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Coordination compound LIFM-CL1 based on ESIPT (excited state intramolecular proton transfer) characteristics and preparation method and application thereof

A LIFM-CL1-H2O, complex technology, applied in the direction of zinc organic compounds, chemical instruments and methods, organic chemistry, etc., can solve the problems of difficult reuse, inability to realize detection, etc., achieve reversible water response, easy processing, beneficial to The effect of device application

Active Publication Date: 2016-07-20
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003]However, currently commonly used fluorescent water-responsive materials are limited to fluorescent organic molecules. Detection of medium and trace water (<1%v / v)

Method used

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  • Coordination compound LIFM-CL1 based on ESIPT (excited state intramolecular proton transfer) characteristics and preparation method and application thereof
  • Coordination compound LIFM-CL1 based on ESIPT (excited state intramolecular proton transfer) characteristics and preparation method and application thereof
  • Coordination compound LIFM-CL1 based on ESIPT (excited state intramolecular proton transfer) characteristics and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0100] Embodiment 1 Preparation of organic ligand H2hpi2cf

[0101] 1. The preparation method of the organic ligand H2hpi2cf is as follows:

[0102] S1. Under nitrogen protection, a mixed solution of 5-aminoisophthalic acid (5mmol, 0.905g), 5-fluoro-2-hydroxy-benzaldehyde (3mmol, 0.420g) and acetic acid (20mL) was heated at 110°C stir for two hours;

[0103] S2. Add 4,4'-difluorobenzil (5mmol, 1.23g) and aminoacetic acid (50mmol, 3.85g) to the solution of S1, and continue to stir for 10 hours under heating conditions; S3. Cool to room temperature, and The white solid was filtered, washed several times with water, and then dried at 100°C to obtain H 2 The hpi2cf molecule.

[0104] 2. The structural formula of the organic ligand H2hpi2cf is as attached figure 1 shown.

Embodiment 2

[0105] Preparation of Example 2 Complex LIFM-CL1

[0106] h 2 The molecular structure of hpi2cf and the preparation of complex LIFM-CL1 are shown in the attached figure 1 shown.

[0107] 1. Preparation of complex LIFM-CL1:

[0108] Zinc nitrate hexahydrate (0.1mmol, 0.030g), H 2 hpi2cf (0.1mmol, 0.053g) was put into a 10mL reaction kettle lined with polytetrafluoroethylene, then 2mL water and 2mL N,N-dimethylacetamide were added, stirred evenly, covered and put into a matching stainless steel reaction vessel kettle. Put the reaction kettle into an oven, program the temperature to rise to 100°C for 2 hours, maintain this temperature for 50 hours, and cool down to room temperature for 10 hours. The mixture was filtered to obtain a colorless and transparent complex single crystal (blue fluorescence at 463nm under excitation at 365nm).

[0109] Or: zinc nitrate hexahydrate (0.1mmol, 0.030g), H 2 Put hpi2cf (0.1mmol, 0.053g) into a 15mL pressure-resistant reaction tube, ad...

Embodiment 3

[0117] Example 3 Preparation of Fluorescent Water Responsive Film

[0118] Method 1: Fully grind the complex LIFM-CL1, take 0.020g powder and disperse it in 10mL methanol solvent, and evenly smear it on non-fluorescent paper (that is, any other type of paper that is not fluorescent paper, such as filter paper, non-fluorescent picture Paper, etc.) to obtain a fluorescent film with a paper substrate (463nm blue fluorescence under 365nm excitation), which is also recorded as fluorescent paper;

[0119] Method 2: Fully grind the complex LIFM-CL1, take 0.020g powder and disperse it in 10mL n-heptane solvent, add 0.2g RTV silicone rubber, ultrasonic for 10 minutes, put the mixture in a mold with a certain shape, and let it stand at room temperature. Set aside for about 3 hours to fully volatilize the solvent to obtain a transparent and flexible fluorescent film material (463nm blue fluorescence under 365nm excitation), which is also recorded as RTV fluorescent film.

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Abstract

The invention discloses organic ligand H2hpi2cf based on ESIPT (excited state intramolecular proton transfer) characteristics and a preparation method and application of its Zn2+ complex (complex LIFM-CL1). The organic ligand H2hpi2cf has a molecular formula: 5-(2-(5-fluoro-2-2-hydroxyphenyl)-4,5-bis(4-fluorophenyl)-1H-imidazole-1-yl) isophthalic acid; on this basis, the complex LIFM-CL1 and a fluorescent water responsive film under in-situ single crystal conversion based on this complex are prepared, and the organic ligand has a promising application prospect in terms of heat-sensitive fluorescence, vapor-in-gas detection or fluorescent detection of trace water in an organic solvent; the organic ligand has the advantages that super-fast reversible water response process can be achieved at room temperature, solvent loss in the organic solvent detection process due to detection material dissolution is never caused, and the detection material is recyclable; a prepared fluorescent probe film has good physical characteristics and light emission stability and is reusable many times for a long time.

Description

technical field [0001] The invention belongs to the technical field of water content detection in chemical production. More specifically, an organic ligand based on the excited-state intramolecular proton transfer (ESIPT) property of the organic ligand is denoted as H 2 hpi2cf and its Zn 2+ The preparation method and application of the complex (coordination compound LIFM-CL1). Background technique [0002] The detection of water content in gases and organic solvents is an important part of the chemical production process. Compared with traditional Karl Fischer titration and electrochemical sensors, fluorescent water molecule responsive materials have the advantages of simple operation, easy portability, in-situ detection, and simple synthesis. . [0003] However, currently commonly used fluorescent water-responsive materials are limited to fluorescent organic molecules, which are generally difficult to reuse, and often cannot detect trace amounts of water (<1% v / v) in ...

Claims

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Application Information

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IPC IPC(8): C07D233/64C07F3/06C09K11/06G01N21/64
CPCG01N21/643C09K11/06C07D233/64C07F3/06C09K2211/188
Inventor 潘梅苏成勇陈玲严诚王海平范雅楠韦张文
Owner SUN YAT SEN UNIV
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