Development of a tethered palladium-BODIPY dual catalyst for enhanced photo- and thermally activated catalysis, and for promoting sequential reactivity

Danfeng Wang, Nicholas S. D. Solomon, Indrek Pernik, Barbara A. Messerle*, Sinead T. Keaveney

*Corresponding author for this work

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

In recent years there has been a growing interest in merging different types of catalysis to create new multistep catalytic processes. However, the majority of reported dual catalysis strategies use a mixture of individual catalysts, with limited reports of dual catalysis reactions where the different catalysts are combined in a single compound. This work reports the synthesis of a tethered palladium-BODIPY dual catalyst to enable increased synergistic interactions between the catalytic centres. Detailed analysis, including single crystal X-ray crystallography, absorption, fluorescence, and phosphorescence measurements, and kinetic analyses to determine singlet oxygen quantum yields, confirm that chemical tethering results in a significant increase in the photocatalytic potential of the palladium-BODIPY dual catalyst, relative to the parent BODIPY chromophore. Interestingly, the palladium-BODIPY complex also exhibited rare long-lived room temperature phosphorescence. Catalytic applications of the palladium-BODIPY dual catalyst indicate that chemical tethering increases the reactivity of the catalytic centres for both photocatalytic oxidation of thioanisole and palladium catalysed Suzuki-Miyaura cross coupling, highlighting that enhancements in both photo and thermally activated catalysis can be achieved on chemical tethering. In addition, the dual catalytic potential of the palladium-BODIPY catalyst was demonstrated using a representative sequential photocatalytic oxidation-cross coupling reaction.

Original languageEnglish
JournalAustralian Journal of Chemistry
DOIs
Publication statusE-pub ahead of print - 24 Apr 2020

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