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Bipyridine ligand containing AIE and ACQ groups, amphiphilic rhombic supramolecular metal ring and application of amphiphilic rhombic supramolecular metal ring

A bipyridine and amphiphilic technology, applied in the field of pharmaceutical preparations, can solve the problems of inapplicability for biological imaging, increase water solubility and biocompatibility, etc., and achieve good coordinated fluorescence emission, convenient cell imaging, and clear cell imaging effects. Effect

Pending Publication Date: 2022-04-12
HANGZHOU NORMAL UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

CN112142811A An amphiphilic diamond-shaped supramolecular metal macrocycle and its preparation method and application are the inventor's previous research. This patent proposes an amphiphilic diamond-shaped supramolecular metal macrocycle, which is formed by self-assembly of directional coordination bonds , modified with glucose groups to increase water solubility and biocompatibility, and then applied in the field of drug carriers, but it is not suitable for bioimaging

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  • Bipyridine ligand containing AIE and ACQ groups, amphiphilic rhombic supramolecular metal ring and application of amphiphilic rhombic supramolecular metal ring
  • Bipyridine ligand containing AIE and ACQ groups, amphiphilic rhombic supramolecular metal ring and application of amphiphilic rhombic supramolecular metal ring
  • Bipyridine ligand containing AIE and ACQ groups, amphiphilic rhombic supramolecular metal ring and application of amphiphilic rhombic supramolecular metal ring

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Embodiment 1

[0116] Example 1. Preparation of 120° Bipyridine Ligands Containing Aggregation-Induced Emission (AIE) and Aggregation Fluorescence Quenching (ACQ) Groups

Embodiment 1-1

[0117] Example 1-1: Bispyridine ligand 1a

[0118]

[0119] Step (1), the preparation of compound 6:

[0120] Compound 4 (1000.0mg, 5.61mmol), compound 5 (1139.8mg, 3.03mmol), potassium carbonate (1396.0mg, 10.10mmol), tetrakis (triphenylphosphine) palladium (26.4mg, 0.02mmol) was added to a 250mL Add a mixed solvent (1,4-dioxane / water, 4 / 1, v / v) to the Schlenk bottle to dissolve, then use liquid nitrogen and nitrogen gas to deoxygenate three times, and store at 80°C under the protection of argon The reaction was heated for 48 hours. After the reaction was finished, cool to room temperature, concentrate under reduced pressure with a rotary evaporator, and extract three times with dichloromethane, collect the organic phase, dry and filter to obtain the crude product, which was separated and purified by silica gel chromatography (petroleum ether / ethyl acetate, 6 / 1, v / v), finally obtained a yellow solid (705.0mg, 43.4%), melting point: 247.7-250.1°C.

[0121] Figure 1-3 S...

Embodiment 1-2

[0128] Example 1-2: Bispyridine ligand 1b

[0129]

[0130] Step (1), the preparation of compound 6:

[0131] Compound 4 (1000.0mg, 5.61mmol), compound 5 (1139.8mg, 3.03mmol), potassium carbonate (1396.0mg, 10.10mmol), tetrakis (triphenylphosphine) palladium (26.4mg, 0.02mmol) was added to a 250mL Add a mixed solvent (1,4-dioxane / water, 4 / 1, v / v) to the Schlenk bottle to dissolve, then use liquid nitrogen and nitrogen gas to deoxygenate three times, and store at 80°C under the protection of argon The reaction was heated for 48 hours. After the reaction was finished, cool to room temperature, concentrate under reduced pressure with a rotary evaporator, and extract three times with dichloromethane, collect the organic phase, dry and filter to obtain the crude product, which was separated and purified by silica gel chromatography (petroleum ether / ethyl acetate, 6 / 1, v / v), finally obtained a yellow solid (705.0mg, 43.4%), melting point: 247.7-250.1°C.

[0132] Figure 1-3 S...

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Abstract

The invention discloses a bispyridine ligand containing AIE and ACQ groups, an amphipathic rhombic supramolecular metal ring and application of the amphipathic rhombic supramolecular metal ring. The preparation method comprises the following steps: dissolving a bipyridine ligand 1 containing AIE and ACQ groups and a diplatinum receptor 2 in an alcohol solvent, and heating at 40-60 DEG C to react for 10-15 hours; and after the reaction is finished, carrying out post-treatment to obtain the amphiphilic rhombic supramolecular metal ring 3. The invention relates to an application of an amphiphilic rhombic supramolecular metal ring containing aggregation-induced emission (AIE) and aggregation fluorescence quenching (ACQ) groups at 120 DEG C as a fluorescent dye in biological imaging.

Description

technical field [0001] The invention belongs to the field of pharmaceutical preparations, and relates to a bipyridine ligand containing AIE and ACQ groups, an amphipathic rhombic supramolecular metal ring and its application. Background technique [0002] In recent years, materials with tunable fluorescence emission have attracted increasing attention and have broad applications in organic tunable diodes, bioimaging, fluorescent sensors, and photovoltaic cells. There are usually two design methods for such materials: (1) mixing dyes with different color emissions; (2) linking multiple fluorophores with different emissions through covalent or non-covalent bonds to obtain single-molecule dyes. Compared with hybrid dyes, single molecules have the advantages of better reproducibility, stability, and ease of fabrication. However, in situ coordinated emission from single molecules remains challenging because it is difficult to integrate multiple fluorophores with different staini...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/38C07F15/00C09K11/06G01N21/64
CPCC07D213/38C09K11/06G01N21/64C07F15/00
Inventor 尹守春范逸錡李洋何田
Owner HANGZHOU NORMAL UNIVERSITY
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