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Oligomeric phenylene ethynylene (OPE) compounds as well as preparation method and application thereof

A technology of oligophenylene vinylene compounds, which is applied in the field of oligopolyphenylene vinylene compounds and their preparation, can solve the problems of strong cytotoxicity, etc., and achieve the effects of increasing water solubility, increasing medicinal value, and simple synthesis route

Inactive Publication Date: 2014-11-19
INST OF NUCLEAR PHYSICS & CHEM CHINA ACADEMY OF
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The study found that EO-OPE with no branched chain and ammonium salt directly connected to the phenyl group has stronger cytotoxicity, and even has a certain degree of bacterial toxicity under non-light conditions

Method used

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  • Oligomeric phenylene ethynylene (OPE) compounds as well as preparation method and application thereof
  • Oligomeric phenylene ethynylene (OPE) compounds as well as preparation method and application thereof
  • Oligomeric phenylene ethynylene (OPE) compounds as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Example 1 . Preparation of Compound (I)

[0033] 1 g (1.98 mmol) of OPE-1 was dissolved in 10 mL of anhydrous dichloromethane, and 396 mg (3.96 mmol) of diisopropylamine was added to obtain a colorless solution. 173 mg (0.99 mmol) e, 21 mg (0.03 mmol) (triphenylphosphine) palladium chloride, and 12 mg (0.06 mmol) cuprous iodide were added sequentially. After 7 hours, add 50 mL of dichloromethane to dilute the reaction system, add 20 mL of saturated ammonium chloride solution for washing, 20 mL of pure water and 20 mL of saturated sodium chloride, collect the organic phase, and wash with an appropriate amount of Dry magnesium sulfate with water for 30 minutes, remove magnesium sulfate by filtration, collect the organic phase, and remove the organic solvent by rotary evaporation under reduced pressure to obtain a light red solid. The solid was passed through a silica gel column to obtain a white solid (dichloromethane:methanol=10:1), yield: 75%. 1 H NMR (600 MHz, DMSO-d ...

Embodiment 2

[0034] Example 2 . Preparation of compound (I)

[0035] 1 g (1.98 mmol) of OPE-1 was dissolved in 10 mL of anhydrous dichloromethane, and 401 mg (3.96 mmol) of triethylamine was added to obtain a colorless solution. 173 mg (0.99 mmol) e, 21 mg (0.03 mmol) bis(triphenylphosphine) palladium chloride, and 12 mg (0.06 mmol) cuprous iodide were added sequentially. After 7 hours, add 50 mL of dichloromethane to dilute the reaction system, add 20 mL of saturated ammonium chloride solution for washing, 20 mL of pure water and 20 mL of saturated sodium chloride, collect the organic phase, and wash with an appropriate amount of Dry magnesium sulfate with water for 30 minutes, remove magnesium sulfate by filtration, collect the organic phase, and remove the organic solvent by rotary evaporation under reduced pressure to obtain a light red solid. The solid was passed through a silica gel column to obtain a white solid (dichloromethane:methanol=10:1), yield: 62%. 1 H NMR (600 MHz, DMSO-...

Embodiment 3

[0036] Example 3 . Preparation of compound (I)

[0037] 1 g (1.98 mmol) of OPE-1 was dissolved in 10 mL of anhydrous dichloromethane, and 396 mg (3.96 mmol) of diisopropylamine was added to obtain a colorless solution. Add 173 mg (0.99 mmol) e, 42 mg (0.06 mmol) (triphenylphosphine) palladium chloride, and 24 mg (0.12 mmol) cuprous iodide in sequence. After 7 hours, add 50 mL of dichloromethane to dilute the reaction system, add 20 mL of saturated ammonium chloride solution for washing, 20 mL of pure water and 20 mL of saturated sodium chloride, collect the organic phase, and wash with an appropriate amount of Dry magnesium sulfate with water for 30 minutes, remove magnesium sulfate by filtration, collect the organic phase, and remove the organic solvent by rotary evaporation under reduced pressure to obtain a light red solid. The solid was passed through a silica gel column to obtain a white solid (dichloromethane:methanol=10:1), yield: 81%. 1 H NMR (600 MHz, DMSO-d 6 ). ...

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Abstract

The invention provides oligomeric phenylene ethynylene (OPE) compounds in formulas (I) and (II) shown in the specification as well as a preparation method and application thereof as photosensitizers in the photo-induced antibacterial process. An OPE molecule with length of about 3.2nm is synthesized by adopting the preparation method and the water solubility of the OPE compounds is increased by a method of introducing amino to the terminal. The OPE compounds have the advantages of simple synthetic routes, mild conditions, universal reagents and high yield, are suitable for amplification production and have good photo-induced antibacterial effects. The antibacterial experiments show that the OPE compounds in the formulas (I) and (II) have good photoactive antibacterial effects, can give play to the antibacterial activities when ultraviolet light and white light are used as light sources for illumination and have weak antibacterial effects without illumination.

Description

technical field [0001] The invention belongs to the technical field of preparation of oligomerized phenylacetylene compounds, and in particular relates to an oligomerized phenylacetylene compound, a preparation method thereof and their application as a photosensitizer in the light-induced antibacterial process. Background technique [0002] Oligophenylene vinylene (OPE) is a kind of compound composed of phenyl and ethynyl alternately and has a large π-conjugated electronic structure. This type of compound has very unique photochemical, photophysical, biophysical and biochemical properties, and the synthesis method is simple and convenient. [0003] The Whitten research group synthesized two asymmetric OPEs and two symmetrical OPEs in 2009 (Tang, Zhou, et al., J. Photochem. Photobiol. A: Chemistry , 2009, 207 , 4-6.), and its supramolecular self-assembly properties were studied in detail. They found that positively charged OPE molecules are more likely to undergo supramole...

Claims

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Application Information

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IPC IPC(8): C07C213/08C07C217/20A61K41/00A61P31/04
Inventor 周志军王静魏洪源蹇源王关全
Owner INST OF NUCLEAR PHYSICS & CHEM CHINA ACADEMY OF