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Relay-type multifunctional fluorescent probe, and preparation method and application thereof

A fluorescent probe, multifunctional technology, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., to achieve good sensitivity, excellent water solubility, and easy separation and purification of products

Inactive Publication Date: 2015-01-07
BOHAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although there have been a few fluorescent probe molecules with relay recognition function that can use one fluorescent probe molecule to realize continuous recognition of two ions under the same conditions, there are no fluorescent probes with relay recognition function that can recognize three ions. to report

Method used

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  • Relay-type multifunctional fluorescent probe, and preparation method and application thereof
  • Relay-type multifunctional fluorescent probe, and preparation method and application thereof
  • Relay-type multifunctional fluorescent probe, and preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0029] Example 1: Preparation of a relay-type multifunctional fluorescent probe

[0030] (1) The reaction formula of the synthetic relay type multifunctional fluorescent probe:

[0031]

[0032] (2) Concrete steps for synthesizing relay-type multifunctional fluorescent probes:

[0033] Weigh 0.400g of N,N'-((1,3,4-oxadiazol-2,5-yl)bis(2,1-phenyl))bis(2-chloroacetamide), 0.391g di -(Pyridylmethylene)amine, 1.5mL N,N-diisopropylethylamine and 0.104g potassium iodide, dissolved in 140mL dry acetonitrile, stirred and heated to reflux for 10h under the protection of nitrogen, wherein the heating and reflux temperature was 82°C The solvent is evaporated under reduced pressure at the end of the reaction, and the residue is separated by column chromatography with the eluent of ethyl acetate and methanol with a volume ratio of 10: 1 to obtain the relay type multifunctional fluorescent probe N, N'-(( 1,3,4-oxadiazol-2,5-yl)bis(2,1-phenyl))bis(2-(bis(pyridine-2-methylene)amino)aceta...

Embodiment 2

[0034] Example 2: Preparation of a relay-type multifunctional fluorescent probe

[0035] Weigh 0.400g of N,N'-((1,3,4-oxadiazol-2,5-yl)bis(2,1-phenyl))bis(2-chloroacetamide), 0.391g di -(pyridylmethylene)amine, 1.8mL of N,N-diisopropylethylamine and 0.104g of potassium iodide, dissolved in 140mL of dry acetonitrile, stirred and heated to reflux for 6h under the protection of nitrogen, wherein the temperature of heating to reflux was 82°C The solvent is evaporated under reduced pressure at the end of the reaction, and the residue is separated by column chromatography with the eluent of ethyl acetate and methanol with a volume ratio of 10: 1 to obtain the relay type multifunctional fluorescent probe N, N'-(( 1,3,4-oxadiazol-2,5-yl)bis(2,1-phenyl))bis(2-(bis(pyridine-2-methylene)amino)acetamide), the yield is 65%.

Embodiment 3

[0036] Example 3: Preparation of a relay-type multifunctional fluorescent probe

[0037] Weigh 0.400g of N,N'-((1,3,4-oxadiazol-2,5-yl)bis(2,1-phenyl))bis(2-chloroacetamide), 0.391g di -(Pyridylmethylene)amine, 1.8mL N,N-diisopropylethylamine and 0.104g potassium iodide, dissolved in 140mL dry acetonitrile, stirred and heated to reflux for 10h under the protection of nitrogen, wherein the heating and reflux temperature was 82°C The solvent is evaporated under reduced pressure at the end of the reaction, and the residue is separated by column chromatography with the eluent of ethyl acetate and methanol with a volume ratio of 10: 1 to obtain the relay type multifunctional fluorescent probe N, N'-(( 1,3,4-oxadiazol-2,5-yl)bis(2,1-phenyl))bis(2-(bis(pyridine-2-methylene)amino)acetamide), the yield is 72%.

[0038] The basic data of the relay-type multifunctional fluorescent probe N-(2-(1H-benzimidazolyl)phenyl)-2-bis(2-pyridylmethylamino)acetamide prepared in Examples 1 to 3 are...

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Abstract

The invention discloses a relay-type multifunctional fluorescent probe, and a preparation method and application thereof, belonging to the field of functional materials. The preparation method comprises the following steps: adding N-[2-(5-phenyl-1,3,4-oxadiazolyl-2-yl)phenyl]-2-chloroacetamide, di-(pyridylmethylene)amine, N,N-diisopropylethylamine and potassium iodide into acetonitrile, and stirring and heating under reflux in a nitrogen protective atmosphere; and after the reaction finishes, distilling under reduced pressure to remove the solvent, carrying out column chromatography separation on the residues to obtain the fluorescent probe N-[2-(5-phenyl-1,3,4-oxadiazolyl-2-yl)phenyl]-2-di(2-pyridylmethyleneamino)acetamide. The fluorescent probe has excellent water solubility, can be used for monitoring analysis and tracing of zinc ions, pyrophosphate and sulfur ions in a water environment system, and has favorable determination sensitivity for target ions.

Description

technical field [0001] The invention relates to the field of functional materials, in particular to a relay type multifunctional fluorescent probe, its preparation method and its application. Background technique [0002] Fluorescence recognition of metal ions and anions has become one of the very active research fields. Zinc ions, pyrophosphate (PPi) and sulfur ions (S 2- ) is of great significance in life sciences and environmental monitoring, and has received widespread attention in recent years. Currently, for the identification of zinc ions, pyrophosphate (PPi) and sulfur ions (S 2- ) fluorescent probes are mainly based on the fluorescence enhancement or quenching of the probe molecule at the same emission wavelength position, so this type of fluorescent probe is easily affected by external conditions such as probe concentration, excitation light wavelength and detection environment, which reduces the determination the accuracy of the results. So far, there is no re...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D413/14G01N21/64
Inventor 汤立军钟克利侯淑华彭亚晶郑竹轩
Owner BOHAI UNIV
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