Visible-Light Amine Thioxanthone Derivatives as Photoredox Catalysts for Photopolymerization Processes,ACS Applied Polymer Materials

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Visible-Light Amine Thioxanthone Derivatives as Photoredox Catalysts for Photopolymerization Processes
ACS Applied Polymer Materials ( IF 4.4 ) Pub Date : 2021-10-25 , DOI: 10.1021/acsapm.1c00886
Emilia Hola ₁ , Paweł Fiedor _{1,

2} , Andrzej Dzienia ₃ , Joanna Ortyl _{1,

2,

4}

Affiliation

Herein, mono- and disubstituted thioxanthones have been synthesized and introduced as photosensitizers of iodonium salt for cationic and free-radical photopolymerization of epoxy and an acrylate monomer, respectively. Photoinitiation activity of these molecules was verified during photopolymerization processes performed upon exposure to visible LEDs of 420, 455, and 470 nm. The kinetics of the photopolymerization processes was followed using FT-IR spectroscopy. Moreover, the developed compounds were proposed as strongly reducing metal-free photoredox catalysts in organocatalyzed atom transfer radical polymerization (ATRP). Thioxanthone derivatives (with alkyl halide) efficiently activate the ATRP of methyl methacrylate using a visible LED as an irradiation source. The formed polymers in the ATRP process were characterized by SEC. Apart from studying the photopolymerization processes with the participation of obtained thioxanthones, absorption, fluorescence, as well as electrochemical properties of thioxanthone derivatives were investigated. Furthermore, the performance of studied compounds in 3D printing applications was also examined. The most important result of this study is the design and possible application of photosensitizers/photocatalysts for photopolymerization processes.

中文翻译：

可见光胺硫杂蒽酮衍生物作为光聚合过程的光氧化还原催化剂

在此，单取代和二取代的噻吨酮已被合成并作为碘鎓盐的光敏剂引入，分别用于环氧树脂和丙烯酸酯单体的阳离子和自由基光聚合。这些分子的光引发活性在暴露于 420、455 和 470 nm 的可见光 LED 后进行的光聚合过程中得到验证。使用 FT-IR 光谱跟踪光聚合过程的动力学。此外，所开发的化合物被提议作为有机催化原子转移自由基聚合（ATRP）中的强还原性无金属光氧化还原催化剂。使用可见光 LED 作为照射源，噻吨酮衍生物（含烷基卤化物）可有效激活甲基丙烯酸甲酯的 ATRP。ATRP 工艺中形成的聚合物通过 SEC 进行表征。除了研究得到噻吨酮参与的光聚合过程外，还研究了噻吨酮衍生物的吸收、荧光和电化学性质。此外，还检查了所研究化合物在 3D 打印应用中的性能。这项研究最重要的结果是光敏剂/光催化剂在光聚合过程中的设计和可能的应用。

更新日期：2021-11-12

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