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

Journal Article


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.

Publication Date


  • 2020

Citation


  • Wang, D., Solomon, N. S. D., Pernik, I., Messerle, B. A., & Keaveney, S. T. (2020). Development of a tethered Palladium-BODIPY dual catalyst for enhanced photo- And thermally activated catalysis, and for promoting sequential reactivity. Australian Journal of Chemistry, 73(10), 979-986. doi:10.1071/CH19569

Scopus Eid


  • 2-s2.0-85084134730

Start Page


  • 979

End Page


  • 986

Volume


  • 73

Issue


  • 10

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.

Publication Date


  • 2020

Citation


  • Wang, D., Solomon, N. S. D., Pernik, I., Messerle, B. A., & Keaveney, S. T. (2020). Development of a tethered Palladium-BODIPY dual catalyst for enhanced photo- And thermally activated catalysis, and for promoting sequential reactivity. Australian Journal of Chemistry, 73(10), 979-986. doi:10.1071/CH19569

Scopus Eid


  • 2-s2.0-85084134730

Start Page


  • 979

End Page


  • 986

Volume


  • 73

Issue


  • 10