接受者
电化学
共轭体系
Stille反应
带隙
分子
激发态
化学
吸收光谱法
摩尔吸收率
吸收(声学)
光化学
材料科学
物理化学
聚合物
有机化学
光电子学
物理
电极
光学
复合材料
量子力学
核物理学
凝聚态物理
作者
Nikita S. Gudim,Ekaterina A. Knyazeva,Ludmila V. Mikhalchenko,Ivan S. Golovanov,В. В. Попов,Natalia V. Obruchnikova,Олег А. Ракитин
出处
期刊:Molecules
[MDPI AG]
日期:2021-08-14
卷期号:26 (16): 4931-4931
被引量:20
标识
DOI:10.3390/molecules26164931
摘要
This paper presents an improved synthesis of 4,7-dibromobenzo[d][1,2,3]thiadiazole from commercially available reagents. According to quantum-mechanical calculations, benzo[d][1,2,3]thiadiazole (isoBTD) has higher values of ELUMO and energy band gap (Eg), which indicates high electron conductivity, occurring due to the high stability of the molecule in the excited state. We studied the cross-coupling reactions of this dibromide and found that the highest yields of π-spacer–acceptor–π-spacer type compounds were obtained by means of the Stille reaction. Therefore, 6 new structures of this type have been synthesized. A detailed study of the optical and electrochemical properties of the obtained π-spacer–acceptor–π-spacer type compounds in comparison with isomeric structures based on benzo[c][1,2,5]thiadiazole (BTD) showed a red shift of absorption maxima with lower absorptive and luminescent capacity. However, the addition of the 2,2′-bithiophene fragment as a π-spacer resulted in an unexpected increase of the extinction coefficient in the UV/vis spectra along with a blue shift of both absorption maxima for the isoBTD-based compound as compared to the BTD-based compound. Thus, a thorough selection of components in the designing of appropriate compounds with benzo[d][1,2,3]thiadiazole as an internal acceptor can lead to promising photovoltaic materials.
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