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Pyrene tetrone bridging molecular tweezers-series metalloporphyrin compound and preparation method thereof

A technology of porphyrin compounds and metalloporphyrins, applied in organic chemistry and other directions, can solve problems such as unfavorable separation and purification, affecting photoelectric effect, unfavorable electron transfer, etc., and achieves the effects of good solubility, improved photoelectric performance, and improved photoelectric conversion efficiency.

Inactive Publication Date: 2015-05-27
BEIJING INSTITUTE OF TECHNOLOGYGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, tetraphenylporphyrin is mainly modified to obtain new photoelectric materials, but there are generally solubility problems, and many by-products will be generated during the modification process, which is not conducive to separation and purification.
In terms of porphyrin linking, it is mainly realized through amide bonds, acid anhydride bonds and adipic acid, which have a great impact on the planarity of molecules, which is not conducive to electron transfer, thus affecting its photoelectric effect

Method used

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  • Pyrene tetrone bridging molecular tweezers-series metalloporphyrin compound and preparation method thereof
  • Pyrene tetrone bridging molecular tweezers-series metalloporphyrin compound and preparation method thereof
  • Pyrene tetrone bridging molecular tweezers-series metalloporphyrin compound and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0046] The preparation method of pyrene tetraketone bridged molecular tweezers copper porphyrin compound comprises the following steps:

[0047] (1) Synthesis of porphyrin

[0048] Add 180mL propionic acid and 15g 3,5-di-tert-butylbenzaldehyde to a 500mL round-bottomed flask successively, heat to a slight boil; add 25mL 0.2g / mL pyrrole propionic acid solution dropwise, stir and reflux for 1h; Add 150mL of methanol to the reaction solution for recrystallization, let it stand, and filter to obtain a purple solid, which is porphyrin.

[0049] (2) Synthesis of nitrocopper porphyrin

[0050] Add 180mL chloroform and 800mg porphyrin to a 500mL round bottom flask successively, heat to boiling, add 10mL 25g / L copper acetate methanol solution, reflux and stir for 1h to obtain a copper porphyrin solution; dissolve 250mg copper nitrate in 20mL acetic acid and Add the copper porphyrin solution to the mixed solution obtained by 50 mL of propionic anhydride, and stir under reflux for 10 min...

Embodiment 2

[0058] The preparation method of pyrene tetraketone bridged molecular tweezers nickel porphyrin compound comprises the following steps:

[0059] (1) Synthesis of porphyrin

[0060] Add 180mL propionic acid and 13.5g 3,5-di-tert-butylbenzaldehyde to a 500mL round-bottomed flask in turn, heat to a slight boil; add dropwise 30mL 0.17g / mL pyrrole propionic acid solution, stir and reflux for 0.5h; Add 135mL of methanol to the reaction solution for recrystallization, let it stand, and filter to obtain a purple solid, which is porphyrin.

[0061] (2) Synthesis of nitrocopper porphyrin

[0062] Add 150mL chloroform and 600mg porphyrin to a 500mL round-bottom flask in turn, heat to boiling, add 10mL 20g / L methanol solution of copper acetate, reflux and stir for 0.5h to obtain a copper porphyrin solution; dissolve 200mg copper nitrate in 30mL acetic acid In the mixed solution obtained with 50mL propionic anhydride, add copper porphyrin solution, reflux and stir for 5 minutes. Cool to...

Embodiment 3

[0074] The preparation method of pyrene tetraketone bridged molecular tweezers palladium porphyrin compound comprises the steps:

[0075] (1) Synthesis of porphyrin

[0076] Add 180mL propionic acid and 14g 3,5-di-tert-butylbenzaldehyde to a 500mL round-bottomed flask in turn, heat to a slight boil; add dropwise 36mL 0.24g / mL pyrrole propionic acid solution, stir and reflux for 2h; Add 200mL of methanol to the solution for recrystallization, let it stand, and filter to obtain a purple solid, which is porphyrin.

[0077] (2) Synthesis of nitrocopper porphyrin

[0078] Add 150mL chloroform and 700mg porphyrin to a 500mL round bottom flask successively, heat to boiling, add 13mL 35g / L copper acetate methanol solution, reflux and stir for 2h to obtain a copper porphyrin solution; dissolve 300mg copper nitrate in 40mL acetic acid and Add the copper porphyrin solution to the mixed solution obtained by 50 mL of propionic anhydride, and stir under reflux for 10 min. Cool to room te...

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Abstract

The invention discloses a pyrene tetrone bridging molecular tweezers-series metalloporphyrin compound and a preparation method thereof, and belongs to the field of photoelectric conversion materials. A molecular formula of the compound is C182H202N12M2, and a structural formula of the compound is shown in the specification. The preparation method comprises the following steps: reacting 3,5-di-tert-butyl benzaldehyde with pyrrole to obtain porphyrin; reacting trichloromethane, porphyrin and copper acetate to obtain a solution a, adding a copper acetate solution into the solution a, and reacting to obtain copper nitryl porphyrin; reacting copper nitryl porphyrin with 4-amino-1,2,4-triazole to obtain amino-substituted copper nitryl porphyrin; reacting amino-substituted copper nitryl porphyrin, palladium / carbon and sodium borohydride to obtain diamino copper porphyrin; reacting diamino copper porphyrin with 2,7-di-tert-butyl pyrene-4,5,9,10-tetraone to obtain a compound 1; reacting the compound 1, trifluoroacetic acid and concentrated sulfuric acid to obtain the pyrene tetrone bridging molecular tweezers-series metalloporphyrin compound; reacting the pyrene tetrone bridging molecular tweezers-series metalloporphyrin compound with a methanol solution of metal acetate to obtain the compound.

Description

technical field [0001] The invention relates to a metalloporphyrin compound of a pyrenetetraketone bridged molecular tweezers series and a preparation method thereof, belonging to the field of photoelectric conversion materials. Background technique [0002] Porphyrin compounds have good light, thermal and chemical stability, and have strong characteristic electronic absorption spectra in the visible light region. In recent years, the design and synthesis of optoelectronic functional materials and devices using the unique electronic structures and optoelectronic properties of porphyrin and its complexes has become a very active research field in the world. At present, tetraphenylporphyrin is mainly modified to obtain new photoelectric materials, but there are generally solubility problems, and many by-products will be generated during the modification process, which is not conducive to separation and purification. In terms of porphyrin linking, it is mainly realized through...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/22
CPCC07D487/22
Inventor 张汝波王华栋黄学斌
Owner BEIJING INSTITUTE OF TECHNOLOGYGY