A kind of benzothiadiazole-tb compound and its synthesis method and application

A technology of benzothiadiazole and synthesis method, applied in the field of analytical chemistry, can solve problems such as visible absorption and poor penetration, and achieve the effects of excellent solid-state luminescence, expanded types, and wide pH applicable range

Active Publication Date: 2022-05-10
XUZHOU NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In view of the problems of visible absorption and poor penetration of traditional PDT photosensitizers, more and more new high-efficiency photosensitizers have been developed.
However, photosensitizers based on TB skeletons are still in their infancy, with only one related report

Method used

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  • A kind of benzothiadiazole-tb compound and its synthesis method and application
  • A kind of benzothiadiazole-tb compound and its synthesis method and application
  • A kind of benzothiadiazole-tb compound and its synthesis method and application

Examples

Experimental program
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Embodiment

[0060]In this example, p-bromoaniline, paraformaldehyde, n-butyllithium, 4,7-dibromo-benzothiadiazole, etc. are used as raw materials to prepare through coupling reaction. Include the following steps:

[0061] Compound 1 or 2 reacts with paraformaldehyde to obtain intermediate 3 or 4, intermediate 3 or 4 reacts with trimethyl borate to obtain intermediate 5 or 6, intermediate 5 or 6 and 2,7-dibromo-benzothiophene Compound 8 or 9 can be obtained by coupling reaction of oxadiazole (7), and compound 10 can be obtained by further hydrolysis of 9.

[0062] By above-mentioned synthetic method, prepare the compound of following embodiment:

[0063] (1) Add 4-bromoaniline 1 (50.0mmol) and paraformaldehyde (100.0mmol) into a 200.0mL round-bottomed flask in turn, place it in a low-temperature tank and adjust the temperature to -15°C, and slowly add it dropwise into the flask while stirring After trifluoroacetic acid (100.0 mL, added dropwise in about 30 min), react at room temperature...

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Abstract

The present invention provides a benzothiadiazole-TB compound and its synthesis method and application. Its general structural formula is shown in formula A: wherein, R is one of hydrogen, alkoxyl, hydroxyl, and alkyl. The benzothiadiazole-TB compound has a large Stokes shift, exhibits excellent luminescent properties, has excellent solid-state luminescence, and has the potential to become an excellent OLED material; it has a wide pH range and can be applied to In the human physiological environment; effective and good response to viscosity, it may become a fluorescent probe for viscosity response; for Fe 3+ Possesses the ability to recognize and is expected to become an excellent Fe 3+ Fluorescent probe: has good PDT effect, and can stain and image A549 cells, expands the types of photosensitizers, and provides a new idea for the synthesis of photosensitizers for imaging-guided PDT.

Description

technical field [0001] The invention belongs to the field of analytical chemistry, and in particular relates to the synthesis of a class of benzothiadiazole-TB derivatives with excellent optical properties and its application in metal ion recognition, photodynamic therapy and biological imaging. Background technique [0002] Photodynamic therapy (Photodynamic Therapy, PDT) is a new method of treating tumors and other diseases with photosensitizing drugs and laser activation. Compared with traditional methods, it has the advantages of low side effects, minimal invasiveness, no obvious drug resistance, high tumor destruction selectivity, and easy combination with other therapies. Photodynamic therapy (PDT) has good spatiotemporal accuracy and effectiveness in clinical research and treatment, and has become an important emerging means of clinical tumor precision treatment. With the rapid development of PDT, people have higher and higher requirements for the diversity of photos...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/08A61K41/00A61P35/00C09K11/06G01N21/64
CPCC07D487/08C09K11/06A61K41/0057A61P35/00G01N21/6428C09K2211/1051C09K2211/1044G01N2021/6432
Inventor 吴翚苑睿周杭宛瑜张鹏
Owner XUZHOU NORMAL UNIVERSITY
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