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Photosensitizer with AIE effect and high singlet oxygen yield and preparation method thereof

A singlet oxygen and photosensitizer technology, applied in the field of photosensitizers, can solve the problems of low singlet oxygen generation efficiency, fluorescence quenching, and short fluorescence emission wavelength, so as to avoid fluorescence quenching, large Stokes shift, and improve The effect of resolution

Active Publication Date: 2022-08-02
SOUTH CHINA UNIV OF TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] In order to overcome the above-mentioned shortcomings and deficiencies of the prior art, the object of the present invention is to provide a photosensitizer with AIE effect and high singlet oxygen yield, which can effectively solve the problem of short fluorescence emission wavelength and singlet oxygen in the prior art. Problems such as low production efficiency and fluorescence quenching caused by aggregation

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  • Photosensitizer with AIE effect and high singlet oxygen yield and preparation method thereof
  • Photosensitizer with AIE effect and high singlet oxygen yield and preparation method thereof
  • Photosensitizer with AIE effect and high singlet oxygen yield and preparation method thereof

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Embodiment 1

[0044] A preparation method of a photosensitizer with AIE effect and high singlet oxygen yield of the present embodiment, the synthetic route is as follows figure 1 The specific synthesis steps are as follows:

[0045] (1) Preparation of Intermediate 1

[0046] Combine (2 mmol, 0.59 g) 4,7-dibromo-2,1,3-benzothiadiazole, (2 mmol, 0.31 g) 5-aldol-2-thiopheneboronic acid, 5 mL of 2M aqueous potassium carbonate and 50 mL of tetrahydrofuran Add in the reactor, use tetrakis(triphenylphosphine) palladium as catalyst, under the protection of inert gas, react at 80 ° C for 12 hours, after the reaction is completed, add water to dilute, extract with dichloromethane, use n-hexane: dichloromethane =1:1, v / v is the eluent and passed through the column to obtain 0.46 mmol, 0.15 g of intermediate 1, and the yield is 23%.

[0047] (2) Preparation of Intermediate 2

[0048] (1 mmol, 0.33 g) Intermediate 1, (1 mmol, 0.29 g) triphenylamine-4-boronic acid, 10 mL of 2M aqueous potassium carbon...

Embodiment 2

[0064] A preparation method of a photosensitizer with AIE effect and high singlet oxygen yield of the present embodiment, the synthetic route is as follows figure 1 The specific synthesis steps are as follows:

[0065] (1) Preparation of Intermediate 1

[0066] Combine (5 mmol, 1.47 g) 4,7-dibromo-2,1,3-benzothiadiazole, (8 mmol, 1.25 g) 5-aldol-2-thiopheneboronic acid, 15 mL of 2M aqueous potassium carbonate and 50 mL of tetrahydrofuran Add in the reactor, use tetrakis (triphenylphosphine) palladium as catalyst, under the protection of inert gas, react at 90 ℃ temperature for 24 hours, after the reaction is finished, add water for dilution, dichloromethane extraction, with n-hexane: dichloromethane =2:1, v / v is the eluent and passed through the column to obtain 1.35 mmol, 0.44 g of intermediate 1, and the yield is 27%.

[0067] (2) Preparation of Intermediate 2

[0068] (1.5mmol, 0.49g) Intermediate 1, (1.8mmol, 0.52g) triphenylamine-4-boronic acid, 10mL 2M aqueous potassi...

Embodiment 3

[0074] A kind of preparation method of photosensitizer with AIE effect and high singlet oxygen yield, the synthetic route is such as figure 1 The specific synthesis steps are as follows:

[0075] (1) Preparation of Intermediate 1

[0076] Combine (10 mmol, 2.94 g) 4,7-dibromo-2,1,3-benzothiadiazole, (15 mmol, 2.34 g) 5-aldehyde-2-thiopheneboronic acid, 20 ml of 2M aqueous sodium carbonate and 70 ml of tetrahydrofuran Add in the reactor, use tetrakis (triphenylphosphine) palladium as catalyst, under the protection of inert gas, react at 90 ℃ temperature for 24 hours, after the reaction is finished, add water for dilution, dichloromethane extraction, with n-hexane: dichloromethane =2:1, v / v is the eluent and passed through the column to obtain 3.12 mmol, 1.01 g of intermediate 1, and the yield is 31.2%.

[0077] (2) Preparation of Intermediate 2

[0078] (2mmol, 0.65g) Intermediate 1, (3mmol, 0.87g) triphenylamine-4-boronic acid, 20mL 2M aqueous sodium carbonate solution, 40m...

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Abstract

According to the photosensitizer with the AIE effect and the high singlet oxygen yield, an electricity-absorbing indole onium salt structure and electricity-supplying triphenylamine are introduced into the 4 site and the 7 site of benzothiadiazole respectively to form an electricity-supplying-electricity-absorbing structure (D-A), the intramolecular charge transfer effect is enhanced, and the photosensitizer has the AIE effect and is high in singlet oxygen yield. The fluorescence emission wavelength red shift and the obvious improvement of the singlet oxygen yield are promoted. The invention further discloses a preparation method of the photosensitizer with the AIE effect and the high singlet oxygen yield. The method effectively solves the problems of fluorescence quenching, low singlet oxygen yield and the like caused by short fluorescence emission wavelength and aggregation in the prior art, and has a wide application prospect in the aspect of photodynamic therapy.

Description

technical field [0001] The invention relates to the technical field of photosensitizers, in particular to a photosensitizer with AIE effect and high singlet oxygen yield and a preparation method thereof. Background technique [0002] In recent years, cancer has become one of the leading causes of human death and has received close attention due to its low survival rate and widespread prevalence worldwide. Traditional cancer treatment methods include surgical resection, chemotherapy, targeted therapy, and radiation therapy, etc., but these methods have major limitations, such as large trauma, incomplete treatment, and large side effects. Therefore, photodynamic therapy has become the frontier of research due to its non-invasiveness, negligible drug resistance and low side effects. [0003] Photodynamic therapy is the use of photosensitizers to generate reactive oxygen species under light to kill tumor cells, thereby treating tumors. Short fluorescence emission wavelength, l...

Claims

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Application Information

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IPC IPC(8): C07D417/14C09K11/06A61K41/00
CPCC07D417/14C09K11/06A61K41/0057C09K2211/1007C09K2211/1014C09K2211/1029C09K2211/1051C09K2211/1092Y02E10/542
Inventor 瞿金清蒋超高焱阳
Owner SOUTH CHINA UNIV OF TECH
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