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Tetrazole porphyrin metal complexes, synthesis thereof and applications of the metal complexes as dye sensitizing agents

A technology of tetrazolium porphyrin and metal complexes, which can be used in organic chemistry, photosensitive equipment, electrolytic capacitors, etc., can solve the problems of ruthenium complex consumption, pollution, production restrictions, etc., and achieves the promotion of photoelectric conversion efficiency, and the raw materials are simple and easy. The effect of obtaining, good photoelectric performance

Inactive Publication Date: 2016-03-16
NORTHWEST NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, solar cells on the market mainly use silicon semiconductor materials, but due to its high cost and serious pollution, it is necessary to develop new energy sources
Dye-sensitized solar cells have been a research hotspot in recent years. The highest photoelectric conversion efficiency of dye-sensitized solar cells dominated by polypyridine ruthenium complexes has exceeded 11%, but ruthenium complexes consume a lot of energy and bring great harm to the environment. Large-scale pollution, so large-scale production is actually subject to great restrictions

Method used

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  • Tetrazole porphyrin metal complexes, synthesis thereof and applications of the metal complexes as dye sensitizing agents
  • Tetrazole porphyrin metal complexes, synthesis thereof and applications of the metal complexes as dye sensitizing agents
  • Tetrazole porphyrin metal complexes, synthesis thereof and applications of the metal complexes as dye sensitizing agents

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] 1. Synthesis of phenyl zinc porphyrin——5,10,15,20-tetrakis(3-tetrazolyl)phenyl zinc porphyrin

[0039] (1) Add freshly distilled pyrrole (7.5mmol, 0.52mL) and 3-cyanobenzaldehyde (7.5mmol, 0.98g) into 50mL of propionic acid, reflux at 145~150℃ for 1.5~2h, after the end of the reaction, lower the temperature Reduce to 90~100°C, distill off propionic acid under reduced pressure, evaporate to dryness, dissolve with chloroform, add 5% sodium bicarbonate solution to adjust pH to alkaline, extract with chloroform-5% sodium bicarbonate, collect The organic layer was dried with anhydrous sodium sulfate, filtered, and the reaction solution was concentrated by rotary evaporation to obtain a crude product; the crude product was placed on the top of neutral alumina (diameter 5cm×length 15cm), eluted with dichloromethane, and the first layer of purple was collected. The red layer was evaporated to dryness to obtain the purple powder product 5,10,15,20-tetrakis(3-cyano)phenylporphyri...

Embodiment 2

[0050] 1. Synthesis of phenylcadmium porphyrin——5,10,15,20-tetrakis(3-tetrazolyl)phenylcadmium porphyrin

[0051] (1), (2) are the same as embodiment one;

[0052] (3) Dissolve 5,10,15,20-tetrakis(3-tetrazolyl)phenylporphyrin (0.4mmol, 0.35g) in anhydrous DMF (20mL), add Cd(OAc) 2 2H 2 O (2mmol, 0.533g), refluxed for 4~5 hours, cooled to room temperature, evaporated to dry DMF, washed several times with water-dichloromethane solution to obtain the product 5,10,15,20-tetrakis(3-tetrazolyl) The crude product of phenyl cadmium porphyrin, the crude product was separated by silica gel column chromatography to obtain the final product of dark green powder, the yield: 58%.

[0053] Its structure is as follows:

[0054]

[0055] 2. Preparation of the dye-sensitized solar cell: the preparation method is the same as in Example 1.

[0056] The performance of the battery: the curve of the relationship between the current density and the voltage of the dye-sensitized solar cell is s...

Embodiment 3

[0058] 1. Synthesis of phenylcobalt porphyrin - 5,10,15,20-tetrakis(3-tetrazolyl)phenylcobalt porphyrin

[0059] (1), (2) are the same as embodiment one;

[0060] (3) Dissolve 5,10,15,20-tetrakis(3-tetrazolyl)phenylporphyrin (0.4mmol, 0.35g) in anhydrous DMF (20mL), add Co(OAc) 2 2H 2 O (2mmol, 0.498g), refluxed for 4~5 hours, cooled to room temperature, evaporated to dry DMF, washed several times with water-dichloromethane solution to obtain the product 5,10,15,20-tetrakis(3-tetrazolyl) The crude product of phenylcobalt porphyrin was separated by silica gel column chromatography to obtain the final product as a dark green powder with a yield of 53%.

[0061] Its structure is as follows:

[0062]

[0063] 2. Preparation of the dye-sensitized solar cell: the preparation process is the same as in Example 1.

[0064] Performance of Dye-Sensitized Solar Cells: Curves of Current Density vs. Voltage See Figure 4 : J is 0.435mA / cm 2 , V is 363mV, and the maximum value of IP...

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Abstract

The invention discloses synthesis of tetrazole porphyrin metal complexes and applications of the metal complexes as dye sensitizing agents for preparation of dye-sensitized solar cells. Tetrazole is good in photoluminescence performance and is introduced into a porphyrin ring through conjugated chemical bonds, thus largely improving luminescence performance of porphyrin molecules. Four meta-position tetrazole groups of tetrazole porphyrin are bonded to TiO2 in a horizontal bonding manner. Introduction of a metal changes orbital energy level distribution, thus increasing the electron transfer efficiency and further increasing the photoelectric conversion efficiency. Compared with traditional ruthenium dye, raw materials are simple and easily available, precious metal materials are not needed, and pollution to the environment is low. Accordingly, the tetrazole porphyrin metal complexes can be adopted as dye sensitizing agents and used for preparation of dye-sensitized solar cells. Results of photoelectric property tests show that the tetrazole complexes with different metals in the dye-sensitized solar cells have certain current outputting capabilities and have different photoelectric conversion efficiencies under standard illumination.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and relates to a synthesis method of a porphyrin tetrazolium metal complex, and also relates to the use of the porphyrin tetrazolium metal complex as a dye sensitizer in the preparation of a dye-sensitized solar cell application. Background technique [0002] With the growing economy and population, energy crisis and environmental pollution are urgent problems facing mankind, we must look for a green renewable energy. Solar energy is a widely distributed, safe and environmentally friendly renewable energy. Therefore, utilizing and converting solar energy resources is a hot topic nowadays. At present, solar cells on the market mainly use silicon semiconductor materials, but due to its high cost and serious pollution, it is necessary to develop new energy sources. Dye-sensitized solar cells have been a research hotspot in recent years. The highest photoelectric conversion efficiency o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/22H01G9/20
CPCY02E10/542C07D487/22H01G9/2059
Inventor 刘家成武彧郭文博
Owner NORTHWEST NORMAL UNIVERSITY
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