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Metal organic complex containing benzimidazole skeleton as well as preparation method and application of metal organic complex

A metal-organic and benzimidazole technology is applied in the field of metal-organic complexes containing benzimidazole skeletons and the preparation thereof, and can solve the problems that the research is limited to the synthesis stage and the technology has not been further studied.

Active Publication Date: 2022-03-22
WUHAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008]However, the research on this type of compound is limited to the synthesis stage, and the existing technology has not carried out further research on the further development of its practical application value

Method used

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  • Metal organic complex containing benzimidazole skeleton as well as preparation method and application of metal organic complex
  • Metal organic complex containing benzimidazole skeleton as well as preparation method and application of metal organic complex
  • Metal organic complex containing benzimidazole skeleton as well as preparation method and application of metal organic complex

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preparation example Construction

[0054] The invention provides a method for preparing the above-mentioned organometallic complex containing a benzimidazole skeleton, comprising the following steps:

[0055] The organic ligand having the structure shown in formula I, the transition metal compound and the organic solvent are mixed and reacted to obtain a metal-organic complex containing a benzimidazole skeleton.

[0056] In the present invention, the preparation method of the organic ligand having the structure shown in formula I preferably comprises the following steps:

[0057] Under the action of a catalyst and a base, the benzimidazole compound having the structure shown in formula A and the amino compound having the structure shown in formula B undergo carbon-nitrogen coupling reaction to obtain the organic ligand having the structure shown in formula I.

[0058] R 3 -NH 2 Formula B;

[0059] In Formula A and Formula B, R 1 is hydrogen, methyl or chlorine;

[0060] R 2 It is C1~C3 alkyl;

[0061] ...

Embodiment 1

[0073] The organic ligand and the transition metal compound were dissolved in methanol respectively, and then the methanol solution of the transition metal compound was added to the refluxing methanol solution of the organic ligand, and the mixed solution was continued to reflux for 4 hours, then cooled to room temperature, and the blue solid precipitate was filtered out That is the crude product. The crude product was added into DMF (dissolved completely), and then slowly diffused into the DMF solution by diethyl ether to obtain the corresponding single crystal pure product. This method yields Co-1 and Co-2.

[0074] The preparation process of Co-1 is shown in formula (1), and the preparation process of Co-2 is shown in formula (2).

[0075]

[0076] Among them, the single crystal structure of Co-1 is shown in figure 1 Shown; the single crystal structure of Co-2 is shown in figure 2 shown.

Embodiment 2

[0078] The ratio of the organic ligand to the transition metal compound is 2:1, dissolved in methanol, then the mixed solution is refluxed for 4 hours and then cooled to room temperature, the yellow solid precipitated by filtration is the crude product, and then the mixed solvent of diethyl ether and ethyl acetate Pure product was obtained after rinsing 3 times. This method yields Ir-1 and Ir-2.

[0079] The preparation process of Ir-1 is shown in formula (3), and the preparation process of Ir-2 is shown in formula (4).

[0080]

[0081] Among them, the nuclear magnetic data of Ir-1 is:

[0082] 1 H NMR (500MHz, DMSO-d 6 )δ7.86(d, J=8.3Hz, 2H), 7.66(d, J=8.3Hz, 2H), 7.53(t, J=7.6Hz, 2H), 7.47(t, J=7.7Hz, 4H) ,7.24(t,J=7.4Hz,1H),7.03(d,J=7.8Hz,2H),4.01(s,6H),1.39(s,15H). 13 C NMR (126MHz, DMSO-d 6 )δ145.1, 142.3, 137.1, 134.4, 131.3, 125.3, 124.7, 124.4, 119.5, 114.6, 113.2, 88.0, 32.4, 9.2.

[0083] The nuclear magnetic data of Ir-2 is:

[0084] 1 H NMR (500MHz, DM...

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Abstract

The invention provides a metal organic complex containing a benzimidazole skeleton as well as a preparation method and application of the metal organic complex, and belongs to the technical field of metal organic chemistry and catalysis. The N atom of benzimidazole contains lone pair electrons, has strong coordination ability, can easily form a complex with transition metal, and has diversified coordination configurations. In addition, the complex has a good rigid plane structure, abundant pi electrons and an excellent electron delocalization environment, and the stability of the complex is higher due to the pi-pi accumulation effect of aromatic rings on benzimidazole. According to the invention, an organic compound containing a benzimidazole skeleton and having a structure as shown in a formula I is used as an organic ligand to react with a transition metal compound to obtain the metal organic complex having a structure as shown in a formula II-VI, and the obtained complex can be used as a catalyst to catalyze a reaction for preparing benzoic acid through alcohol dehydrogenation and has good catalytic activity.

Description

technical field [0001] The invention relates to the technical field of metal-organic chemistry and catalysis, in particular to a metal-organic complex containing a benzimidazole skeleton and a preparation method and application thereof. Background technique [0002] Benzimidazole and its derivatives are an important class of nitrogen heterocyclic compounds, which show unique properties in the fields of dyes, polymers, metal ligands, medicine and materials. In view of its unique properties and wide application prospects, molecules containing benzimidazole skeletons have attracted more and more attention from researchers in recent years. [0003] Currently, Chen Cheng’s team has successfully synthesized a class of organic compounds containing a benzimidazole skeleton with the structure shown in Formula I (Chem.Asian J.2020,15,129-135): [0004] [0005] In formula I, R 1 is hydrogen, methyl or chlorine; [0006] R 2 is methyl, ethyl or isopropyl; [0007] R 3 For phen...

Claims

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Application Information

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IPC IPC(8): C07F15/06C07F15/00C07F1/08C07F3/06B01J31/18B01J31/22C07C51/295C07C63/06
CPCC07F15/065C07F15/0033C07F15/0046C07F1/005C07F3/003B01J31/1835B01J31/2295C07C51/295C07B2200/13B01J2531/845B01J2531/821B01J2531/827B01J2531/16B01J2531/26B01J2531/0225B01J2531/0241C07C63/06Y02P20/584
Inventor 陈宬桑微沙南樊广高江博文陈原新江民
Owner WUHAN UNIV OF TECH
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