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Preparation of 8-hydroxyquinoline functionalized column [5] arene as well as construction and application of organic framework

A hydroxyquinoline, organic framework technology, applied in the field of compound synthesis and ion detection, can solve problems such as few reports of detection methods

Inactive Publication Date: 2018-10-02
NORTHWEST NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Currently, most of the reported fluoride ion F - The detection method can only detect fluoride ion F in an organic solvent system or a mixed system containing a certain proportion of organic solvents - , there are few reports on detection methods that can be applied to pure water systems

Method used

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  • Preparation of 8-hydroxyquinoline functionalized column [5] arene as well as construction and application of organic framework
  • Preparation of 8-hydroxyquinoline functionalized column [5] arene as well as construction and application of organic framework
  • Preparation of 8-hydroxyquinoline functionalized column [5] arene as well as construction and application of organic framework

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] Embodiment 1, the synthesis of P5Q

[0054] (1) Synthesis of intermediate M: Add 4mmol (0.8560g) of 1,4-dibromobutane, 4mmol (0.6641g) of potassium iodide and 400mL of acetone to a 250mL round bottom flask, stir at room temperature for 30 minutes, then add Anhydrous potassium carbonate 1mmol (0.1381g) and hydroquinone 1mmol (0.1105g), immediately with N 2 protection, the mixture was heated and refluxed at 60°C for 72 hours, suction filtered while it was hot, mixed with silica gel, spin-dried, and purified by column chromatography (petroleum ether: ethyl acetate = 50:1v / v), the obtained white The product is M. Yield: 91%, melting point: 85~86°C.

[0055] (2) Synthesis of P5C4 with four carbon pillars [5] aromatics on both sides: 5mmol (1.8901g) of intermediate M, 20mmol (2.7652g) of 1,4-dimethoxybenzene, and paraformaldehyde were added to a 250ml round bottom flask. 25mmol (0.7503g) and 250mL of 1,2-dichloroethane, stirred at room temperature for 30min, then added bor...

Embodiment 2

[0058] Example 2. Construction of Supramolecular Organic Framework P5QG

[0059] Weigh 15 mg (1.3×10 -5 mol) P5Q, 14mg (1.3×10-5 mol) pillar[5]arene P5C6 with six carbons on both sides, add 0.2mL cyclohexanol solution, heat to dissolve, and cool to form a stable supramolecular organic framework P5QG. P5QG has a strong light blue aggregation-induced fluorescence. The minimum gel-forming concentration of the supramolecular organic framework is 10 mg / mL. The inversion temperature is 45~48℃.

[0060] P5C6 was synthesized by the literature method (T. Ogoshi, R. Sueto, K. Yoshikoshi, K. Yasuhara, and TA. Yamagishi. J. Am. Chem. Soc. 2016, 138, 8064-8067).

Embodiment 3

[0061] Example 3: Supramolecular organic framework P5QG recognizes Fe 3+

[0062] Take 16 parts of a small amount (about 0.01g) of supramolecular organic framework P5QG on the white dripping plate, and add Mg to these supramolecular organic framework P5QG respectively 2+ , Ca 2+ , Cr 3+ , Fe 3+ ,Co 2+ , Ni 2+ , Cu 2+ , Zn 2+ , Ag + , Cd 2+ , Hg 2+ , Pb 2+ , Ba 2+ , Al 3+ , La 3+ and Eu 3+ aqueous solution (1moL / L). Then the fluorescence color change of the supramolecular organic framework P5QG was observed under UV light. The fluorescence of the supramolecular organic framework P5QG is quenched, indicating that the addition of Fe 3+ solution; if the fluorescence of the supramolecular organic framework P5QG does not change, it means that the aqueous solution of other ions is added.

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Abstract

The invention discloses 8-hydroxyquinoline functionalized column [5] arene P5Q. The functionalized column [5] arene P5Q can be constructed into a supramolecular organic framework P5QG having light blue aggregative state induced fluorescence together with bilateral six-carbon column [5] arene P5C6 through intermolecular self-assembling and the pi-pi stacking action of a gelator P5Q. The supramolecular organic framework P5QG and Fe<3+> can construct a supermolecular metal organic framework P5QG-Fe through the cation-pi action, and the process breaks the pi-pi stacking action of the gelator P5Q,which leads to fluorescence quenching of the supramolecular organic framework P5QG. Therefore, the supramolecular organic framework P5QG can be used for detecting the ultrasensitiveness of Fe<3+> viafluorescence, and the lowest detection line is 1.02 x 10<-11>M; and the Fe<3+> can be also removed from the aqueous solution (the removal rate is up to 99.96 percent).

Description

technical field [0001] The present invention relates to a functionalized pillar [5] aromatic hydrocarbon, in particular to a kind of 8-hydroxyquinoline functionalized pillar [5] aromatic hydrocarbon; the present invention also relates to the supramolecular organic framework based on the functionalized pillar [5] aromatic hydrocarbon Construction; The present invention also relates to the supramolecular organic framework in ultrasensitive detection separation Fe 3+ and continuity identification F - The application of the invention belongs to the technical field of compound synthesis and the field of ion detection. Background technique [0002] Fe combines with proteins in various forms to form ferritin, cytochrome, peroxidase, leghemoglobin, and ferredoxin, which play a key role in many biochemical processes at the cellular level. The lack of iron in the human body will affect the synthesis of hemoglobin and myoglobin, and reduce the activity of certain enzymes, such as cyt...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/26C09K11/06C08G83/00G01N21/64
CPCC07D215/26C08G83/008C09K11/06C09K2211/1416C09K2211/1466G01N21/64G01N21/6428G01N21/643G01N2021/6417G01N2021/6432G01N2021/6443
Inventor 张有明何俊霞林奇朱伟李永福房虎姚虹魏太保
Owner NORTHWEST NORMAL UNIVERSITY
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