Acylhydrazone zinc protoporphyrin, and synthesis and application of complex thereof

A technology of porphyrin complexes and porphyrin compounds, applied in porphine/acridine porphine, chemical instruments and methods, electrolytic capacitors, etc., can solve the problems of low conversion efficiency of porphyrin photosensitive dyes, and achieve good photoelectric performance and environmental protection Low pollution, simple and easy-to-obtain raw materials

Inactive Publication Date: 2012-04-18
NORTHWEST NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The object of the present invention is to provide a kind of acylhydrazone zinc porphyrin and its complex against the defect of low conversion efficiency of porphyrin photosensitizing dyes in the prior art

Method used

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  • Acylhydrazone zinc protoporphyrin, and synthesis and application of complex thereof
  • Acylhydrazone zinc protoporphyrin, and synthesis and application of complex thereof
  • Acylhydrazone zinc protoporphyrin, and synthesis and application of complex thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0059] Embodiment 1, dyestuff I——5,10,15,20-tetra[(4-(2-pyridinecarbaldehyde-benzoylhydrazone)] base zinc porphyrin synthesis

[0060] (1) Freshly distilled pyrrole (15mmol, 1.04mL) and methyl 4-formylbenzoate (15mmol, 2.4624g) were stirred and dissolved in 1500mL of dichloromethane, and methanesulfonic acid (10.4mmol, 0.68mL) was added dropwise, React for 30 minutes, add dichlorodicyano-p-benzoquinone (13.2mmol, 3g), stir for 1 minute, then add 3mL triethylamine to neutralize methanesulfonic acid (MSA), make the pH of the system = 7.0, and the reaction is completed. Concentrate the reaction solution by rotary evaporation, install it on the upper end of a silica gel column (diameter 5cm×length 15cm), elute with dichloromethane containing 1% methanol until the solution is light brown, collect all eluted components, and concentrate by rotary evaporation; Put the concentrated solution on the upper end of a basic alumina column (diameter 5cm x length 12cm), elute with dichlorometh...

Embodiment 2

[0067] Embodiment 2, dye II——5,10,15,20-tetra[(4-(2-acetylbenzimidazole-benzoylhydrazone)] base zinc porphyrin synthesis

[0068] Steps (1), (2), and (3) are the same as in Example 1.

[0069] (4) Stir and dissolve 5,10,15,20-tetrakis(4-hydrazino)phenyl zinc porphyrin (0.4mmol, 0.3640g) in 35mL DMF; dissolve 2-acetylbenzimidazole (3.2mmol, 0.5128g) was dissolved in 45mL of ethanol at 60~70°C, then 1.5ml of glacial acetic acid (catalyst) was added dropwise, the two solutions were mixed under stirring, and the mixture was refluxed at 105°C. Followed by TLC, the reaction took 16 hours. After the reaction is completed, the solvent is removed, an appropriate amount of ether is added, and a large amount of purple-red precipitate is precipitated, filtered with suction, recrystallized with DMF-water (volume ratio 1:1), the green precipitate is collected, and dried at a constant temperature of 100°C to obtain the product dark purple powder II ——5,10,15,20-Tetrakis[(4-(2-acetylbenzimi...

Embodiment 3

[0074] Embodiment 3, dye III——5,10,15,20-tetra[(4-(salicylaldehyde-benzoylhydrazone)] base zinc porphyrin synthesis

[0075] Steps (1), (2), and (3) are the same as in Example 1.

[0076] (4) Stir and dissolve 5,10,15,20-tetrakis(4-hydrazino)phenyl zinc porphyrin (0.5mmol, 0.4550g) in 40mL DMF; dissolve salicylaldehyde (4mmol, 0.3908g) In 35 mL of ethanol, the two solutions were mixed under stirring, and the mixture was refluxed at 100°C. Followed by TLC, the reaction took 6 hours. After the reaction is complete, remove the solvent, add an appropriate amount of ether, let it stand still, and precipitate a large amount of purple precipitate, filter it with suction, recrystallize with acetone-ethanol (volume ratio 1:1), and collect the precipitated purple powder III——5,10,15,20- Tetra[(4-(salicylaldehyde-benzoylhydrazone)]-based zinc porphyrin. Yield 88%.

[0077] Its structure is as follows:

[0078]

[0079] The product is detected by a Varian nuclear magnetic resonance...

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Abstract

The invention discloses an acylhydrazone zinc protoporphyrin and a zinc and cobalt complex thereof, belonging to the field of chemical synthesis. In the acylhydrazone zinc protoporphyrin, an acylhydrazone structure and a porphyrin structure form a large conjugated system which can absorb a wider range of sunlight as compared with most of porphyrin dyes; and in the zinc and cobalt complex of the acylhydrazone zinc protoporphyrin, acylhydrazone zinc protoporphyrin molecules are connected to form a chain structure or high-dimensional structure, thereby improving the electron transfer efficiency and consequently improving the photoelectric conversion efficiency. Thus, the zinc and cobalt complex can be used as a dye sensitizer for the preparation of fuel-sensitive solar cells. Photoelectric property test results show that the fuel-sensitive solar cells prepared by the invention are capable of outputting a certain current to an external load and have different degrees of photoelectric conversion efficiency under the irradiation of standard light; and for the photocell using the zinc complex of the zinc protoporphyrin acylhydrazone as the dye, the maximum IPCE (Incident Photon to Current Efficiency) value is 13.4%.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and relates to a synthesis method of porphyrin compounds and their metal complexes, in particular to a synthesis method of acylhydrazone zinc porphyrin and its zinc and chromium complexes; Application of hydrazone zinc porphyrin and its zinc and chromium complexes as a dye sensitizer in the preparation of dye-sensitized solar cells. Background technique [0002] The energy crisis is an urgent problem facing human survival and development. Traditional energy sources such as coal, oil and wood can only last for fifty to one hundred years at the current rate of consumption. In addition, the resulting environmental pollution is also threatening the earth on which human beings depend for survival. Solar energy, as an inexhaustible, widely distributed, easy-to-use, and environmentally friendly renewable energy, is increasingly called for its development and utilization. Utilizing and conv...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/22C09B47/00H01G9/042H01G9/20H01L51/48H01L51/46
CPCY02E10/542Y02E60/13Y02E10/549C09B47/00C09B55/006H01G9/2059H10K85/381
Inventor 刘家成李蒙陈立伟曹靖郭国哲梁莉莉
Owner NORTHWEST NORMAL UNIVERSITY
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