Dual-core metal organic complex with asymmetric structure and preparation and applications thereof

An organic complex, binuclear metal technology, applied in structural asymmetric binuclear metal-organic complex and its preparation, metal-organic complex, metal-organic complex as a catalyst in the application field, can solve problems such as complex synthesis, achieve high reaction Active, extended industrial application range, wide-ranging effects

Active Publication Date: 2019-08-20
TAIYUAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, currently reported binuclear metal-organic complexes are all symmetrical in structure. Due to the complexity of synthesis, structurally asymmetric binuclear metal-organic complexes and catalytic polymerization of cyclic esters have not been reported.

Method used

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  • Dual-core metal organic complex with asymmetric structure and preparation and applications thereof
  • Dual-core metal organic complex with asymmetric structure and preparation and applications thereof
  • Dual-core metal organic complex with asymmetric structure and preparation and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] The specific reaction process of the metal organic complex I-1 is represented by the following reaction equation.

[0053]

[0054] In the absence of water and oxygen, 0.05mol 2,2'-dihydroxy-[1,1'-diphenyl]-3-carbaldehyde (synthesized by the method of document Organometallics, 2007, 26, 2609‒2615), 0.075mol Polyoxymethylene and 0.05mol morpholine were dissolved in toluene, heated to reflux for 5h. Extract with ethyl acetate, wash with sodium chloride solution, dry over sodium sulfate, and evaporate the solvent by rotary evaporation. The obtained solid was dissolved in a mixed solvent of ethyl acetate and petroleum ether, the target compound solution was separated by a chromatographic column, and the solvent was rotary evaporated to obtain a white solid 2,2'-dihydroxy-3'-(morpholine-4- Base)-[1,1'-diphenyl]-3-carbaldehyde 10.5g, yield 67%.

[0055] In the absence of water and oxygen, mix 0.02mol 2,2'-dihydroxy-3'-(morpholin-4-yl)-[1,1'-diphenyl]-3-carbaldehyde with ...

Embodiment 2

[0062] The specific reaction process of the metal organic complex I-2 is represented by the following reaction equation.

[0063]

[0064] In the absence of water and oxygen, dissolve 0.05mol 2,2'-dihydroxy-[1,1'-diphenyl]-3-carbaldehyde, 0.075mol polyoxymethylene and 0.05mol pyrrolidine in toluene, and heat to reflux for reaction 7h. Extract with ethyl acetate, wash with sodium chloride solution, dry over sodium sulfate, and evaporate the solvent by rotary evaporation. The obtained solid was dissolved in a mixed solvent of ethyl acetate and petroleum ether, the solution of the target compound was separated by a chromatographic column, and the solvent was rotary evaporated to obtain a white solid 2,2'-dihydroxy-3'-(pyrrolidine-4- Base)-[1,1'-diphenyl]-3-carbaldehyde 9.3g, yield 63%.

[0065] In the absence of water and oxygen, 0.03mol 2,2'-dihydroxy-3'-(pyrrolidin-4-yl)-[1,1'-diphenyl]-3-carbaldehyde and 0.03mol 1-benzyl Basepiperidin-4-amine was heated under reflux in m...

Embodiment 3

[0070] The specific reaction process of the metal organic complex I-3 is represented by the following reaction equation.

[0071]

[0072] In the absence of water and oxygen, take 0.004mol of the ligand L1 prepared in Example 1 and dissolve it in 20ml of toluene, and slowly add 0.008mol of the metal alkyl compound In(CH 2 SiMe 3 ) 3 The toluene solution was heated to 100°C for 5 h, and the reaction solvent was removed under vacuum to obtain 3.8 g of metal organic complex I-3 light yellow powder with a yield of 89%.

[0073] 1 H-NMR (298 K, CD 2 Cl 2 , 400 MHz): δ 8.31 (d, J = 4.4 Hz, 1H,C H N), 7.61(dd, J = 7.4, 1.8 Hz, 1H, Ar- H ), 7.47 – 7.32 (m, 7H, Ar- H ), 7.26 (dd, J =7.4, 1.7 Hz, 1H, Ar- H ), 6.86 (t, J = 7.6 Hz, 1H, Ar- H ), 6.79 (t, J = 7.5 Hz,1H, Ar- H ), 3.98 (s, 2H, ArC H 2 N), 3.89 (d, J = 18.6 Hz, 4H, morpholin-C H 2 ),3.57 (s, 2H, ArC H 2 N pip), 3.50 – 3.43 (m, 1H, C H pip), 3.21 (s, 2H, morpholin-C H 2 ), 3.08 – 3.00 (m, 2...

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Abstract

The invention discloses a dual-core metal organic complex with an asymmetric structure, which is represented by the formula (I). The organic complex can be used as a catalyst for ring-opening polymerization of cyclic esters and is applied to ring-opening polymerization of different cyclic esters. Due to the cooperation between dual metals, only a small amount of the metal organic complex can catalyze the ring-opening polymerization of cyclic esters efficiently, and the catalysis efficiency and catalytic activity are high. Due to the asymmetric structure of the catalyst, the stereo-selectivityof the polymerization reactions can be adjusted in a greater range; corresponding polymers have abundant structural characteristics and multiple physical and chemical properties; and the application range is enlarged.

Description

technical field [0001] The invention belongs to the technical field of catalysts, and relates to a metal-organic complex, in particular to a structurally asymmetric binuclear metal-organic complex and its preparation, as well as the application of the metal-organic complex as a catalyst. Background technique [0002] The rapid development of petroleum-based synthetic polymer materials has brought great convenience to human life. However, the degradation time of petroleum-based plastic particles is very long, which takes about 500 to 1000 years. A large number of discarded plastic products have caused serious environmental pollution and also caused serious harm to the human body. [0003] In order to change this phenomenon, researchers are committed to finding renewable polymers to replace petroleum-based plastic products, which can effectively reduce the harm of plastic products to the environment and human health, and fundamentally solve the "white pollution" problem. [...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/06C07F5/00C08G63/84C08G63/08
CPCC07F5/00C07F5/066C08G63/08C08G63/823
Inventor 王兴宝范欢欢张萌
Owner TAIYUAN UNIV OF TECH
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