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Macrocyclic carrier multi-center metalloporphyrin complex and preparation method of polycarbonate

A metalloporphyrin, multi-center technology, applied in the field of preparation of macrocyclic carrier multi-center metalloporphyrin complexes and polycarbonate, can solve problems such as being difficult to meet market demands

Active Publication Date: 2020-08-25
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, it is still difficult to meet the market demand

Method used

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  • Macrocyclic carrier multi-center metalloporphyrin complex and preparation method of polycarbonate
  • Macrocyclic carrier multi-center metalloporphyrin complex and preparation method of polycarbonate
  • Macrocyclic carrier multi-center metalloporphyrin complex and preparation method of polycarbonate

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preparation example Construction

[0079] The present invention to the described The preparation method of is not particularly limited, and may be commercially available, or prepared according to methods well known to those skilled in the art.

[0080] Preferably in the present invention, the The specific preparation method is:

[0081] The p-hydroxybenzaldehyde, substituted benzaldehyde, and pyrrole were subjected to a "one-pot" reaction under the condition of propionic acid reflux, and the second color band was collected by column chromatography separation technology to obtain a monohydroxyl substituted asymmetric porphyrin; the central metal M and the co-ligated Body X is coordinated to the porphyrin ring through the metallation reaction of the porphyrin ligand in dichloromethane solution; The reaction to synthesize ethers takes place under neutral conditions.

[0082] said for linking groups.

[0083] Preferably, the It has the structure shown in formula III-a or formula III-b:

[0084]

[008...

Embodiment 1

[0101]

[0102] A mixture of p-tert-butylphenol (4.0g, 26.6mmol), sodium hydroxide (NaOH) (1g) and formaldehyde (2.0ml, 71.2mmol) solution was placed in an open container in a microwave synthesizer (CEM) Irradiate with 100w power and stir for 3min. Cooling for 10 minutes gave a yellow solid. Add 4ml of toluene and 30ml of diphenyl ether, and then irradiate with 100W microwave power for 5 minutes under stirring to obtain a dark brown solution. This solution was added to 75 ml of ethyl acetate and allowed to stand for 2 hours. Filtration and washing with ethyl acetate, drying afforded the product EL1. The yield is about 80%. 1 HNMR: (DMSO, ppm) 1.1,3.8,7.1,9.7, high-resolution electrospray mass spectrometry analysis, analysis result is [C 44 h 56 o 4 ]: 648.42, found: 648.37.

[0103] Add 15g (120mmol) of 3-hydroxybenzaldehyde, 68.1g (370mmol) of 4-bromobenzaldehyde and 33g (490mmol) of pyrrole into 500mL of propionic acid, heat up to about 130°C, reflux for 1.5h, and ...

Embodiment 2

[0108]

[0109] 10 g (15.4 mmol) of EL1 and 8.8 g of phenol were dissolved in 200 mL of toluene. Add 16g (120mmol) of AlCl 3 , and the mixture was stirred at 60 °C for 6 h. After cooling, 200 mL of HCl (3%, v / v) was added, and the reaction mixture was stirred for 30 minutes. The aqueous phase was washed once with toluene, and the organic phase was washed with Na 2 SO 4 Dry, then remove toluene by rotary evaporation. 100mL CH 3 OH was added to the semi-solid residue. After filtration and drying, a white residue was obtained, which was washed with CHCl 3 / CH 3 Recrystallization from OH afforded 5.8 g of EL5 in about 87% yield. 1 H NMR (CDCl 3 , ppm): 10.2, 7.0, 6.7, 4.2, 3.5. High-resolution electrospray mass spectrometry analysis, the analysis result is [C 28 h 24 o 4 ]: 424.17, found: 424.09.

[0110] Under the protection of nitrogen, 2.03g (1.97mmol) EL3, 0.21g (0.49mmol) EL5, 0.12g potassium carbonate and 0.01g potassium iodide were dissolved in 200mL anhydr...

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Abstract

The invention provides a macrocyclic carrier multi-center metalloporphyrin complex. The macrocyclic carrier multi-center metalloporphyrin complex has a structure shown as a formula I. According to themulti-center metalloporphyrin complex, the porphyrin complex can be prepared by connecting porphyrin to calixarene with a specific group; the porphyrin complex containing a plurality of active centers can be rapidly prepared according to the scheme; compared with the prior art, the macrocyclic carrier multi-center metalloporphyrin complex has advantages that the number of the active centers is determined and can be adjusted through the size of a calixarene ring, and the spatial conformation can be adjusted and controlled by changing a calixarene substituent group. The catalyst shows high catalytic activity, product selectivity and high-temperature stability when catalyzing copolymerization of carbon dioxide and alkylene oxide.

Description

technical field [0001] The invention relates to the technical field of catalysts, in particular to a method for preparing a macrocyclic carrier multi-center metal porphyrin complex and polycarbonate. Background technique [0002] Degradable materials have been widely concerned by researchers and the whole society, and carbon dioxide is not only a greenhouse gas, but also a carbon-oxygen resource that is abundant, cheap and easy to obtain, non-toxic and harmless. Carbon dioxide and epoxide can be alternately copolymerized, and the product polycarbonate is fully degradable, and it also provides a good substitute for the increasingly scarce non-renewable resources such as petroleum. Polycarbonate has excellent transparency and excellent barrier properties, and can be used as engineering plastics, disposable medicine and food packaging materials, adhesives, etc. Taking propylene oxide as an example, its alternating polymerization product PPC can be used in agricultural mulch fi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/06C08G64/34
CPCC07F5/069C08G64/34
Inventor 张若禹曹瀚王献红
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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