Singlet oxygen europium coordination compound fluorescent probe and application thereof

A technology of europium complexes and fluorescent probes, which is applied in the field of new 1O2 europium complex fluorescent probes, can solve the problems of poor water solubility and unfavorable measurement of probes, and achieve high sensitivity, good selectivity, and high stability.

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

This method has good selectivity, high sensitivity, and rapid detection, but the poor water solubility of the probe is not conducive to biological systems. 1 o 2 Determination of

Method used

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  • Singlet oxygen europium coordination compound fluorescent probe and application thereof
  • Singlet oxygen europium coordination compound fluorescent probe and application thereof
  • Singlet oxygen europium coordination compound fluorescent probe and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Example 1. Synthesis of ligand [4'-(9-anthracenyl)-2,2':6'2"-biteropyridine-6,6"-dimethylamine]tetraacetic acid (ATTA for short).

[0027] Synthetic route such as figure 2 As shown, the substrate operation process is as follows.

[0028] (1) Synthesis of (E)-3-(9-anthracenyl)-1-(2'-pyridyl)-2-propenone (compound 1)

[0029] 10.31 grams of 9-anthral (50mmol) and 2.81 grams of KOH (50mmol) were mixed and dissolved in a mixed solution composed of 200ml of methanol and 40ml of water; after stirring for 30 minutes, 6.06 grams of 2-acetylpyridine (50mmol) was slowly added dropwise to The reaction system was stirred at room temperature for 24 hours; the precipitate was collected by filtration, and the crude product was recrystallized from ethanol; 12.77 g of the target compound was obtained, with a yield of 82.6%. 1 H NMR (CDCl 3 ) measurement results: δ=8.48-8.54 (m, 5H); 7.92 (m, 1H); 8.03 (d, J=8.4Hz, 2H); 8.27-8.31 (m, 2H); 8.37 (d, J=8.0 Hz, 2H); 8.48 (s, 1H); 8.70 (d...

Embodiment 2

[0045] Example 2. 10-methyl-9-anthracenyl and 10-phenyl-9-anthracenyl substituted [2,2':6',2"-biterpyridine-6,6"-dimethylamine] tetra Synthesis of acetic acid ligand

[0046] Synthetic route such as image 3 Shown, synthetic operation method is identical with embodiment 1.

Embodiment 3

[0047] Example 3. Ligands ATTA and Eu 3+ complexes (abbreviated as ATTA-Eu 3+ )and 1 o 2 Reaction

[0048] 36mg ATTA (0.05mmol) and 18mg EuCl 3 ·6H 2 O (0.05mmol) dissolved in NaHCO at pH 10.5 3 -NaOH buffer solution, after stirring at room temperature for 2 hours, add 1.2g Na 2 MoO 4 2H 2 O (5 mmol) and 500 μl 30% H 2 o 2 , and stirred for another 30 minutes; observe the change in the fluorescence intensity of the reaction solution, and continue to add H 2 o 2 , until the fluorescence intensity of the reaction solution no longer changes; adjust the pH value of the reaction solution to about 3 with HCl, collect the precipitate by filtration, wash with water and dry in vacuum; ATTA-Eu 3+ and 1 o 2 The internal oxide generated by the reaction (referred to as EP-ATTA-Eu 3+ ) determined by ESI-MS: ESI-MS: m / z (%): 882 (10) [M - -H].

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Abstract

The present invention relates to a new-type singlet oxygen europium fluorescent probe and its application. It is a coordination compound formed by using trivalent europium ion Eu3+ and 2, 2í»:6í»2íŒ-ditripyridine skeleton structure ligand containing functional group. Said invention also provides the structure formula of the described ligand. Said coordination compound can be used for making fluorescent determination of singlet oxygen.

Description

technical field [0001] The present invention relates to singlet oxygen ( 1 o 2 ) measurement technology, specifically a new 1 o 2 Europium complex fluorescent probe (that is, a novel singlet oxygen fluorescent probe based on europium complex) and its application. Background technique [0002] singlet oxygen ( 1 o 2 ) is an excited state of oxygen molecule, it is not only a very useful oxidant in organic synthesis, but also has very important physiological activity. In organic synthesis, 1 o 2 It makes it extremely easy to introduce oxygen into highly stereospecific organic compounds. 1 o 2 There are several important responses: first, 1 o 2 It can react with monoolefins to generate dioxanes or hydrocarbon peroxides. The former usually decomposes into corresponding carbonyl compounds and emits light at room temperature, while the latter generates unsaturated ketones, allyl alcohol or hydroxyl compounds under corresponding conditions. Secondly, 1 o 2 It can reac...

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 袁景利宋波王桂兰
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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