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Application of porphyrin-based covalent organic framework material in photocatalytic oxidation cyclization reaction

A technology of covalent organic framework and photocatalytic oxidation, applied in the photocatalytic oxidative cyclization reaction, based on the field of covalent organic framework materials of porphyrin, can solve the problem that photosensitizers cannot be recycled repeatedly, and the structure synthesis is difficult. Molecules, increase costs and other issues, achieve high universality and repeatability, do not reduce activity, and increase cost effects

Active Publication Date: 2021-10-26
SHANDONG NORMAL UNIV
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  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] It is known in the prior art that most of the photosensitizers used in photocatalytic organic reactions at this stage are metal-organic compounds with relatively complex structures and small organic molecules that are difficult to synthesize; The faster reaction rate will lead to more by-products in the reaction itself, and the photosensitizer cannot be recycled repeatedly; the metals used in the metal-organic compounds used as photosensitizers are mostly noble metals, which greatly increases the cost of the reaction

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  • Application of porphyrin-based covalent organic framework material in photocatalytic oxidation cyclization reaction
  • Application of porphyrin-based covalent organic framework material in photocatalytic oxidation cyclization reaction
  • Application of porphyrin-based covalent organic framework material in photocatalytic oxidation cyclization reaction

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preparation example Construction

[0042] In one embodiment of the present invention, a method for synthesizing N-methyltetrahydro-1H-pyrrolo[3,4-c]-quinoline-1,3(2H)-dione derivatives is provided, The synthetic method comprises the following steps:

[0043] 1) adding N,N-dimethylaniline derivatives and maleimide derivatives into an organic solvent to obtain solution A;

[0044] 2) adding a metal-free covalent organic framework material based on a porphyrin structure as a photocatalyst into solution A to obtain solution B;

[0045] 3) Irradiate solution B with visible light to obtain N-methyltetrahydro-1H-pyrrolo[3,4-c]-quinoline-1,3(2H)-dione derivative.

[0046]

[0047] The technical problem to be solved in this embodiment of the present invention is to use a metal-free covalent organic framework material based on a porphyrin structure as a photocatalyst to catalyze the oxidative cyclization of N,N-dimethylaniline and maleimide through visible light reaction to construct N-methyltetrahydro-1H-pyrrolo[3,...

Embodiment 1

[0063] Synthesis of porphyrin-based covalent organic framework materials H 2 p-Bph-COF:

[0064] Metal-free 5,10,15,20-tetrakis(4-aminophenyl)porphyrin (H 2 TAPP) (32.38 mg, 0.05 mmol) and o-dichlorobenzene / n-butanol (3 / 1 by volume; 1 mL) were passed through three free pump-thaw cycles, and 4, 4-Biphenyldicarbaldehyde (21.02 mg, 0.10 mmol) was degassed; the tube was sealed and heated at 120°C for 3 days. The precipitate was collected by filtration, washed with anhydrous THF and acetone, and dried under vacuum at 120 °C overnight.

[0065] from figure 1 It can be seen that H 2 p-Bph-COF has good crystallinity, H 2 In the PXRD pattern of p-Bph-COF, the strong diffraction peaks at 3.3° and 7.5° correspond to (1,0,0) and (0,1,0) crystal planes, respectively.

[0066] figure 2 a It can be seen that the absorption of this material is very wide. According to the energy gap conversion formula, the Eg=+1.75eV of the material is obtained, and the figure 2 -b The cyclic voltamm...

Embodiment 2

[0070] h 2 Synthesis of N-methyltetrahydro-1H-pyrrolo[3,4-c]-quinoline-1,3(2H)-dione by oxidative cyclization reaction catalyzed by p-Bph-COF:

[0071] N,N-Dimethylaniline (0.20 mmol, 2.0 eq), maleimide (0.10 mmol, 1.0 eq), H2p-Bph-COF (8 mg, 5 mol%) were placed in a pre-dried In a standard glass reaction tube, chloroform was added as a solvent, irradiated with a blue LED for 14 hours in an oxygen atmosphere, and then the catalyst was collected by centrifugation. The organic layer was separated, and the solvent was removed in vacuo, and purified by silica gel column chromatography (ethyl acetate / petroleum ether=1 / 3, v / v) to obtain the product N-methyltetrahydro-1H-pyrrolo[3,4 -c]-quinoline-1,3(2H)-dione. The yield of product obtained was 70%. H NMR, C NMR, and mass spectrometry identified the product as N-methyltetrahydro-1H-pyrrolo[3,4-c]-quinoline-1,3(2H)-dione.

[0072] The hydrogen spectrum and carbon spectrum of the product N-methyltetrahydro-1H-pyrrolo[3,4-c]-quinoli...

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Abstract

The invention relates to the technical field of catalytic synthesis, and concretely relates to application of a porphyrin-based covalent organic framework material in photocatalytic oxidation cyclization reaction. The structure of the porphyrin-based covalent organic framework material is as shown in formula I. A synthesis method of an N-methyltetrahydro-1H-pyrrolo[3, 4-c]-quinoline-1, 3(2H)-dione derivative comprises the following steps: adding an N, N-dimethylaniline derivative and a maleimide derivative into an organic solvent to obtain a solution A; adding the material in the formula I into the solution A to obtain a solution B; and irradiating the solution B with visible light to obtain a product. A metal-free covalent organic framework based on a porphyrin structure is used as a photosensitizer, oxygen is used as an oxidizing agent, an oxidative cyclization reaction of the N, N-dimethylaniline derivative and the maleimide derivative is realized under the irradiation of visible light, and the tetrahydroquinoline compound is efficiently constructed; and the method is green and mild in condition, the photosensitizer can be recycled, the utilization rate of the photosensitizer is increased, the cost is reduced, and industrial popularization and application are facilitated.

Description

technical field [0001] The invention relates to the technical field of catalytic synthesis, in particular to the application of porphyrin-based covalent organic framework materials in photocatalytic oxidative cyclization reactions. Background technique [0002] The information disclosed in this background section is only intended to increase the understanding of the general background of the present invention, and is not necessarily taken as an acknowledgment or any form of suggestion that the information constitutes the prior art already known to those skilled in the art. [0003] Tetrahydroquinoline is an important structural unit present in many natural products and synthetic drugs, and has a wide range of biological activities, such as antibacterial, neuroprotective, antiarrhythmic, etc. Due to the importance of their structure, the synthesis of tetrahydroquinolines has always been the research focus of chemists. N-Methyltetrahydro-1H-pyrrolo[3,4-c]-quinoline-1,3(2H)-di...

Claims

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Application Information

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IPC IPC(8): B01J31/06C07D471/04
CPCB01J31/06C07D471/04B01J2231/70B01J35/39
Inventor 董育斌李鑫雨吴成娟耿琰
Owner SHANDONG NORMAL UNIV
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