Universal method for constructing chiral organic molecular cage

A molecular cage and universal technology, applied in the field of synthesis of chiral porous materials, can solve the problems of expensive reaction raw materials and difficulty in mass production, and achieve a wide range of ligands, simple and efficient ligand design, and reaction easy to scale up effect

Inactive Publication Date: 2020-11-10
YANCHENG INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] It can be seen from the search that there are many studies on the design of molecular cages. A. I. Cooper et al. (Cooper et al., Nature Chem. , 2017, 9, 17-25, DOI: 10.1038/NCHEM.2663) used tetraaldehyde ligands and cyclohexanediamine to self-assemble TCC series molecular cages in organic solvents, but the molecular cage ligands reported in this study The synthetic route involves a wide range of reaction types, some reaction raw materials are expensive, and the self-assembly solution system of molecular cages is mostly a

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  • Universal method for constructing chiral organic molecular cage
  • Universal method for constructing chiral organic molecular cage
  • Universal method for constructing chiral organic molecular cage

Examples

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Embodiment 1

[0032] Example 1 Synthesis of V-type pyridine[3+6]-type chiral molecular cage

[0033] The reaction formula is as follows:

[0034]

[0035] Synthesis of V-type pyridine tetraaldehyde

[0036] Weigh 3,5-dibromopyridine (4.68 g, 20 mmol), p-methoxyphenylboronic acid (6.68 g, 44 mmol), cesium carbonate (9.75 g, 30 mmol), tetrakis(triphenylphosphine) palladium (0.05g, 0.04 mmol), put into a 150ml two-necked bottle, add 80 ml of toluene, 20 ml of deionized water, reflux at 100°C under the protection of inert gas, react for 24 hours and cool to room temperature, a large number of transparent crystals precipitated in the solution, filtered and washed with water Compound 1 (4.2g, 72%) was obtained; 4.2 g of compound 1 and 20 g of pyridine hydrochloride were weighed into a 100 ml single-port reaction flask, refluxed at 190°C under nitrogen protection for 5 h, cooled to room temperature, and 80 ml of deionized After stirring water at room temperature for 0.5 h, a large amount of w...

Embodiment 2

[0039] Example 2 Synthesis of linear naphthyl [3+6] chiral molecular cage

[0040] The reaction formula is as follows:

[0041]

[0042] Synthesis of linear naphthyl tetraaldehyde:

[0043]Weigh 1,4-dibromonaphthalene (5.66 g, 20 mmol), p-methoxyphenylboronic acid (6.68 g, 44 mmol), cesium carbonate (9.75 g, 30 mmol), tetrakis(triphenylphosphine) Add palladium (0.05 g, 0.04 mmol) to a 150 ml two-necked bottle, add 80 ml of toluene, 20 ml of deionized water, reflux at 100 ° C under the protection of an inert gas, react for 24 h and cool to room temperature, a large number of white needle-like crystals precipitate in the solution, filter Wash with water to obtain compound 4 (6.10 g, 89%); weigh 6 g of compound 4 and 20 g of pyridine hydrochloride into a 100 ml single-port reaction flask, reflux at 190°C under nitrogen protection for 5 h, cool to room temperature, and add 80 ml to Ionized water was stirred at room temperature for 0.5 h, and a large amount of white powder was...

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Abstract

The invention discloses a universal method for constructing a chiral organic molecular cage, which comprises the following steps: with a 2,6-dicarbonyl-4-substituted phenol structure as a parent nucleus, carrying out aldehyde ligand synthesis by coupling reaction, methoxy protection and deprotection reaction, Duff reaction and the like; and then introducing polyaldehyde synthons with different structures and functions are constructed by introducing rigid functional groups such as various benzene rings, naphthalene and anthracene, and then efficiently constructing the chiral porous molecular cage by the polyaldehyde synthons and chiral cyclohexanediamine under organic/water/acid conditions. The method has the advantages of simple and efficient ligand design, rich chiral molecular cage configuration, easiness in purification, wide ligand application range, easiness in reaction expansion and the like. By utilizing the modular synthesis method, a series of chiral molecular cages with richand adjustable structures can be prepared on a large scale for the fields of adsorption, separation, catalysis, energy and the like.

Description

technical field [0001] The invention relates to the field of synthesis of chiral porous materials, in particular to a universal method for constructing chiral organic molecular cages. Background technique [0002] Chiral compounds play an important role in many fields such as life science, medicine, food science and material science. Chiral porous molecular cages are a new class of soluble porous materials developed in recent years. They have a shape-retainable rigid organic framework, permanent internal pores, and stacked through channels. At the same time, they have adjustable cavity sizes and are easy to post-modify. , Good solubility and so on. As a new class of chiral porous materials, the excellent solubility of chiral molecular cages endows them with advantages in processing, and also enables them to be combined with other materials to obtain more structures and properties. Chiral molecular cages have excellent application prospects in the fields of gas storage and ...

Claims

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Application Information

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IPC IPC(8): C07D471/22C07D487/22
CPCC07B2200/07C07D471/22C07D487/22
Inventor 张磊宋欣钰孙林谢杰吴俊姜瑞雨
Owner YANCHENG INST OF TECH
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