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Novel ligand for copper ion detection, preparation of novel ligand, novel ruthenium complex and near-infrared long-life fluorescent probe

A technology of complexes and copper ions, applied in ruthenium organic compounds, compounds containing elements of Group 8/9/10/18 of the periodic table, fluorescence/phosphorescence, etc., can solve short emission wavelength, low detection limit, probe Complicated synthesis steps, etc.

Active Publication Date: 2020-10-23
GUANGDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These probes can effectively identify copper ions, but the disadvantages are that the synthesis steps of the probes are cumbersome, the detection limit is low, the emission wavelength is short, the fluorescence lifetime is generally only tens of nanoseconds, and super-resolution imaging of deep tissues cannot be realized.

Method used

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  • Novel ligand for copper ion detection, preparation of novel ligand, novel ruthenium complex and near-infrared long-life fluorescent probe
  • Novel ligand for copper ion detection, preparation of novel ligand, novel ruthenium complex and near-infrared long-life fluorescent probe
  • Novel ligand for copper ion detection, preparation of novel ligand, novel ruthenium complex and near-infrared long-life fluorescent probe

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preparation example Construction

[0032] The present invention also provides a method for preparing the ligand of the structure shown in formula (I), comprising:

[0033] 2-imidazole formaldehyde and o-phenanthroline-5,6-diamine mixed reaction, obtain the ligand of structure shown in formula (I),

[0034]

[0035] According to the present invention, the present invention mixes and reacts 2-imidazole formaldehyde and o-phenanthroline-5,6-diamine to obtain the ligand of the structure shown in formula (I), wherein the present invention has no special requirements for the solvent of the mixed reaction , such as ethanol; the reaction temperature is 60-90°C, more preferably 70-80°C.

[0036] The present invention also provides a complex composed of anions and cations, wherein the cations are composed of a main ligand, an auxiliary ligand and a transition metal,

[0037] Wherein, the main ligand has a structure shown in formula (I);

[0038]

[0039] In the present invention, the auxiliary ligand is preferabl...

Embodiment 1

[0053] The synthesis of embodiment 1 ligand 2-pbm

[0054] 1.2mmol (0.116g) of 2-imidazole formaldehyde was heated and dissolved in 2.5mL of absolute ethanol, and 2.5mL of ethanol in which 1.5mmol (0.314g) of o-phenanthroline-5,6-diamine was dissolved was added dropwise. The solution was added in half an hour, the mixed solution was refluxed, reacted for 6 hours, cooled and filtered with suction, the obtained solid was washed with absolute ethanol and anhydrous ether, and dried in vacuum to obtain the ligand 2-pbm.

Embodiment 2

[0055] The preparation of embodiment 2 complex (Ru-2-pbm)

[0056] 0.142g (0.25mmol) cis-[Ru(phen) 2 Cl 2 ]·2H 2O and 0.100 g (0.25 mmol) of ligand 2-pbm were dissolved in 35 mL of ethanol-water (4:1), and refluxed for 6 h under an argon atmosphere to obtain a red reaction solution. Cool to room temperature, filter, add saturated sodium perchlorate solution dropwise to the filtrate to obtain a red precipitate, stand still, filter with suction, wash with water and ether, and dry in vacuo to obtain the Ru-2-pbm complex.

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Abstract

The invention provides a novel ligand for copper ion detection, preparation of the novel ligand, a novel ruthenium complex and a near-infrared long-life fluorescent probe. Results show, the inventionprovides a complex prepared from a ligand. The emission wavelength is in a near-infrared region, the excited state service life is long, the biocompatibility is good, the complex can be used as a fluorescent probe or test paper to be applied to detection of in-vitro copper ions, can also be used as a fluorescent probe to be applied to detection of in-vivo copper ions, and then is applied to the field of fluorescent bioimaging in life science research, and the detection limit is low; and the preparation method of the complex is simple, is suitable for industrial production, and has a good industrial application prospect.

Description

technical field [0001] The invention relates to the technical field of complexes, in particular to a novel ligand for copper ion detection and its preparation, a novel ruthenium complex and a near-infrared long-life fluorescent probe. Background technique [0002] Copper ion is a trace element necessary for the advanced organs of the human body, and plays an important role in many important physiological processes. Abnormal copper ion metabolism is closely related to the occurrence of Alzheimer's disease, Parkinson's disease and other diseases. The research on copper ion detection reagents is of great significance to the early diagnosis of some diseases. [0003] At present, copper ion detection methods include atomic absorption spectroscopy, inductively coupled atomic emission spectroscopy, inductively coupled plasma mass spectrometry, electrochemical methods, and fluorescence spectroscopy. Among many methods, fluorescence spectroscopy is considered to be the best choice a...

Claims

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Application Information

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IPC IPC(8): C07D471/04C07F15/00C09K11/06G01N21/64
CPCC07D471/04C07F15/0053C09K11/06G01N21/643C09K2211/185C09K2211/1044G01N2021/6432G01N2021/6443
Inventor 赵伟马婉儿于会娟余林
Owner GUANGDONG UNIV OF TECH
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