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A highly selective aggregation-induced chemiluminescent probe for singlet oxygen, its preparation method and application

A chemiluminescence, aggregation-induced technology, applied in chemical instruments and methods, organic chemistry, luminescent materials, etc., can solve the problems of low body content and short singlet oxygen life, achieve high selectivity, and ensure the effect of energy transfer efficiency

Inactive Publication Date: 2021-03-30
SHAANXI NORMAL UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Detecting singlet oxygen in cells and living organisms is a challenge due to its short lifetime and extremely low levels in vivo

Method used

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  • A highly selective aggregation-induced chemiluminescent probe for singlet oxygen, its preparation method and application
  • A highly selective aggregation-induced chemiluminescent probe for singlet oxygen, its preparation method and application
  • A highly selective aggregation-induced chemiluminescent probe for singlet oxygen, its preparation method and application

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Embodiment 1

[0031] 1. Add 10.09g (0.06mol) of diphenylmethane (0.06mol) and 250mL of dry tetrahydrofuran into a 500mL three-necked flask, vacuum replace, cool to 0°C, keep stirring, and slowly add 24.0mL2.5mol into the mixture with a syringe under nitrogen protection. / L (0.06mol) cyclohexane solution of n-butyllithium, continue to stir for 30min after adding, then add 40mL of dry tetrahydrofuran solution containing 15.14g (0.058mol) 4-bromobenzophenone dropwise, at room temperature Stir for 10 h, then add ammonium chloride aqueous solution to the reaction mixture to stop the reaction, extract with dichloromethane (300 mL x 3 times), combine the organic phases, and wash alternately with saturated sodium chloride aqueous solution and deionized water (300 mL x 3 times) , and then dried with anhydrous magnesium sulfate, filtered, and the solvent was evaporated to obtain the intermediate 2-(4-bromophenyl)-1,1,2-triphenylethanol. The obtained intermediate and 1.0 g of anhydrous p-toluenesulfon...

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Abstract

The invention discloses a high-selectivity aggregation induced chemiluminiscence probe for <1>O2 as well as a preparation method and an application of the chemiluminiscence probe. The structural formula of the chemiluminiscence probe is shown in the description, and the chemical name is 6-(4-(1,2,2-triphenylethyl)phenyl)-2,3-dihydrophthalazine-1,4-dione (TPE-PH for short). Chemiluminiscence of theprobe is weak when a solution is formed by the probe in a good solvent such as tetrahydrofuran. In a tetrahydrofuran-water mixed solvent, when proportion of water is larger than 70% (V / V), chemiluminiscence produced when formed nano-aggregate is oxidized by <1>O2 is enhanced sharply with increase of the proportion of water in the mixed solvent, the probe has typical aggregation induced reinforcedchemiluminiscence characteristic, and emission wavelength peak is 485 nm. The TPE-PH nano-aggregate has quite high chemiluminiscence selectivity for <1>O2 under physiological conditions and can recognize <1>O2 on nanomole level, which proves that TPE-PH is a novel chemiluminiscence probe capable of recognizing and detecting <1>O2 with high selectivity and high sensitivity in a physiological system.

Description

technical field [0001] The invention belongs to the technical field of chemiluminescence detection, and in particular relates to a novel chemiluminescence probe with aggregation-induced luminescence properties, a preparation method of the probe and an application in selective recognition of singlet oxygen. Background technique [0002] singlet oxygen ( 1 o 2 ) is a highly reactive transient intermediate produced during biological metabolism. Singlet oxygen can penetrate the mitochondrial membrane or nuclear membrane, and can react rapidly with many biomolecules such as DNA, lipids, free amino acids and proteins. Under normal circumstances, the generation and removal of singlet oxygen in cells is in a state of dynamic balance, and the level of singlet oxygen is very low, so it will not cause harm to the body. However, once this dynamic balance is disrupted, the excessive production of singlet oxygen will lead to membrane lipid peroxidation or degreasing, DNA damage and oth...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D237/32C09K11/06G01N21/64
CPCC07D237/32C09K11/06C09K2211/1044G01N21/643
Inventor 吕家根张胜海崔红波谷旻张艳玲李胤涛吴兆熠廖婷
Owner SHAANXI NORMAL UNIV
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