Synthesis of Triazolo[c]coumarins and Differences in the Fluorescence Properties of Their Isomers
Synthesis of Triazolo[c]coumarins and Differences in the Fluorescence Properties of Their Isomers
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三唑并[c]香豆素的合成及其异构体荧光性质的差异
DOI：
10.1002/ajoc.202300013
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发表时间：
2023
影响因子：
2.7
通讯作者：
Itoh Toshimasa
中科院分区：
文献类型：
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作者：
Sekine Miyu;Ishida Hiroaki;Itoh Toshimasa
尽管3，4-稠合三环香豆素结构简单，但其荧光性质尚未得到广泛研究。采用Huisgen环加成反应合成了三唑并[c]香豆素类化合物，并对其荧光性质进行了研究。发现Huisgen环加成在无溶剂条件下加热时以优异的产率进行。如通常所知，荧光随着7位上的供电子基团的增加而增强。7-NEt 2-三唑并[c]香豆素衍生物在非质子极性有机溶剂中表现出良好的荧光性能，且相对荧光量子产率较高。结果表明，三唑并[c]香豆素类化合物的荧光性质与其位置异构体有关。用密度泛函理论（DFT）和含时密度泛函理论（TD-DFT）计算了三唑的分子轨道，发现电子分布几乎没有扩展到烷基侧链.该结果表明，即使在三唑上引入各种取代基，荧光性质的趋势也与本结果相似。
Despite the simple structures of 3,4‐fused tricyclo coumarins, their fluorescence properties have not been studied extensively. We have synthesized triazolo[c]coumarins using Huisgen cycloaddition and investigated their fluorescence properties. The Huisgen cycloaddition was found to proceed in excellent yields when subjected to heating under solvent‐free conditions. As is generally known, fluorescence is enhanced with an increase in the electron‐donating group at the 7‐position. The 7‐NEt2‐triazolo[c]coumarin derivatives showed useful fluorescence, and their relative fluorescence quantum yields in aprotic polar organic solvents were high. It revealed that fluorescence properties of triazolo[c]coumarins depended on the regio isomer. The electron distribution was hardly extended to alkyl side chain on triazole from the molecular orbital calculation by density functional theory (DFT) and time‐dependent DFT (TD‐DFT). This result suggests that the trend of fluorescence properties is similar to the present result even when various substituents are introduced on triazole.