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基于呋喃-吲哚-色酮的有机光催化剂用于烯醇醋酸酯的α-芳基化及在LED照射下的自由基聚合反应

Furan-Indole-Chromenone-Based Organic Photocatalyst for α-Arylation of Enol Acetate and Free Radical Polymerization Under LED Irradiation.

作者信息

Galibert-Guijarro Aurélien, Noon Adel, Toufaily Joumana, Hamieh Tayssir, Besson Eric, Gastaldi Stéphane, Lalevée Jacques, Feray Laurence

机构信息

Aix Marseille Univ, CNRS, ICR, 13013 Marseille, France.

Université de Haute-Alsace, CNRS, IS2M UMR 7361, F-68100 Mulhouse, France.

出版信息

Molecules. 2025 Jan 11;30(2):265. doi: 10.3390/molecules30020265.

Abstract

In this study we report on the efficiency of a furane-indole-chromenone-based organic derivative () as a photocatalyst in the α-arylation of enol acetate upon LED irradiation at 405 nm, and as a photoinitiator/photocatalyst in the free radical polymerization of an acrylate group in the presence of -(4--butylphenyl)iodonium hexafluorophosphate (Iod) as an additive, or in the presence of both Iod and ethyl-4-(dimethyl amino) benzoate (EDB) under LED irradiation at 365 nm. The photochemical properties of this new light-sensitive compound are described, and the wide redox window (3.27 eV) and the high excited-state potentials / (+2.64 V vs. SCE) and / (-2.41 V vs. SCE) offered by this photocatalyst are revealed. The chemical mechanisms that govern the radical chemistry are discussed by means of different techniques, including fluorescence-quenching experiments, UV-visible absorption and fluorescence spectroscopy, and cyclic voltammetry analysis.

摘要

在本研究中,我们报道了一种基于呋喃 - 吲哚 - 色原酮的有机衍生物()作为光催化剂在405 nm LED照射下用于乙酸烯醇酯α - 芳基化反应的效率,以及作为光引发剂/光催化剂在六氟磷酸 -(4 - 叔丁基苯基)碘鎓(Iod)作为添加剂存在下,或在Iod和4 - (二甲基氨基)苯甲酸乙酯(EDB)两者存在下于365 nm LED照射下用于丙烯酸酯基团自由基聚合反应的效率。描述了这种新型光敏化合物的光化学性质,并揭示了该光催化剂具有的宽氧化还原窗口(3.27 eV)以及高激发态电位/(相对于饱和甘汞电极(SCE)为 +2.64 V)和/(相对于SCE为 -2.41 V)。通过不同技术,包括荧光猝灭实验、紫外 - 可见吸收和荧光光谱以及循环伏安分析,讨论了控制自由基化学的化学机理。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/34f5/11767514/87293eb7abb8/molecules-30-00265-sch001.jpg

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