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Polycarbazole-loaded nano-palladium material as well as preparation method and application thereof

A technology of nano-palladium and polycarbazole, applied in the field of catalytic chemistry, to achieve the effects of green and mild reaction conditions, wide application range and high conversion efficiency

Active Publication Date: 2019-02-12
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] In recent years, some research groups have used metal oxides as carriers to support palladium nanoparticles or palladium-gold alloys, but it is almost impossible to use polymers with visible light absorption as carriers to support palladium nanoparticles to achieve light-promoted reactions. The compounds mainly focus on aryl iodide and aryl bromide, but the visible light-induced reaction using aryl chloride as substrate has not been reported.

Method used

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  • Polycarbazole-loaded nano-palladium material as well as preparation method and application thereof
  • Polycarbazole-loaded nano-palladium material as well as preparation method and application thereof
  • Polycarbazole-loaded nano-palladium material as well as preparation method and application thereof

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Experimental program
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Effect test

Embodiment 1

[0051] Pd(OAc) 2 (11.2 mg), carbazole polymer (120 mg) were added to a 100 ml three-necked round bottom flask containing a magnetic stirrer, stirred at room temperature for 30 minutes, and then NaBH was added to it through a syringe 4 (0.05 M, 5.0 mL) aqueous solution, and reacted at room temperature for 4 hours; after the reaction, the solid was separated by centrifugation, washed with water, ethanol and ether in turn, and then vacuum-dried to obtain the corresponding polycarbazole-loaded nano-palladium material (Pd / P3,5-diCzPy).

[0052] ICP analysis indicated that the palladium loading was 1.37% wt.

[0053] Figure 1 to Figure 6 Followed by the powder XRD diffraction pattern, photoelectron energy spectrum, transmission electron microscope and particle size distribution, high-resolution transmission electron microscope and element distribution diagram of the palladium nanomaterial supported by the carbazole polymer of the present invention; the powder XRD diffraction pe...

Embodiment 2

[0055]

[0056] Add 4'-bromoacetophenone (40 mg), phenylboronic acid (37 mg), polycarbazole-supported nano-palladium material (8 mg), and potassium phosphate (64 mg) into a 10 ml quartz reaction tube equipped with a magnetic stir bar , add 5 ml of deionized water, repeat three times of liquid nitrogen freezing-pumping-nitrogen-filling-thawing, and then react at room temperature for 12 h under the irradiation of blue light LED; after the reaction, remove the catalyst by filtration, wash the catalyst with ethyl acetate, Extract the filtrate with ethyl acetate, combine the organic phases, dry, filter, concentrate under reduced pressure, and purify by silica gel column chromatography to obtain 4-biphenylethanone (yield 94%); using palladium carbon catalyst, the yield is 12% , adopting palladium chloride yield is 29%.

[0057] The NMR data of the resulting product are as follows:

[0058] 1 H NMR (600 MHz, CDCl 3 ) δ 8.03 (t, J = 6.9 Hz, 2H), 7.68 (dd, J = 7.5,6.3 Hz, 2H)...

Embodiment 3

[0064]

[0065] Add 4'-bromoacetophenone (40 mg), 4-methylphenylboronic acid (41 mg), polycarbazole-loaded nano-palladium material (8 mg), and potassium phosphate (64 mg) to a magnetic stirring bar 10 5 ml of deionized water was added to a quartz reaction tube, and the liquid nitrogen freezing-pumping-nitrogen filling-thawing was repeated three times, and then under the irradiation of a blue LED, the reaction was performed at room temperature for 12 h; after the reaction, the catalyst was removed by filtration, and the acetic acid Wash the catalyst with ethyl acetate, extract the filtrate with ethyl acetate, combine the organic phases, dry, filter, concentrate under reduced pressure, and purify by silica gel column chromatography to obtain 4'-methyl-4-biphenylphenone (98% yield) , if adopting diisopropylamine as the base, the yield is 16%.

[0066] The NMR data of the resulting product are as follows:

[0067] 1 H NMR (400 MHz, CDCl 3 ) δ 7.97 (d, J = 8.1 Hz, 2H), 7.62...

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Abstract

The invention discloses a polycarbazole-loaded nano-palladium material as well as a preparation method and application thereof. Specifically, the average grain diameter distribution of palladium nanoparticles prepared by the invention is about 4.2 nm and the palladium nanoparticles are uniformly dispersed on a substrate polycarbazole material. The material can be used for catalyzing Suzuki reaction of aryl bromide and aryl chloride under light illumination and water phase conditions, and has the characteristics of high conversion efficiency, wide applicable range, green and moderate reaction conditions and the like. After conversion reaction is finished, a substrate is separated from a reaction system and a catalysis system can be used for carrying out the next round of reaction; after thecatalysis system is circulated for 3 times, the catalysis system can still keep stable and the catalytic activity is not obviously reduced.

Description

technical field [0001] The invention belongs to the technical field of catalytic chemistry, and relates to a palladium nanomaterial supported by a carbazole polymer, a preparation method and an application thereof. Background technique [0002] Diaryl and polyaryl compounds have been widely used in the manufacture of medicines, chemical agricultural products, artificial substitutes for natural products, dyes and fragrances. At present, there are many main methods for the synthesis of such compounds, and the current research on the reaction of synthesizing such compounds is mainly focused on the use of homogeneous catalysts for heating reactions to overcome the driving force required for the catalytic cycle. There are many shortcomings in these catalytic systems, such as catalyst residue in the product, catalyst cannot be recycled, high temperature or electron sacrificial agent is required to promote the reaction, and it is easy to cause environmental pollution and so on. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01J31/06B01J37/16C07C45/68C07C49/784C07C49/84C07C49/86C07C47/546C07C253/30C07C255/56C07C255/50C07C201/12C07C205/45C07C205/06C07C67/343C07C69/76C07C41/30C07C43/205C07C209/68C07C211/48C07D333/54C07D213/16C07D215/06C07C1/32C07C15/14C07C15/24
CPCB01J31/069B01J37/16C07C1/321C07C41/30C07C45/68C07C67/343C07C201/12C07C209/68C07C253/30C07D213/16C07D215/06C07D333/54C07C49/784C07C49/84C07C49/86C07C47/546C07C255/56C07C255/50C07C205/45C07C205/06C07C69/76C07C43/205C07C211/48C07C15/14C07C15/24
Inventor 李红喜郭斌郎建平
Owner SUZHOU UNIV
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