Ligand for aggregation-induced emission and complexes

A technology of aggregation-induced luminescence and complexes, which is applied in the direction of luminescent materials, compounds of group 5/15 elements of the periodic table, preparations for in vivo tests, etc., and can solve problems such as overlap and interference of fluorescence emission spectra, and inability to obtain information

Active Publication Date: 2016-09-07
WUHAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

When the system contains a variety of fluorescent substances, because the fluorescence emission spectra of each substance may overlap and i

Method used

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  • Ligand for aggregation-induced emission and complexes
  • Ligand for aggregation-induced emission and complexes
  • Ligand for aggregation-induced emission and complexes

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0059] Embodiment 1, zinc, cadmium complex is used for the detection of nucleic acid

[0060] Synthesis of complex Zn1:

[0061]

[0062] Synthesis of Ligand 5: Put the raw material A1 (0.46g, 1mmol) and fenneline (0.69g, 4mmol) into a single-necked round-bottomed flask, add 40mL of anhydrous acetonitrile, reflux for 1 day, and distill under reduced pressure. After separation by column chromatography, 0.39 g of the target product was obtained with a yield of 71%. ESI-MS:m / z[M+H] + :547.Anal.Calcd for C 36 h 42 N 4 O: C, 79.08; H, 7.74; N, 10.25; Found: C, 78.94; H, 7.58; N, 10.07.

[0063] Preparation of complex Zn1: Dissolve 107mg (0.2mmol) of ligand 5 in 0.5mL methanol solution, and weigh Zn(NO 3 ) 2 ·6H 2 O 84mg (0.3mmoL) was dissolved in 0.5mL of methanol solution. The methanol solution of zinc nitrate was slowly added dropwise to the methanol solution of Ligand 5, during which a white solid was produced and precipitated, left for a period of time, filtered wit...

Embodiment 2

[0075] Embodiment 2, preparation and time-resolved detection of rare earth complexes

[0076] The synthetic route of complex Eu1 is as follows:

[0077]

[0078] Preparation of Ligand 8: Ligand 5 (0.08 g, 0.146 mmol), 2-chloro-N,N-diethylacetamide (0.11 g, 0.74 mmol), potassium iodide (0.20 g, 1.2 mmol) were added to a round bottom flask ), potassium carbonate (0.22g, 1.6mmol) and 10mL of acetonitrile, reflux reaction under argon protection for 48h, concentrated under reduced pressure, using chloroform-methanol (v:v=20:1) as eluent, passed through a silica gel column Purified by chromatography to obtain 0.12 g of a colorless oily liquid with a yield of 93%. ESI-MS:m / z[M+H] + :886,[M+Na] + :908.

[0079] Preparation of complex Eu1: Add ligand 8 (0.048g, 0.053mmol), hexahydrate, europium trichloride (0.022g, 0.06mmol) and 2.5mL methanol to a one-necked bottle, and reflux for 15h, then collect the filtrate by filtration. Distilled under reduced pressure to obtain a yellow...

Embodiment 3

[0086] Embodiment 3, the synthesis of magnetic contrast agent

[0087] The synthetic routes of ligand 9 and ligand 10 are as follows:

[0088]

[0089] Synthesis of Ligand 9: Ligand 5 (0.11g, 0.2mmol), tert-butyl bromoacetate (0.4g, 4mmol) and 10mL of acetonitrile were added to a round-bottomed flask. (v:v=20:1) was used as the eluent, and purified by silica gel column chromatography to obtain 0.15 g of a colorless oily liquid with a yield of 84%. ESI-MS:m / z[M+H] + :889.

[0090] Synthesis of Ligand 10: Ligand 9 (0.09 g, 0.1 mmol) and 5 mL of concentrated hydrochloric acid were added to a round bottom flask, stirred for 4 h, then concentrated under reduced pressure at 70°C to obtain about 0.06 g of white solid product with a yield of 83%. ESI-MS:m / z[M-H] - :719.

[0091] By implementing the method in Example 2, the ligand 10 was mixed with EuCl 3 , GdCl 3 , MnCl 2 reaction, the corresponding complex can be obtained, the structure is as follows:

[0092]

[0093]...

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Abstract

The invention relates to a ligand for aggregation-induced emission and metal complexes thereof, belonging to the field of biological detection. The ligand simultaneously comprises a macrocyclic amine group and a group for aggregation-induced emission (AIE), wherein both the groups are covalently linked or bridged through common organic units. According to different metal ions chelated in the ligand, the complexes show different functions, wherein the complexes of zinc, cadmium and the like can be used as anion fluorescent probes and applied in detection of molecules like nucleic acid and protein; the complexes of lanthanide metals can be applied in fluorescent and phosphorescent detection and imaging for time resolution; and the complexes of paramagnetic metals can be applied in magnetic resonance imaging.

Description

technical field [0001] The invention relates to an aggregation-induced luminescent ligand and a metal complex thereof, which can be used as probe molecules for fluorescence detection, fluorescence imaging of cells or tissues, magnetic resonance imaging, etc., and belong to the field of biological detection. Background technique [0002] Aggregation-induced emission (AIE) refers to a photophysical phenomenon in which a class of fluorescent chromophores emit weakly or even no light in the solution state, but the fluorescence is significantly enhanced in the solid-state or aggregated state. Since the fluorescent substance is in the solution, the molecular aggregation degree is small, the groups inside the molecule can rotate freely, and most of the light absorbed by the molecule is released in the form of heat energy, so the AIE fluorescent substance does not fluoresce in the solution. In recent years, a large number of organic molecules with AIE characteristics have been synth...

Claims

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Application Information

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IPC IPC(8): C07D295/088C07D295/15C07D403/06C07F9/6524C09K11/06G01N21/64A61K49/10
CPCA61K49/085A61K49/106A61K49/108C07D295/088C07D295/15C07D403/06C07F9/6524C09K11/06C09K2211/182C09K2211/188G01N21/6486
Inventor 杨楚罗朱泽策王胜
Owner WUHAN UNIV
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