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Exploration of silicon phthalocyanines as viable photocatalysts for organic transformations
Journal of Photochemistry and Photobiology A: Chemistry ( IF 4.1 ) Pub Date : 2021-09-13 , DOI: 10.1016/j.jphotochem.2021.113547
Shelby D. Dickerson 1 , Pooja J. Ayare 1 , Aaron K. Vannucci 1 , Sheryl L. Wiskur 1
Affiliation  

Silicon phthalocyanines have been largely ignored as photocatalysts, despite their low energy excitation, long triplet lifetimes, and their ability to form singlet oxygen. By incorporating alkyl and silicon protecting groups as axial ligands on the silicon center, two silicon phthalocyanines have been generated with the goal of developing photocatalysts for organic synthesis. Using cyclic voltammetry and Stern Volmer quenching studies, we have shown silicon phthalocyanines are capable of electron transfer with appropriate substrates, including Hünig’s base. We have also successfully used these catalysts in a reductive quenching reaction where Hünig’s base served as a sacrificial electron donor in the reaction. In addition to being redox-active, our preliminary data also shows these compounds are capable of performing energy transfer reactions, by performing a reaction that utilizes singlet oxygen as a reactant under visible light conditions. This reaction, in combination with cyclic voltammetry studies, has also served as a model to understand how axial substitution on the silicon center seems to influence the photostability of these species.



中文翻译:

探索硅酞菁作为有机转化的可行光催化剂

硅酞菁作为光催化剂在很大程度上被忽视了,尽管它们的激发能量低、三线态寿命长,并且能够形成单线态氧。通过在硅中心结合烷基和硅保护基团作为轴向配体,已经生成了两种硅酞菁,其目标是开发用于有机合成的光催化剂。使用循环伏安法和 Stern Volmer 猝灭研究,我们已经证明硅酞菁能够与合适的底物(包括 Hünig 碱)进行电子转移。我们还成功地将这些催化剂用于还原淬火反应,其中 Hünig 碱在反应中用作牺牲电子供体。除了具有氧化还原活性外,我们的初步数据还表明这些化合物能够进行能量转移反应,通过在可见光条件下进行利用单线态氧作为反应物的反应。这种反应与循环伏安法研究相结合,还可以作为一个模型来了解硅中心上的轴向取代似乎如何影响这些物种的光稳定性。

更新日期:2021-09-28
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