction solution was heated to 90°C for 12 hours, then cooled to room temperature, the solvent was removed under reduced pressure, the residue was added with water and extracted with ethyl acetate (300 mL), the organic phase was dried with anhydrous sodium sulfate, filtered and then rotary evaporated, and the residue was used Purified by 200-300 mesh silica gel column chromatography (petroleum ether / ethyl acetate=10 / 1) to obtain 7.8 g of compound 3 with a yield of 75%. The resulting product is compared and characterized by thin-layer chromatography with the above-mentioned Example 1.

[0061] 2) Synthesis ...

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Abstract

The invention discloses a zinc porphyrin dye sensitizer with hydrazide as an anchoring group and a preparation method thereof. The dye molecule takes zinc porphyrin as the core and introduces three-dimensional spirobifluorene groups and long carbon chain modification The phenothiazine is the electron donor end, and the benzohydrazide containing the benzothiadiazole electron-withdrawing group is introduced as the electron acceptor end, thus obtaining a zinc porphyrin dye-sensitized dye containing a new type of anchoring group agent. This type of dye can be synthesized by simple suzuki coupling, desilication, sonogashira coupling, hydrazinolysis and other reactions. The prepared dye molecules show good photoelectric conversion performance when used in dye-sensitized solar cells. For new The development of the anchoring group has good reference significance and has a certain application prospect in the development and utilization of new energy.

Description

technical field [0001] The invention belongs to the technical field of new energy, and mainly relates to a zinc porphyrin dye sensitizer with hydrazide as an anchoring group and a preparation method thereof. Background technique [0002] With the world's energy crisis and environmental pollution becoming more and more serious, the development and utilization of new energy has become one of the most urgent tasks for human beings. Dye-Sensitized Solar Cells (DSSCs) have many advantages such as simple fabrication, low cost, wide source of raw materials, multi-color transparency, high photoelectric conversion efficiency, and environmental friendliness. Compared with fossil energy, it has strong competitiveness. 1991 Swiss Federal Institute of Technology The professor first reported the dye-sensitized solar cell, which achieved an energy conversion efficiency of 7.1% at a lower cost. A complete dye-sensitized solar cell device is composed of four parts: photoanode, sensitizer...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/22
CPCC07D487/22C09B47/00C09B47/045C09B47/08H01G9/2059Y02E10/542
Inventor 贾海浪黄茂战彭智杰汪冬明关明云
Owner JIANGSU UNIV OF TECH
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