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Calixarene aza-crown ether derivative, its preparation and use as metal ion fluorescent identification agent

An azacrown ether and calixarene technology, which is applied in the field of new compounds and can solve the problems of long waiting time and troublesome handling.

Inactive Publication Date: 2007-06-20
BEIJING NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although these two methods are intuitive and easy to understand, they take a long time to wait and are troublesome to deal with.

Method used

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  • Calixarene aza-crown ether derivative, its preparation and use as metal ion fluorescent identification agent
  • Calixarene aza-crown ether derivative, its preparation and use as metal ion fluorescent identification agent
  • Calixarene aza-crown ether derivative, its preparation and use as metal ion fluorescent identification agent

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Preparation of 25,27-bis(3-bromopropoxy)-26,28-dihydroxy-5,11,17,23-tetra-tert-butylcalix[4]arene

[0028] In a container equipped with a reflux condenser, inject acetonitrile (250 ml) dried over anhydrous magnesium sulfate for 24 hours, then add p-tert-butylcalix [4] arene (6.46 g, 10 mmol), 1,3- Dibromopropane (10.2 mL, 100 mmol) and anhydrous potassium carbonate (3.45 g, 25 mmol). Heated and stirred to reflux for 48 hours, cooled, and the solvent acetonitrile was evaporated to dryness under reduced pressure. Chloroform (200 ml) was added to the obtained solid, and washed with 5% hydrochloric acid, saturated aqueous sodium bicarbonate solution, and distilled water, each washing three times, using 100 ml each time. Add 10 g of anhydrous sodium sulfate to chloroform and dry for 24 hours. The desiccant magnesium sulfate was filtered off, and the solvent chloroform was rotary evaporated under reduced pressure to obtain a white solid (slightly yellowish) crude product....

Embodiment 2

[0030] Preparation of Serine Ethyl Ester Hydrochloride

[0031]Add redistilled absolute ethanol (100 ml) into a three-necked flask equipped with a condenser, an exhaust gas absorption device, and an air inlet device. Dry hydrogen chloride was passed through for 1 hour, so that absolute ethanol was saturated with respect to hydrogen chloride. Then cool in an ice bath, add 3.5 g of serine, and continue stirring with hydrogen chloride under the ice bath for 1 hour. The ice bath was removed, and heated to reflux for half an hour. After cooling, add 10 g of anhydrous magnesium sulfate and dry for 24 hours. The desiccant was filtered off, half of the solvent was evaporated, and the product was left standing overnight in the refrigerator, and colorless crystals were precipitated, filtered, and vacuum-dried to obtain a colorless crystalline product. Melting point: 160-160.8°C, literature value 159-162°C. IR (KBr, ν, cm -1 ): 3384.3, 2975.0, 1978.6, 1746.6, 1583.1. These values...

Embodiment 3

[0033] Preparation of compounds of the present invention

[0034] In a container equipped with a reflux condenser, inject acetonitrile (200 ml) dried over anhydrous magnesium sulfate for 24 hours, and then add 25,27-bis(3-bromopropoxy)-26,28-dihydroxy-5 , 11,17,23-Tetra-tert-butylcalix[4]arene (Example 1, 2 g, 2.24 mmol), anhydrous potassium carbonate (4.03 g, 29.2 mmol). Serine ethyl ester hydrochloride 3.82 g (22.4 mmol), first add 1 / 3 of the amount, heat to reflux, then add 1 / 3 of the amount every 8 hours, and add the serine ethyl ester hydrochloride three times. After adding the last batch of serine ethyl ester hydrochloride, heat, stir and reflux for two days. After cooling, the solvent acetonitrile was evaporated to dryness under reduced pressure. Chloroform (100 ml) was added to the obtained solid, and washed three times with dilute hydrochloric acid, saturated aqueous sodium bicarbonate solution and distilled water respectively. Add 10 g of anhydrous sodium sulfat...

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Abstract

A compound as metal ionic fluorescent identifying agent, its production and use are disclosed. The process is carried out by connecting calitetrarene with serine ethyl ester. It can be used to identify CO2+, Cu2, Ni2+, Fe3+, Ru3+ and Ag+ and used as Fe3+ fluorescent probe.

Description

technical field [0001] The invention relates to a class of novel compounds which can be used as metal ion fluorescent recognition reagents, its preparation method and its application. More specifically, the present invention relates to calixarene azacrown ether derivatives, their preparation methods and their use as metal ion fluorescence recognition reagents. Background of the invention [0002] The concept of molecular recognition was originally used to study chemical problems in biological systems at the molecular level. With the emergence of the emerging discipline of modern supramolecular chemistry, molecular recognition has gradually become one of the core research contents of this discipline. Molecular recognition refers to the process in which the subject selectively binds to the object and produces a specific function. They do not rely on the traditional covalent bond force, but rely on the intermolecular force of non-covalent bond force. Molecular recognition ca...

Claims

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Application Information

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IPC IPC(8): C07D273/01G01N21/76
Inventor 延玺李加冕陈河平司书峰
Owner BEIJING NORMAL UNIVERSITY
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