双（二噻吩）取代苯并[1,2-d:4,3-d ']二噻唑的光物理和电化学性质

IF 1.7 4区化学 Q3 CHEMISTRY, MULTIDISCIPLINARY

Russian Chemical Bulletin Pub Date : 2025-05-15 DOI:10.1007/s11172-025-4591-9

A. S. Kostyuchenko, E. B. Uliankin, T. Yu. Zheleznova, A. L. Shatsauskas, V. Yu. Shuvalov, A. S. Fisyuk

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引用次数: 0

摘要

在氯胺的存在下，将相应的N，N ' -（苯并[c][1,2,5]噻二唑-4,7-二基）和N，N ' -（2h -苯并[d][1,2,3]三唑-4,7-二基）二硫酰胺进行光化学环化，合成了双（二噻吩）取代苯并[1,2-d:4,3-d]二噻吩]二噻唑。分析了这种环化反应的机理。研究了中心杂环结构对合成化合物的电化学、电子和光物理性质的影响。致光孔的THF溶液的量子产率在0.16-0.62之间。中心杂环的吸电子效应的增加稳定了自由基阴离子，降低了还原电位，eonsett和带隙宽度。

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Photophysical and electrochemical properties of bis(dithiophene)-substituted benzo[1,2-d:4,3-d′]dithiazoles

Bis(dithiophene)-substituted benzo[1,2-d:4,3-d′]dithiazoles were synthesized by a photochemical cyclization of corresponding N,N′-(benzo[c][1,2,5]thiadiazole-4,7-diyl)- and N,N′-(2H-benzo[d][1,2,3]triazole-4,7-diyl)dithioamides in the presence of chloranil. The mechanism of this cyclization was analyzed. The influence of the structure of the central heterocycle on the electrochemical, electronic, and photophysical properties of the synthesized compounds was studied. Quantum yields for THF solutions of the luminophpores are in the range 0.16–0.62. An increase in the electron-withdrawing effects of the central heterocycle stabilizes the radical anion and reduces the reduction potential, E_onset^red, and the width of the band gap.

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来源期刊

Russian Chemical Bulletin 化学-化学综合

CiteScore

2.70

自引率

47.10%

发文量

257

审稿时长

3-8 weeks

期刊介绍： Publishing nearly 500 original articles a year, by leading Scientists from Russia and throughout the world, Russian Chemical Bulletin is a prominent international journal. The coverage of the journal spans practically all areas of fundamental chemical research and is presented in five sections: General and Inorganic Chemistry; Physical Chemistry; Organic Chemistry; Organometallic Chemistry; Chemistry of Natural Compounds and Bioorganic Chemistry.