Synthesis, photophysics and biomolecule interactive studies of new hybrid benzo-2,1,3-thiadiazoles,New Journal of Chemistry

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Synthesis, photophysics and biomolecule interactive studies of new hybrid benzo-2,1,3-thiadiazoles
New Journal of Chemistry ( IF 2.7 ) Pub Date : 2020/01/15 , DOI: 10.1039/c9nj05932f
José S. S. Neto _{1,

2,

3,

4} , Roberta Krüger _{1,

2,

3,

4} , Renata A. Balaguez _{1,

2,

3,

4} , Mariana G. Fronza _{2,

3,

4,

5,

6} , Thiago V. Acunha _{7,

8,

9,

10,

11} , Robson S. Oliboni _{2,

3,

4,

12} , Lucielli Savegnago _{2,

3,

4,

5,

6} , Bernardo A. Iglesias _{7,

8,

9,

10,

11} , Diego Alves _{1,

2,

3,

4}

Affiliation

Four new hybrid molecules containing benzo-2,1,3-thiadiazole, benzofuran and arylselanyl moieties, named 4,7-bis(3-(arylselanyl)benzofuran-2-yl)benzo[c][1,2,5]thiadiazoles, were designed and synthesized in good yields through an electrophilic cyclization of 4,7-bis((2-methoxyphenyl)ethynyl)benzo[c][1,2,5]thiadiazole 1 and diaryl diselenides 2 using trichloroisocyanuric acid to generate electrophilic arylselanyl species. The photophysical properties of compounds 3a–d were investigated using UV-vis absorption and emission fluorescence analysis. The emission fluorescence analysis showed a yellow-orange region emission. Large Stokes shift values were observed for all new derivatives and attributed to the ICT state and to the electron-substituent properties. The biomolecule-binding DNA and HSA-binding interactions were also investigated by experimental and theoretical methods.

中文翻译：

新型杂合苯并-2,1,3-噻二唑的合成，光物理与生物分子相互作用的研究

四个含有苯并-2,1,3-噻二唑，苯并呋喃和芳基戊二烯基部分的新杂合分子，分别命名为4,7-双（3-（芳基硒基）苯并呋喃-2-基）苯并[ c ] [1,2,5]噻二唑通过使用三氯异氰尿酸对4,7-双（（2-甲氧基苯基）乙炔基）苯并[ c ] [1,2,5]噻二唑1和二芳基二硒化物2进行亲电环化反应生成亲电的芳基硒基种类。化合物3a–d的光物理性质使用紫外可见吸收和发射荧光分析进行了研究。发射荧光分析显示橙黄色区域发射。对于所有新的导数，观察到较大的斯托克斯位移值，并且归因于ICT状态和电子取代基特性。还通过实验和理论方法研究了生物分子结合DNA和HSA结合相互作用。

更新日期：2020-02-17

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