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Preparation method and application of polypyridyl functional group modified porphyrin TTPP

A technology of functional groups and polypyridines, which is applied in the field of preparation of porphyrin TTPP modified by polypyridine functional groups, can solve the problems of cumbersome, difficult separation of synthesis methods, and inability to meet the coordination requirements of metal ions, and achieve simple process and high efficiency. High, improve the effect of relative quantum yield

Inactive Publication Date: 2019-10-15
UNIV OF SCI & TECH BEIJING
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there are few reports on the assembly of this molecule with a metal to obtain a two-dimensional metal framework structure, because the porphyrin molecule cannot meet the coordination requirements of metal ions when forming a two-dimensional organometallic framework structure.
By introducing polypyridine groups in the 5, 10, 15, and 20 positions of porphine, porphyrin molecules for assembling two-dimensional metal framework structures can be obtained. However, the synthesis of such molecules is still cumbersome so far, especially Late isolation difficulties due to flaws in the synthesis method

Method used

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  • Preparation method and application of polypyridyl functional group modified porphyrin TTPP
  • Preparation method and application of polypyridyl functional group modified porphyrin TTPP
  • Preparation method and application of polypyridyl functional group modified porphyrin TTPP

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Experimental program
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Effect test

Embodiment 1

[0036] Preparation of TTPP:

[0037] Dissolve 1.7g, 5.0mmol (one equivalent) of 4'-(4-formylphenyl)-2,2':6',2'tripyridine in 50mL (per 1.0mmol 4'-(4-formyl Phenyl)-2,2':6',2'tripyridine corresponding to 10.0mL solvent) in propionic acid, reflux; 0.34mL, 5.0mmol (double equivalent) pyrrole propionic acid solution 5mL (per 1.0mmol pyrrole Corresponding to 1.0mL solvent) was slowly added dropwise, and refluxed for 1h; after the reaction system was cooled to room temperature, the reaction mixture was slowly poured into 200mL water; stood at 0°C until the precipitation was complete, and then suction filtered to obtain a purple precipitate, which was washed with methanol Slow washing to neutral (pH=7) and then slow washing with chloroform to free starting material gave the final product in 25% yield. The synthesis process of porphyrin molecule is shown in figure 1 .

[0038] For the synthesis of the porphyrin precursor 4'-(4-formylphenyl)-2,2':6',2'tripyridine, see the method de...

Embodiment 2

[0040] Assembly and application of TTPP:

[0041] The assembly method adopts Langmuir-Blodgett technology, which can assemble porphyrin and metal ions at the gas-liquid interface. The resulting structure is a metal-organic framework (MOF) nanosheet (Ni-TTPP), which has a structure similar to single-layer graphene with large holes. The assembly structure can be used as the photoanode of solar cells to construct solar cells, and due to the ordered structure of MOF nanosheets, there are holes, and its function can be adjusted by adding guests.

[0042] The specific process of the above-mentioned Langmuir-Blodgett technique is: NiCl with a concentration of 1mM 2 The aqueous solution is a subphase, and 150 μL of TTPP chloroform solution (6.5×10 -5 M), slowly drop on the gas-liquid interface (500cm 2 ). Keep at room temperature for 30 minutes, and press the barrier at a speed of 35mm / min until the surface tension is 5mN / m. Then use ITO as the substrate, transfer the assembled n...

Embodiment 3

[0046] Experimental Study:

[0047] In order to verify the beneficial effects of the present invention, the inventor has carried out a large amount of experimental research, and part experimental process and result are as follows:

[0048] Characterization of porphyrin molecules: The synthesized porphyrin molecules were subjected to mass spectrometry, NMR, and elemental analysis to illustrate the structure and purity of the synthesized molecules. See the results at the end of the article and Figure 4 .

[0049] Structural assembly: eg figure 2 As shown, the concentration of TTPP used in the assembly experiment was 0.1mg / ml (6.5×10 -5 M) in chloroform solution. In a clean room, clean the surface of Langmuir & Langmuir Blodgett membrane analyzer with absorbent cotton soaked in ethanol or chloroform, NiCl 2 (1.0 mM) aqueous solution as a subfill analyzer tank. Then, 150 μL of 0.1 mg / ml TTPP chloroform solution (the volume of the TTPP chloroform solution taken is proportion...

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Abstract

The invention relates to the technical field of synthesis and application of polypyridyl porphyrins, and provides a preparation method and an application of a polypyridyl functional group modified porphyrin TTPP. The preparation method comprises the following steps: dissolving 4'-(4-formylphenyl)-2,2':6',2'-tripyridine in propionic acid, and performing heating; slowly dropwise adding the propionicacid solution of pyrrole, and performing refluxing; slowly pouring a reaction mixture obtained after the reaction system is cooled into water; standing the obtained system, and performing suction filtration to obtain a purple precipitate; and respectively slowly washing the purple precipitate with chloroform and methanol to obtain the final product. The polypyridyl functional group-modified porphyrin TTPP can be assembled to produce a photoanode device and a solar cell. A uniform, dense, ordered and porous two-dimensional MOF nanosheet similar to a graphene structure can be obtained, the assembled structure is successfully applied to the solar cell as the photoanode of the solar cell, and a guest molecule fullerene is introduced in the assembled structure to improve the performances to some extent.

Description

technical field [0001] The invention relates to the technical field of synthesis and application of polypyridine porphyrin, in particular to a preparation method and application of polypyridine functional group modified porphyrin TTPP. Background technique [0002] Porphyrin is a general term for homologues and derivatives with substituents on the outer ring of porphyrin. Porphyrin is a rigid coplanar molecule composed of a central 18-π electron conjugated system and has aromaticity. The 2, 3, 7, 8, 12, 13, 17, 18 and meso-positions (5, 10, 15, 20 middle positions of the porphyrin molecule) around the porphyrin molecule can be replaced by other substituents; the center can be almost identical to All metal ions in the periodic table, including rare earth elements, are coordinated; this characteristic of having multiple modifiable positions and being easy to complex metal ions greatly enriches the diversity of porphyrin molecules. In natural molecules, such as human heme and ...

Claims

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Application Information

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IPC IPC(8): C07D487/22C09B47/08C08G83/00H01G9/20
CPCC07D487/22C08G83/008C09B47/08H01G9/20
Inventor 刘晨曦王海龙姜建壮
Owner UNIV OF SCI & TECH BEIJING
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