Conjugated Schiff base Zn (zinc) porphyrin as well as preparation and application thereof

A technology of Schiff base and conjugation, which is applied in the field of Schiff base conjugated Zn porphyrin compound and its synthesis, can solve the problems of limited resources and large-area use restrictions, and achieve low environmental pollution, low cost, and mild reaction conditions Effect

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

AI Technical Summary

Problems solved by technology

However, ruthenium is a rare and precious metal with limited resources, and its large-scale application is restricted.

Method used

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  • Conjugated Schiff base Zn (zinc) porphyrin as well as preparation and application thereof
  • Conjugated Schiff base Zn (zinc) porphyrin as well as preparation and application thereof
  • Conjugated Schiff base Zn (zinc) porphyrin as well as preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Embodiment 1, the synthesis of organic dye (1)

[0039] (1) Synthesis of 5,10,15,20-tetrakis(p-nitrophenyl)porphyrin

[0040] Add 4.0050g (26mmol) of p-nitrobenzaldehyde to 70ml of nitrobenzene, add 1.86ml (26mmol) of pyrrole, and when the temperature of the system reaches 180°C, inject 2.25ml (27mmol) of L-lactic acid and react for 2 hours. Cool to room temperature, add 30ml methanol and stir for 0.5h, place in the refrigerator, filter after 12h, wash the filter cake with methanol and acetone to get 5,10,15,20-tetrakis(p-nitrophenyl)porphyrin, the yield 19%.

[0041] (2) Synthesis of 5,10,15,20-tetrakis(p-aminophenyl)porphyrin

[0042] Dissolve 1.4556g (1.82mmol) of 5,10,15,20-tetrakis(p-nitrophenyl)porphyrin in 60ml of concentrated hydrochloric acid, add 5.8224g (25mmol) of stannous chloride in concentrated hydrochloric acid solution under the protection of argon , reacted in a water bath at 65°C for 1 h, changed to an ice bath for another 0.5 h, neutralized with a...

Embodiment 2

[0048] The synthesis of embodiment 2, organic dye (1)

[0049] Steps (1), (2), (3) are the same as in Example 1

[0050] (4) Synthesis of 5,10,15,20-tetrakis[(4-(2-pyridinealdehyde-benzimine)]-based zinc porphyrin (organic dye (1))

[0051] Dissolve 0.0677g (0.0884mmol) of 5,10,15,20-tetrakis(p-aminophenyl)zinc porphyrin and 0.7952mmol of 2-pyridinecarbaldehyde in 20ml of N,N-dimethylformamide under argon atmosphere Under protection, react at 80°C for 24h; after the reaction, cool to room temperature, add water and filter to obtain the crude product, wash the filter cake with water and methanol successively, and dry to obtain 5,10,15,20-tetrakis[(4-(2-pyridine Aldehyde-benzimine)] base zinc porphyrin, the productive rate is 49%.

[0052] The proton nuclear magnetic spectrum data are with embodiment 1.

Embodiment 3

[0053] Embodiment 3, the synthesis of organic dye (1)

[0054] Steps (1), (2), (3) are the same as in Example 1

[0055] (4) Synthesis of 5,10,15,20-tetrakis[(4-(2-pyridinealdehyde-benzimine)]-based zinc porphyrin (organic dye (1))

[0056] Dissolve 0.2257g (0.2946mmol) of 5,10,15,20-tetrakis(p-aminophenyl)zinc porphyrin and 2.6509mmol of 2-pyridinecarbaldehyde in 20ml of N,N-dimethylformamide under argon atmosphere Under protection, react at 80°C for 24h; after the reaction, cool to room temperature, add water and filter to obtain the crude product, wash the filter cake with water and methanol successively, and dry to obtain 5,10,15,20-tetrakis[(4-(2-pyridine Aldehyde-benzyl imine)] base zinc porphyrin, productive rate is 45%.Proton nuclear magnetic spectrum data are with embodiment 1.

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Abstract

The invention provides a conjugated Schiff base Zn (zinc) porphyrin compound, and belongs to the technical field of chemical synthesis. In the preparation method, porphyrin compound is made from nitrobenzaldehyde and pyrrole by four reaction steps of condensation, reduction, coordination and substitution. Because of a large conjugated system of Schiff base and porphyrin, the sunlight absorptivity of the porphyrin compound is improved, the maximum IPCE (incident photon-to-electron conversion efficiency) value can reach 25%, and the photoelectric conversion efficiency Eta also reaches 0.40, thus the conjugated Schiff base Zn porphyrin compound has good application prospect in preparation of a dye sensitized solar cell. Compared with the traditional ruthenium dye, the obtained conjugated Schiff base Zn porphyrin compound has the advantages that raw materials are cheap and obtained easily, synthetic process is simple, reaction condition is mild, no expensive metal raw material is used, and the effects of low cost, high yield and less environmental pollution are achieved.

Description

technical field [0001] The invention provides a Schiff base conjugated Zn porphyrin compound and a synthesis method thereof, and also relates to the application of the Schiff base conjugated Zn porphyrin compound as a photosensitizer in preparing sensitized solar cell electrodes. Background technique [0002] As a new energy utilization device, dye-sensitized solar cells are the most promising renewable energy sources. At present, the dye sensitizers with the highest efficiency are ruthenium complexes containing porphyrin and polypyridine (the efficiency reaches 11%). However, ruthenium is a rare and precious metal with limited resources, and its large-scale application is restricted. Among all organic dyes, porphyrin and its derivatives can promote the sensitization of semiconductor materials (TiO2) due to their strong Soret band absorption and Q band absorption at 400~450nm and 500~650nm. 2 ) are responded in the visible range. Due to its easy design and chemical modifi...

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 刘家成梁莉莉曹靖
Owner NORTHWEST NORMAL UNIVERSITY
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