Novel porphyrin ligand and metal complex, preparation method and application for novel porphyrin ligand

A technology of metal complexes and porphyrins, applied in chemical instruments and methods, photosensitive equipment, porphine/acridine porphine, etc., to achieve the effect of cheap and easy-to-obtain raw materials and mild conditions

Active Publication Date: 2012-12-19
XIAN RUILIAN NEW MATERIAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The advantage of the Adler method is that it is easy to operate, the reaction conditions are not harsh, and more than 70 kinds of porphyrin compounds can be prepared, but it is difficult to form the corresponding porphyrins for acid and heat unstable aldehydes by this method.

Method used

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  • Novel porphyrin ligand and metal complex, preparation method and application for novel porphyrin ligand
  • Novel porphyrin ligand and metal complex, preparation method and application for novel porphyrin ligand
  • Novel porphyrin ligand and metal complex, preparation method and application for novel porphyrin ligand

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Embodiment Construction

[0025] 1. Synthesis of TCPP-Me.

[0026]

[0027] In a 250mL three-neck flask equipped with a condenser, a mechanical stirrer and a constant pressure funnel, add 6.56g of methyl 4-formylbenzoate and 80mL of n-propionic acid in sequence, start stirring, then heat to reflux (132°C), pass Slowly add the mixed solution of 2.72g pyrrole and 8ml acetic anhydride to the system through the constant pressure dropping funnel (about 25 minutes to complete the dropwise addition). During the dropping process, the color of the reaction solution changes from light yellow to dark brown. After 3h, the reaction was stopped, and after cooling down to room temperature, it was placed in the refrigerator to freeze overnight.

[0028] Post-processing: filter the reaction solution, rinse the filter cake with 100ml ethanol, dry the solid to obtain 2.06g of blue-purple solid, and characterize the molecular structure by 1HNMR and MS, which is the product TCPP-Me, yield: 21% .

[0029] 2. Synthesis ...

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Abstract

The invention relates to a novel porphyrin ligand and a metal complex, a preparation method and application for the novel porphyrin ligand. The complex has potential application values in fields of dye sensitization solar cells, organic catalytic chemistry, material chemistry and the like. Firstly, 4-formoxyl methyl benzoate and pyrrole serve as raw materials to synthesize TCPP-Me, TCPP is obtained by hydrolyzing the TCPP-Me, one of a Tyr4-TCPP, a Tyr3-TCPP, a Tyr2-TCPP-1, a Tyr2-TCPP-2 and Tyr-TCPP is obtained by reacting the TCPP and tyrosine ethyl ester, and finally each ligand is reacted with corresponding metal salt to respectively obtain complexes corresponding to the ligand and the metal salt. A Tyr3-TCPP-Zn (II) shows a high open-circuit voltage in an application of a DSSC aspect.

Description

technical field [0001] The invention relates to a novel porphyrin ligand, its metal complex, its preparation method and application. Background technique [0002] Porphyrin is a general term for a class of macrocyclic compounds with substituents on the porphine ring, and has a special rigid π-electron delocalized structure. In the porphyrin macrocycle, the four nitrogen atoms constitute an environment with certain spatial positions and coordination capabilities, which can form stable complexes with metals. If the substituents are changed on the porphyrin ring, the electron-donating ability of the four nitrogen atoms is adjusted, different central metal ions are introduced, or axial ligands with different nucleophilicities are changed, the porphyrin and metalloporphyrin will have different properties, and therefore have different functions. Therefore, porphyrins and metalloporphyrins are widely used in the fields of solar cell materials, conductive materials, energy chemist...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/22H01G9/20
CPCY02E10/542C09B47/00Y02P70/50
Inventor 张立龙郭艳云刘小民王建文刘骞峰金立诺余勇杨燕
Owner XIAN RUILIAN NEW MATERIAL CO LTD
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