A kind of oligophenylene vinylene compound and its preparation method and application

A technology for oligophenylene vinylene compounds, which is applied in the field of oligopolyphenylene vinylene compounds and their preparation, can solve problems such as strong cytotoxicity, and achieve the effects of increasing water solubility, high yield, and satisfying preparation conditions

Inactive Publication Date: 2016-08-24
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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  • A kind of oligophenylene vinylene compound and its preparation method and application
  • A kind of oligophenylene vinylene compound and its preparation method and application
  • A kind of oligophenylene vinylene compound and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Example 1. Preparation of compound (I)

[0032]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 sequentially added. 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

[0033] Example 2. Preparation of compound (I)

[0034] 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 to wash, 20 mL of pure water and 20 mL of saturated sodium chloride, collect the organic phase, and wash with an appropriate amount of anhydrous Magnesium sulfate was dried for 30 minutes, the magnesium sulfate was removed by filtration, the organic phase was collected, and the organic solvent was removed 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 ...

Embodiment 3

[0035] Example 3. Preparation of compound (I)

[0036] 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 ). δ...

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Abstract

The invention provides an oligophenylene vinylene compound of formula (I) and formula (II), a preparation method thereof and their application as a photosensitizer in the process of light-induced antibacterial. The preparation method of the present invention is used to synthesize an oligomer phenylene vinylene molecule with a length of about 3.2nm and introduce amino groups through the terminal to increase the water solubility of the oligomer polyphenylene vinylene compound. The oligophenylene vinylene compound has simple synthesis route, mild conditions, common reagents, high yield, is suitable for scale-up production and has good light-induced antibacterial effect. Antibacterial experiments show that the oligophenylene vinylene compounds of formula (I) and formula (II) have good photoactive antibacterial effects, and they can exert antibacterial activity when using ultraviolet light and white light as light sources, but the antibacterial effect is weak when they are not illuminated .

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 supramolecula...

Claims

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Application Information

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Patent Type & Authority Patents(China)
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
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