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AIE photosensitizer based on pyridinium salt as well as preparation method and application of AIE photosensitizer

A pyridinium salt and photosensitizer technology, applied in the field of biomedical materials, can solve problems such as imperfect photosensitizer material system, and achieve the effects of excellent antibacterial performance, bacteria promotion, and high yield

Active Publication Date: 2022-05-27
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Although AIE molecules have the advantages of significant aggregation and luminescence enhancement, the reported photosensitizer material system with AIE properties is still incomplete, and there are only a handful of AIE photosensitizers that can simultaneously generate efficient free radical active oxygen.

Method used

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  • AIE photosensitizer based on pyridinium salt as well as preparation method and application of AIE photosensitizer
  • AIE photosensitizer based on pyridinium salt as well as preparation method and application of AIE photosensitizer
  • AIE photosensitizer based on pyridinium salt as well as preparation method and application of AIE photosensitizer

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Experimental program
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preparation example Construction

[0053] The invention provides a kind of preparation method of AIE photosensitizer based on pyridinium salt, comprising the following steps:

[0054] (1) with R 1 The triphenylamine and dibromo-substituted co-receptor A are raw materials, and the unilateral bromine-substituted product is obtained through a coupling reaction;

[0055] (2) reacting the unilateral bromine-substituted product with pinacol biboronate under the action of a catalyst to obtain compound A, and reacting compound A with pyridine derivatives to obtain an intermediate product;

[0056] (3) The AIE photosensitizer based on pyridinium salt is obtained by reacting the intermediate product obtained in step (2) with malononitrile and forming a salt.

[0057] In the present invention, in the step (1), with R 1 The molar ratio of the donor-substituted triphenylamine and the dibromo-substituted co-acceptor A is 1:1.5-2.5, preferably 1:2.0.

[0058] In the present invention, the catalyst for the coupling reaction...

Embodiment 1

[0072] AIE photosensitizer based on pyridinium salt (TBZPyI)

[0073]

[0074] The synthetic route is as follows:

[0075]

[0076] (Diphenylamino)phenylboronic acid (1.45g, 5mmol), 4,7-dibromo-2,1,3-benzothiadiazole (3.00g, 10mmol), Pd(PPh) 3 ) 4 (288.89mg, 0.25mmol) and K 2 CO 3 (6.90 g, 50 mmol) dissolved in a THF / water mixture (v / v=60 / 20). Reaction at 60°C, N 2 The reaction was carried out under the atmosphere for 12 hours. After cooling the reaction mixture to ambient temperature, it was extracted three times with DCM and washed with water. The DCM layer was separated and the Na 2 SO 4 dry. After evaporation of the solvent, the crude product was isolated and purified by column chromatography using petroleum ether / DCM (2 / 1, v / v) as eluent to give TBZ-Br as an orange solid (1.81 g, 79% yield).

[0077] 1 HNMR (500MHz, CDCl 3 )δ7.89(d,J=7.6Hz,1H),7.80(d,J=8.7Hz,2H),7.54(d,J=7.6Hz,1H),7.30(t,J=7.9Hz,4H) , 7.19 (dd, J=8.1 Hz, 6H), 7.08 (t, J=7.3 Hz, 2H).

...

Embodiment 2

[0086] Efficient AIE photosensitizer based on pyridinium salt (CTBZPyI).

[0087]

[0088] The synthetic route is as follows:

[0089]

[0090] 4,4'-Dimethoxy-4"-boronic acid triphenylamine (1.62 g, 4.64 mmol), 4,7-dibromo-2,1,3-benzothiadiazole (2.726 g, 9.28 mmol), Pd(PPh 3 ) 4 (160.74 mg, 0.14 mmol) and K 2 CO 3 (6.41 g, 46.4 mmol) dissolved in a THF / water mixture (v / v=60 / 20). Reaction at 60°C, N 2 The reaction was carried out under the atmosphere for 12 hours. After cooling the reaction mixture to ambient temperature, it was extracted three times with DCM and washed with water. The DCM layer was separated and the Na 2 SO 4 dry. After evaporation of the solvent, the crude product was isolated and purified by column chromatography using petroleum ether / DCM (2 / 1, v / v) as eluent to give CTBZ-Br (1.05 g, 43.75% yield) as an orange solid.

[0091] 1 HNMR (500MHz, CDCl 3 )δ7.87(d,J=7.6Hz,1H),7.75(s,2H),7.56-7.46(m,1H),7.21-6.95(m,6H),6.87(d,J=7.4Hz,4H ),3.81(s...

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Abstract

The invention provides an AIE photosensitizer based on pyridinium salt as well as a preparation method and application of the AIE photosensitizer, and belongs to the technical field of biomedical materials. In the AIE photosensitizer provided by the invention, the triphenylamine derivative serving as a donor not only has very strong electron donating ability, but also has a typical propeller structure, and endows a material with an aggregation-induced emission (AIE) property. A novel acceptor-pyridinium group with stronger electron accepting capability is introduced through pyridine cationization, so that better HOMO-LUMO separation and lower delta EST are realized, and a more effective ISC process is promoted. In addition, an intramolecular charge transfer (ICT) effect is also increased by introducing a cation acceptor, the separation and transfer capabilities of electrons are enhanced, and the generation of I-type ROS is greatly promoted. Experimental results show that the AIE photosensitizer based on the pyridinium salt has efficient ROS generation efficiency, especially efficient HO. Generation efficiency.

Description

technical field [0001] The invention relates to the technical field of biomedical materials, in particular to an AIE photosensitizer based on a pyridinium salt and a preparation method and application thereof. Background technique [0002] Photodynamic therapy has received extensive attention as an emerging non-invasive treatment modality. PDT kills cancer cells or microorganisms by combining photosensitizers, light and oxygen accumulated at the disease site to generate a series of photochemical reactions to generate toxic reactive oxygen species (ROS). Upon light irradiation, the photosensitizer can be excited to its singlet excited state, from which it can fluoresce by radiative transition or undergo intersystem crossing (ISC) to the triplet state and further react with the surrounding oxygen or substrate, Generate ROS. As a highly toxic substance, ROS can trigger the death of microorganisms in various ways. In addition, the short radius of action and longevity of react...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/10A61K41/00A61P31/04
CPCC07D417/10A61K41/0057A61P31/04Y02E10/542
Inventor 唐本忠冯光雪刘珊珊秦安军王柄楠
Owner SOUTH CHINA UNIV OF TECH
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