Benzothiadiazole-TB compound as well as synthesis method and application thereof

A technology of benzothiadiazole and compounds, which is applied in the field of synthesis of benzothiadiazole-TB derivatives, can solve the problems of visible absorption and poor penetration, achieve excellent solid-state luminescence, convenient post-processing, and expand types Effect

Active Publication Date: 2021-09-21
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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  • Benzothiadiazole-TB compound as well as synthesis method and application thereof
  • Benzothiadiazole-TB compound as well as synthesis method and application thereof
  • Benzothiadiazole-TB compound as well as synthesis method and application thereof

Examples

Experimental program
Comparison scheme
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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 invention provides a benzothiadiazole-TB compound as well as a synthesis method and application thereof; the structural general formula of the benzothiadiazole-TB compound is represented by a formula A, wherein R is one of hydrogen, alkoxy, hydroxyl and alkyl. The benzothiadiazole-TB compound has characteristics of large Stokes displacement, excellent luminescence property, excellent solid state luminescence, and potential of becoming an excellent OLED material; the benzothiadiazole-TB compound has a wide pH application range and can be applied to a human physiological environment; the benzothiadiazole-TB compound has effective and good response to viscosity, and has the possibility of becoming a viscosity response fluorescent probe; the benzothiadiazole-TB compound has recognition capability on Fe<3+> and is expected to become an excellent Fe<3+> fluorescent probe; and the benzothiadiazole-TB compound has a good PDT effect, can perform dyeing imaging on A549 cells, expands the variety of photosensitizers, and provides a new thought for synthesizing imaging-guided PDT photosensitizers.

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 Applications(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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