Amino-functionalized water-soluble pillar[6]arene and preparation method thereof

An amino-functionalized and water-soluble technology, applied in the preparation of amino hydroxy compounds, chemical instruments and methods, preparation of organic compounds, etc., can solve the problems of low yield of target products, cumbersome synthesis methods, complicated operations, etc., and achieve the price of raw materials. Low cost, high product yield and simple operation

Inactive Publication Date: 2017-03-15
HENAN INST OF ENG
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  • Abstract
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Problems solved by technology

In 2011, Hou's research group first reported the synthesis of water-soluble pillar[5]arenes under acidic conditions, but this synthesis meth...

Method used

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  • Amino-functionalized water-soluble pillar[6]arene and preparation method thereof
  • Amino-functionalized water-soluble pillar[6]arene and preparation method thereof
  • Amino-functionalized water-soluble pillar[6]arene and preparation method thereof

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Embodiment 1

[0031] Amino-functionalized water-soluble pillar [6] arenes, the chemical structure of which is as follows:

[0032] .

[0033] In the present invention, g stands for "gram"; mmol stands for "millimole"; mol stands for "mole"; mL stands for "milliliter"; V / V stands for volume ratio; h stands for "hour".

[0034] The present invention also provides a method for preparing the above-mentioned amino-functionalized water-soluble pillar[6]arene, which is carried out according to the following steps:

[0035]

[0036](1) The first step is the preparation of compound (I), namely 1,4-bis(2-bromoethoxy)benzene: first, dihydroxyethyl ether of hydroquinone (10.0 g, 50 mmol), three Phenylphosphine (31.5 g, 120.0 mmol) and solvent acetonitrile (200 g, 250 mL) were added into a 500 mL three-neck flask, and then the reaction system was placed in an ice bath until the temperature of the reaction system was 0 °C, stirred evenly at 0 °C, and then Add carbon tetrabromide (39.8 g, 120.0 mmo...

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Abstract

The invention discloses an amino-functionalized water-soluble pillar[6]arene and a preparation method thereof. The preparation method for amino-functionalized water-soluble pillar[6]arene comprises the following steps: (1) preparing 1,4-bis(2-bromoethoxy)benzene (I) from hydroquinone dihydroxyethyl ether; (2) preparing bromo-functionalized pillararene (II) from 1,4-bis(2-bromoethoxy)benzene (I); (3) preparing azido-functionalized pillararene (III) from bromo-functionalized pillararene (II); and (4) preparing the amino-functionalized water-soluble pillar[6]arene with azido-functionalized pillararene (III) as a raw material. The amino-functionalized water-soluble pillar[6]arene prepared in the invention has a pillar framework which is composed of six benzene rings and six methylene groups and connected with twelve amino groups and contains a plurality of recognition sites; the amino-functionalized water-soluble pillar[6]arene has good dissolvability in both methanol and an aqueous acidic solution; and the preparation method has the advantages of mild reaction conditions, simple operation, high product yield, large molecular cavity and the like.

Description

technical field [0001] The invention relates to a pillar aromatic hydrocarbon compound, in particular to an amino-functionalized water-soluble pillar [6] aromatic hydrocarbon and a preparation method thereof. Background technique [0002] Pillararenes are a new class of macrocyclic host molecules after crown ethers, cyclodextrins, calixarenes and cucurbiturils. Since they were first reported by Ogohi’s research group in 2008, they have been known for their unique morphological structure and excellent host molecules. Object properties have received extensive attention. Pillararenes, which are formed by connecting the 2-position and 5-position of the benzene ring through methylene groups, have more structural symmetry and rigidity than calixarenes. Therefore, as a new generation of host molecules, pillararenes have unique advantages in the research of supramolecular chemistry. The advantages. [0003] However, the early research was limited to organic solvents, so the synthe...

Claims

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Application Information

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IPC IPC(8): C07C213/00C07C217/20C07C41/22C07C41/30C07C43/225C07C247/04C09K11/06G01N21/64
CPCC07C41/22C07C41/30C07C213/00C07C247/04C09K11/06C09K2211/1007G01N21/643C07C217/20C07C43/225
Inventor 段群鹏赵龙涛薛孟晓吕名秀王延伟廖肃然
Owner HENAN INST OF ENG
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