Terbium coordination compound singlet oxygen fluorescent probe and application thereof

A singlet oxygen and terbium complex technology, applied in the field of new terbium complex singlet oxygen fluorescent probes, to achieve high detection sensitivity, good selectivity, and high selectivity

Inactive Publication Date: 2006-08-02
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, singlet oxygen fluorescent probes based on rare earth complexes and their time-resolved fluorescence detection techniques have not been reported yet.

Method used

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  • Terbium coordination compound singlet oxygen fluorescent probe and application thereof
  • Terbium coordination compound singlet oxygen fluorescent probe and application thereof
  • Terbium coordination compound singlet oxygen fluorescent probe and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0031] Example 1. Ligand N, N, N 1 , N 1 -Synthesis of [2,6-bis(3'-aminomethyl-1'-pyrazolyl)-4-(9'-anthracenyl)pyridine]tetraacetic acid (PATA for short)

[0032] Ligand PATA synthetic route such as figure 1 As shown, the specific operation process is as follows:

[0033] (1) Synthesis of 2,6-dibromo-4-(9'-anthracenyl)pyridine (compound 1)

[0034] Add 2.52 grams of 4-amino-2,6-dibromopyridine (10.0 mmol) and 2.14 grams of anthracene (12.0 mmol) to 150 ml of acetic acid and 50 ml of dichloromethane, and add 2.0 grams of nitrosyl isoamyl ester dropwise under stirring at 0°C ; After the reaction solution was stirred and reacted at room temperature for 48 hours, saturated Na was added 2 CO 3 The solution was neutralized, and then the product was extracted with 4×60ml of chloroform; after the chloroform solution was dried with anhydrous sodium sulfate, the solvent was evaporated under reduced pressure; the product was separated by silica gel column chromatography, and the pro...

Embodiment 2

[0045] Example 2.PATA-Tb 3+ Reaction of Complexes with Singlet Oxygen

[0046] Equimolar amounts of PATA and TbCl 3 Soluble in 0.1mol / L NaHCO 3 In aqueous solution, PATA-Tb can be obtained 3+ The solution of the complex; using Na 2 MoO 4 Catalyzes H under weakly basic conditions 2 o 2 The generated singlet oxygen was used as the singlet oxygen source, and the PATA-Tb 3+ The reaction product of a complex with singlet oxygen. Specifically, add PATA-Tb to a 0.1mol / L carbonic acid buffer solution with a pH value of 10.5 3+ Complexes, Na 2 MoO 4 and a certain amount of H 2 o 2 , and the reaction solution was measured after reacting at 25° C. for 20 hours. figure 2 for PATA-Tb 3+ The mass spectrometry (ESI-MS) measurement results of the product after reacting with singlet oxygen show that the product is PATA-Tb 3+ The inner oxide (referred to as EP-PATA-Tb 3+ ).

Embodiment 3

[0047] Embodiment 3.PATA and rare earth ion (Eu 3+ and Tb 3+ ) Fluorescence property determination of complexes

[0048] 1. Fluorescence spectrum, fluorescence intensity and fluorescence lifetime

[0049] When PATA is mixed with rare earth ions in aqueous solution, it can rapidly form a stable and almost non-fluorescent complex. However, when it reacts with singlet oxygen, the fluorescence signal is significantly enhanced. Determination of PATA-Tb using 0.05mol / L boric acid buffer solution with pH value of 9.1 as solvent 3+ 、PATA-Eu 3+ and its inner oxide EP-PATA-Tb 3+ 、EP-PATA-Eu 3+ The UV-visible spectrum, fluorescence spectrum, molar absorptivity, fluorescence quantum yield and fluorescence lifetime in the solvent; the UV-visible spectrum was measured with a Tianmei UV 7500 spectrophotometer; the fluorescence was measured with a Perkin Elmer LS 50B fluorescence spectrophotometer. The quantum yield was measured using the complexes of 4'-phenyl-2,2':6',2"-biteropyridine-6...

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Abstract

The present invention relates to a determination technique of singlet oxygen (1O2) in solution, in the concrete, it relates to a new type terbium coordination compound singlet oxygen fluorescent probe and its application. Said coordination compound is formed by using trivalent terbium ion Tb3+ and ligand containing anthracene and its derivative substituted 2,6-dipyrazolylpyridine skeleton structure, which can be reacted with singlet oxygen molecule characteristics. Besides, said invention also provides the structure formula of said ligand. Said invention has good selectivity for singlet oxygen molecule, and can be used for quantitatively detecting singlet oxygen.

Description

technical field [0001] The present invention relates to singlet oxygen ( 1 o 2 ) measurement technology, specifically a novel terbium complex singlet oxygen fluorescent probe and its application. Background technique [0002] singlet oxygen ( 1 o 2 ) is an unstable form of oxygen molecules in a high-energy excited state. It exists widely in nature and plays an important role in many photochemical and photobiological reaction processes, such as photodegradation, phototransformation of pollutants, chemiluminescence, oxidative aging of organisms, and even photocarcinogenesis. There have been many reports on the application of singlet oxygen in organic synthesis, but its physiological oxidation in biological systems has attracted more and more attention from researchers. It implies a major impact on organisms and life systems. Various Biomolecules, including membrane lipids, proteins, amino acids, nucleotides, carbohydrates and thiols, can be oxidized by strongly oxidizing ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): G01N33/52G01N21/76C09K11/06C07F5/00C07D213/36
Inventor 袁景利谭明乾王桂兰
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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