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A ratiometric transition metal porphyrin polymer-based luminescent oxygen sensing material

A porphyrin polymer, transition metal technology, applied in luminescent materials, material excitation analysis, fluorescence/phosphorescence, etc., can solve problems such as inaccurate oxygen measurement

Active Publication Date: 2016-06-22
CHINA UNIV OF PETROLEUM (EAST CHINA)
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] In order to overcome the defect of inaccurate oxygen measurement caused by the loss of oxygen-sensing dyes, the object of the present invention is to provide a method for constructing a ratio-type transition metal porphyrin polymer-based luminescent oxygen sensing film, and apply it to luminescent oxygen Sensing field

Method used

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  • A ratiometric transition metal porphyrin polymer-based luminescent oxygen sensing material

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] 1: Synthesis of meso-5,10,15,20-tetrakis(4-cyanophenyl)porphyrin

[0025] Firstly, p-cyanobenzaldehyde (1.31g, 10mmol) was dissolved in 20mL of propionic acid, and freshly distilled pyrrole (0.737g, 11mmol, 0.76mL) was dissolved in 10mL of propionic acid. Then, under the protection of nitrogen, the propionic acid solution of pyrrole was slowly added dropwise to the propionic acid solution of p-cyanobenzaldehyde, heated to 80° C. for 1 h, cooled to room temperature, filtered, and the filter cake was washed with absolute ethanol. Purification by column chromatography with dichloromethane as the eluent gave a dark purple solid.

[0026] 2: Synthesis of meso-5,10,15,20-tetrakis(4-cyanophenyl)porphyrin platinum complex

[0027] PtCl 2 (37.0mg, 0.14mmol) was added to 35mL of benzonitrile, heated to reflux for 4h, and the PtCl 2 Add meso-5,10,15,20-tetrakis(4-cyanophenyl)porphyrin (32.8mg, 0.046mmol) after all dissolved in benzonitrile, and continue the reflux reaction for ...

Embodiment 2

[0031] 1: Synthesis of meso-5,10,15,20-tetrakis(4-cyanophenyl)porphyrin

[0032] Firstly, p-cyanobenzaldehyde (1.31g, 10mmol) was dissolved in 20mL of propionic acid, and freshly distilled pyrrole (0.737g, 11mmol, 0.76mL) was dissolved in 10mL of propionic acid. Then, under the protection of nitrogen, the propionic acid solution of pyrrole was slowly added dropwise to the propionic acid solution of p-cyanobenzaldehyde, heated to 80° C. for 1 h, cooled to room temperature, filtered, and the filter cake was washed with absolute ethanol. Purification by column chromatography with dichloromethane as the eluent gave a dark purple solid.

[0033] 2: Synthesis of meso-5,10,15,20-tetrakis(4-cyanophenyl)porphyrin iridium complex

[0034] IrCl 3 (41.7mg, 0.14mmol) was added to 35mL of benzonitrile, heated to reflux for 4h, and the IrCl 3 Add meso-5,10,15,20-tetrakis(4-cyanophenyl)porphyrin (32.8mg, 0.046mmol) after all dissolved in benzonitrile, and continue the reflux reaction for 2...

Embodiment 3

[0038] 1: Synthesis of meso-5,10,15,20-tetrakis(4-cyanophenyl)porphyrin

[0039] Firstly, p-cyanobenzaldehyde (1.31g, 10mmol) was dissolved in 20mL of propionic acid, and freshly distilled pyrrole (0.737g, 11mmol, 0.76mL) was dissolved in 10mL of propionic acid. Then, under the protection of nitrogen, the propionic acid solution of pyrrole was slowly added dropwise to the propionic acid solution of p-cyanobenzaldehyde, heated to 80° C. for 1 h, cooled to room temperature, filtered, and the filter cake was washed with absolute ethanol. Purification by column chromatography with dichloromethane as the eluent gave a dark purple solid.

[0040] 2: Synthesis of meso-5,10,15,20-tetrakis(4-cyanophenyl)porphyrin palladium complex

[0041] PdCl 2(24.8mg, 0.14mmol) was added to 35mL of benzonitrile, heated to reflux for 4h, and the PdCl 2 Add meso-5,10,15,20-tetrakis(4-cyanophenyl)porphyrin (32.8mg, 0.046mmol) after all dissolved in benzonitrile, and continue the reflux reaction for ...

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Abstract

The invention relates to a ratio-type transition metal porphyran polymer luminescent oxygen sensing material and a construction method thereof. BODIPY with strong luminous intensity is uniformly mixed with a transition metal porphyran complex in a certain ratio, BODIPY and the transition metal porphyran complex are stably connected together under the crosslinking action and then cover on a quartz sheet, so that the ratio-type transition metal porphyran polymer is constructed; BODIPY is not sensitive to oxygen while the transition metal porphyran complex is sensitive to oxygen, and determination of ratio-type oxygen sensing is realized by comparing the luminescent intensity ratio of BODIPY to the transition metal porphyran complex; besides, a transition metal complex with three different triple excited state lives is selected, and wide-range oxygen content can be accurately determined. The ratio-type transition metal porphyran polymer luminescent oxygen sensing material has the advantages that an oxygen sensing membrane is fixed in an optical fiber circulation tank and oxygen content can be accurately determined when being combined with a luminoscope.

Description

technical field [0001] The invention relates to a method for constructing a ratio-type luminescent oxygen sensing membrane. The ratio-type luminescence oxygen sensing membrane is prepared by using BODIPY and a transition metal porphyrin complex as raw materials through dissolution and mixing of raw materials, acid catalysis and polymerization. It can be applied to the measurement needs of different oxygen content, effectively reducing the measurement error caused by the loss of oxygen-transmitting dyes. Background technique [0002] Porphyrins are macrocyclic compounds containing four pyrrole molecules, including four nitrogen heteroatoms, and the carbon (5, 10, 15, 20 positions) between the four pyrrole rings is called the middle position carbon (meso position), and the remaining carbons that can be substituted on the pyrrole ring are called β-position carbons. Porphyrin has a coordination environment with a certain spatial position and coordination ability, so it can comp...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G73/00C09K11/06G01N21/64
Inventor 吴文婷吴雪岩吴明铂赵建章范维玉郑经堂李忠涛张金强李子澍战力英
Owner CHINA UNIV OF PETROLEUM (EAST CHINA)
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