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Indole ring substituted aminophenoxy zinc complex as well as preparation method and application thereof

A technology of aminophenoloxyzinc and indole ring, applied in the direction of zinc organic compounds and the like, can solve the problems of reduced catalytic activity and the like, and achieve the effects of high catalytic activity, convenient preparation and stable properties

Active Publication Date: 2021-04-09
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, although individual zinc complexes show high isotactic selectivity for the ring-opening polymerization of racemic lactide, their catalytic activity is much lower than that of general non-stereoselective zinc complexes.

Method used

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  • Indole ring substituted aminophenoxy zinc complex as well as preparation method and application thereof
  • Indole ring substituted aminophenoxy zinc complex as well as preparation method and application thereof
  • Indole ring substituted aminophenoxy zinc complex as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Synthesis of raw materials and intermediates:

[0046] (1) Synthesis of 2-indolecarboxamide (AN)

[0047]

[0048] Under argon protection, add 150 mL of dry CH to a 250 mL three-neck flask 2 Cl 2 , 2-indolecarboxylic acid (30mmol, 4.8g) was added and stirring was started. Then add SOCl 2 (60.0mmol, 8.57g), after heating to reflux for 2h, the solvent and excess thionyl chloride were evaporated with a rotary evaporator. Add 100mL CH 2 Cl 2 It was dissolved again, and the solvent was evaporated again with a rotary evaporator. After repeated three times, it was directly used in the next reaction.

[0049] Under argon protection, into a 250mL three-neck flask, add triethylamine (36mmol, 2.62g) and primary amine (36mmol) and 100mL dry CH 2 Cl 2 well mixed. Dissolve the 2-indolecarbonyl chloride obtained above in 50 mL of dry CH 2 Cl 2 , added dropwise to the reaction system. When preparing AN1 and AN2, a large amount of solids existed in the reaction flask afte...

Embodiment 2

[0062] Synthesis of Ligand L1

[0063] At room temperature, secondary amine N1 (3.64g, 14.2mmol), potassium carbonate (2.35g, 17.0mmol) and 40mL N,N-dimethylformamide were added to a 100mL single-necked bottle, stirred for 5min, and then added in 2 batches -Bromomethyl-4,6-dicumylphenol (5.99 g, 14.2 mmol). Continue to stir the reaction for 4h, TLC tracking shows that the reaction is complete, add 60mL water to quench, and use 30mL×3 CH 2 Cl 2 Extract, combine the organic phases, and wash with 60 mL×6 saturated brine. The organic phase was dried with anhydrous magnesium sulfate, filtered, and the filtrate was evaporated to remove the solvent with a rotary evaporator. Recrystallization from dichloromethane-petroleum ether system gave white solid product L1 (5.85 g, 41.2%).

[0064]

[0065] 1 H NMR (CDCl 3 ,400MHz,298K):δ10.06(br s,1H,OH),7.53(d, 3 J=7.8Hz, 1H, Indolyl-H), 7.33-7.11(m, 13H, 10H of ArH and 3H of Indolyl-H), 7.08(t, 3 J=7.0Hz, 1H, Indolyl-H), 6.78(d, 1...

Embodiment 3

[0067] Synthesis of Ligand L2

[0068] Reaction products were secondary amine N1 (2.69g, 10.5mmol), potassium carbonate (1.74g, 12.60mmol) and 2-bromomethyl-4-methyl-6-tritylphenol (4.65g, 10.5mmol) In addition, other operations were consistent with the synthesis of L1, and recrystallized from dichloromethane-petroleum ether system to obtain white solid L2 (3.93 g, 60.5%).

[0069]

[0070] 1 H NMR (CDCl 3 ,400MHz,298K):δ10.38(br s,1H,OH),7.53(d, 3 J=7.7Hz, 1H, Indolyl-H), 7.25-7.05(m, 18H, 15H of ArH and 3H of Indolyl-H), 6.88(d, 1H, 4 J=1.6Hz, ArH), 6.76(d, 1H, 4 J=1.6Hz, ArH), 6.22(s, 1H, Indolyl-H), 3.84-3.77(s, 2H, ArCH 2 N; q, 3 J=7.0Hz, 2H, NCH 2 CH 3 ),3.68(s,2H,Indolyl-CH 2 N),2.47(pesudo t,1H, 3 J=7.0Hz, NCH), 2.16(s, 3H, ArCH 3 ),1.80-1.65(m,4H,CH 2 of cyclohexyl),1.63-1.49(m,2H,CH 2 of cyclohexyl),1.37-1.23(m,2H,CH 2 of cyclohexyl),1.02-1.15(m,5H,2H ofcyclohexyl and 3H of NCH 2 CH 3 ). 13 C{ 1 H}NMR (CDCl 3 , 100MHz, 298K): δ154.2, 146.2, 13...

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Abstract

The invention discloses an indole ring substituted aminophenoxy zinc complex, a preparation method thereof and application of the indole ring substituted aminophenoxy zinc complex in catalyzing lactone ring-opening polymerization. The preparation method comprises the steps of directly reacting a neutral ligand with a metal raw material compound in an organic medium, filtering, concentrating, and recrystallizing to obtain the target compound. The indole ring substituted aminophenoxy zinc complex disclosed by the invention is an efficient lactone ring opening polymerization catalyst and can be used for catalyzing polymerization reaction of lactide and other lactones; and the method has a good effect on ring-opening polymerization of racemic lactide. The indole ring substituted aminophenoxy zinc complex has very obvious advantages that the raw materials are easy to obtain, the synthesis route is simple, the product yield is high, the catalytic activity and the three-dimensional adjustability are better, a high-impurity-specification and high-molecular-weight polyester material can be obtained under general conditions, and isotactic selectivity can be achieved by adding small organic molecules with an auxiliary coordination effect. The structural formula is shown in the description.

Description

technical field [0001] The invention relates to a class of indole ring substituted aminophenol oxyzinc complexes and the application of such complexes in lactone polymerization. Background technique [0002] The development of high molecular polymer materials has been filled with all aspects of human life. These materials are mainly petroleum-based polymer materials that are difficult to degrade. The extensive use of petroleum-based polymer materials is associated with two major social and economic problems: energy crisis and white pollution. Therefore, the development of polymer materials with sustainable properties to gradually replace these difficult-to-degrade petroleum-based materials has become a current research hotspot. [0003] Polylactic acid (also known as polylactide, PLA) is a renewable, degradable and biocompatible thermoplastic aliphatic polyester material derived from plant resources. And because of its similar physical and mechanical properties to some po...

Claims

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Application Information

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IPC IPC(8): C07F3/06C08G63/83C08G63/08
CPCC07F3/06C08G63/823C08G63/83C08G63/08
Inventor 马海燕索艳平
Owner EAST CHINA UNIV OF SCI & TECH
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