Organic ligand, rare earth organic fluorescent probe material thereof and preparation method thereof

Abstract

The invention provides a tridentate organic ligand, an organic fluorescent probe material generated from the organic ligand and rare earth ions, and a preparation method of the organic ligand, and also provides water-soluble rare earth fluorescent probes used for bioactive molecule analysis detection or imaging analysis. The structure of the rare earth organic fluorescence probe material is represented by a formula shown in the specification. A red fluorescent probe emits characteristic red fluorescent lights of Eu<3+>, and the strongest emission peak is positioned at 618nm; and a green fluorescent probe emits characteristic green fluorescent lights of Tb<3+>, and the strongest emission peak is positioned at 544nm. The red fluorescent probe has strong excitation absorptions at 377nm, 397nm and 466nm when the red fluorescent probe is used for solid phase analysis of biological molecules, so interferences of biological molecule background fluorescent lights to analytic detection can be avoided, and the sensitivity and the selectivity of the analytic detection method are improved. The green fluorescent probe has strong excitation absorption at 346nm when the green fluorescent probe is used for the solid phase analysis of the biological molecules, so interferences of biological molecule background fluorescent lights to analytic detection can be avoided, and the sensitivity and the selectivity of the analytic detection method are improved.

Description

technical field [0001] The invention relates to a ligand, its fluorescent probe and its preparation method, especially an organic ligand, its rare earth organic fluorescent probe material and its preparation method. technical background [0002] Rare earth fluorescent labeling materials have the characteristics of long life and can be used in time-resolved fluorescence immunoassay. This analysis technique can eliminate the interference of background fluorescence such as biomolecules, thereby greatly improving the sensitivity and selectivity of detection and analysis. It has become one of the most sensitive biodetection techniques and is widely used in fluorescent labeling immunoassays, DNA and other biomolecules. Analysis and detection of biomolecules, disease diagnosis, timely dynamic tracking and detection of biomolecules, in vivo imaging analysis, etc. (Chem. Rev. 2010, 110(5): 2729-2755.). The core technology of time-resolved immunofluorescence analysis and detection te...

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Problems solved by technology

However, for solid samples or dilute solution samples of dicomplexes formed by pyridine-2,6-dicarboxylic acid with Eu3+ and Tb3+, the excitation wavelengths are all at 270- At 280 nm, which coincides with the background absorption wavelength of biomolecules, biomolecules compete with Eu3+ and Tb3+ fluorescent probes to absorb the excitation light energy, so that biomolecules (J Alloys Compd, 2010, 501: 42–46.)

The excitation wavelength of the rare earth complex can be shifted to the long wavelength direction by synthesizing an organic ligand with a larger conjugated structure, but when the triplet energy level of the ligand is close to the lowest excited state energy level of the rare earth ion, electrons from The excited state energy level of the rare earth ion can return to the triplet state energy level of the ligand, so that the luminous efficiency of the rare earth complex decreases

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