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A dye/metal-organic framework composite material with fluorescence upconversion performance and its preparation method and bioimaging application

A technology of organic frameworks and composite materials, applied in luminescent/biological dyeing preparations, luminescent materials, chemical instruments and methods, etc., can solve the problems of fluorescence quenching, poor solubility and biocompatibility limitations, etc.

Active Publication Date: 2021-06-04
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0002] Fluorescent dyes have been used in biological imaging, fluorescent probes, cell staining, and lighting LEDs due to their variety, convenient structure design, stable luminescence, and wide spectral range; however, organic dye molecules aggregate fluorescence quenching, solubility, and biological Poor compatibility limits its application

Method used

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  • A dye/metal-organic framework composite material with fluorescence upconversion performance and its preparation method and bioimaging application
  • A dye/metal-organic framework composite material with fluorescence upconversion performance and its preparation method and bioimaging application
  • A dye/metal-organic framework composite material with fluorescence upconversion performance and its preparation method and bioimaging application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Using gadolinium nitrate and 4,4'-[[2-[[3-(4-carboxyphenoxy)-2,2-bis[(4-carboxyphenoxy)methyl]propoxy]methyl] -2-[(4-carboxyphenoxy)methyl]-1,3-propanediol]bis(oxy)]bisbenzoic acid, synthesize metal-organic framework materials by solvothermal method, and its specific synthetic route is as follows:

[0032] Add 0.1 mmol of gadolinium nitrate and 0.1 mmol of 4,4'-[[2-[[3-(4-carboxyphenoxy)-2,2-bis[(4-carboxyphenoxy)methyl]propane Oxy]methyl]-2-[(4-carboxyphenoxy)methyl]-1,3-propanediol]bis(oxy)]bisbenzoic acid was dissolved in 7 mL DMF and 1 mL H 2 O mixed solvent, then add 1mL HNO 3 aqueous solution (1M). The solution was packaged in a 20mL polytetrafluoroethylene reactor and placed in an oven at 160°C for 72 hours. Cooled to room temperature, washed 3 times with DMF to obtain colorless needle-like metal-organic framework material Gd 2 L(DMF) 2 ·(H 2 O) 5 (DMF) 3 (abbreviated as Gd-HCOO). Put 40mg of this crystal into 0.001mol L -1A deionized water solution of ...

Embodiment 2

[0037] Using gadolinium nitrate and 4,4'-[[2-[[3-(4-carboxyphenoxy)-2,2-bis[(4-carboxyphenoxy)methyl]propoxy]methyl] -2-[(4-carboxyphenoxy)methyl]-1,3-propanediol]bis(oxy)]bisbenzoic acid, synthesize metal-organic framework materials by solvothermal method, and its specific synthetic route is as follows:

[0038] Add 0.1 mmol of gadolinium nitrate and 0.1 mmol of 4,4'-[[2-[[3-(4-carboxyphenoxy)-2,2-bis[(4-carboxyphenoxy)methyl]propane Oxy]methyl]-2-[(4-carboxyphenoxy)methyl]-1,3-propanediol]bis(oxy)]bisbenzoic acid was dissolved in 7 mL DMF and 1 mL H 2 O mixed solvent, then add 1mL HNO 3 aqueous solution (1M). The solution was packaged in a 20mL polytetrafluoroethylene reactor, and placed in an oven at 160°C for 72 hours. Cooled to room temperature, washed 3 times with DMF to obtain colorless needle-like metal-organic framework material Gd 2 L(DMF) 2 ·(H 2 O) 5 (DMF) 3 (Gd-HCOO). Put 40mg of this crystal into 0.001molL -1 Quinacridone (Qu) in deionized water. Put t...

Embodiment 3

[0041] Using gadolinium nitrate and 4,4'-[[2-[[3-(4-carboxyphenoxy)-2,2-bis[(4-carboxyphenoxy)methyl]propoxy]methyl] -2-[(4-carboxyphenoxy)methyl]-1,3-propanediol]bis(oxy)]bisbenzoic acid, synthesize metal-organic framework materials by solvothermal method, and its specific synthetic route is as follows:

[0042] Add 0.1 mmol of gadolinium nitrate and 0.1 mmol of 4,4'-[[2-[[3-(4-carboxyphenoxy)-2,2-bis[(4-carboxyphenoxy)methyl]propane Oxy]methyl]-2-[(4-carboxyphenoxy)methyl]-1,3-propanediol]bis(oxy)]bisbenzoic acid was dissolved in 7 mL DMF and 1 mL H 2 O mixed solvent, then add 1mL HNO 3 aqueous solution (1M). The solution was packaged in a 20mL polytetrafluoroethylene reactor, and placed in an oven at 160°C for 72 hours. Cooled to room temperature, washed 3 times with DMF to obtain colorless needle-like metal-organic framework material Gd 2 L(DMF) 2 ·(H 2 O) 5 (DMF) 3 (Gd-HCOO). Put 40mg of this crystal into 0.001molL -1 A deionized water solution of neutral red (N...

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Abstract

The invention discloses a dye / metal-organic framework composite material with fluorescence upconversion performance, its preparation method and biological imaging application. The chemical formula of the material is [M(L) x (G) y ]·(R) n , where M is a metal ion, L is a flexible organic ligand containing a hexacarboxylic acid group, G is a solvent molecule, and R is a dye molecule in the channel. The material is prepared by a solvothermal method. Under infrared / near-infrared light pumping, the frame can generate second-harmonic nonlinear optical signals, and then transfer energy to the dye, so that it can only emit light under ultraviolet-visible light pumping. dyes that can also emit light under infrared / near-infrared pumping. Utilizing the advantages of infrared / near-infrared light in the field of biological imaging reduces the limitation of excitation light; the loading of dyes on metal-organic framework materials also improves the biocompatibility of the dye itself and the problem of aggregation fluorescence quenching, broadening the field of The scope of application of dyes.

Description

technical field [0001] The invention relates to a dye / metal-organic framework composite material with fluorescence upconversion performance and a preparation method thereof. After the material is loaded with an organic dye, it can generate second harmonic nonlinearity under infrared / near-infrared light pumping The optical signal, and then the energy transfer to the dye, makes the dye that can only emit light under the pumping of ultraviolet and visible light, but also emits light under the infrared / near-infrared pumping, which expands the application range of the dye. Background technique [0002] Fluorescent dyes have been used in biological imaging, fluorescent probes, cell staining, and lighting LEDs due to their variety, convenient structure design, stable luminescence, and wide spectral range; however, organic dye molecules aggregate fluorescence quenching, solubility, and biological Poor compatibility limits its application. And most dyes can only be excited by ultrav...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G83/00C09K11/06A61K49/00
CPCA61K49/0021A61K49/0026A61K49/003A61K49/0052C08G83/008C09K11/06C09K2211/182
Inventor 崔元靖万雅婷钱国栋杨雨
Owner ZHEJIANG UNIV