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Ligand electronic fine-tuning and its repercussion on the photocatalytic activity and mechanistic pathways of the copper-photocatalysed aza-Henry Reaction

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Author(s)

Chenfei Li, Robert Dickson, Nils Rockstroh, Jabor Rabeah, David B. Cordes, Alexandra M. Z. Slawin, Paul Hünemörder, Anke Spannenberg, Michael Buehl, Esteban Mejía, Eli Zysman-Colman, Paul C J Kamer

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Abstract

A family of six structurally related heteroleptic copper(I) complexes of the form of [Cu(N^N)(P^P)]+ bearing a 2,9-dimethyl-1,10-phenanthroline diimine (N^N) ligand and a series of electronically tunable xantphos (P^P) ligands have been synthesized and their optoelectronic properties characterized. The reactivity of these complexes in the copper-photocatalyzed Aza-Henry reaction of N-Phenyltetrahydroisoquinoline was evaluated, while the related excited state kinetics were comprehensively studied. By subtlety changing the electron-donating properties of the P^P ligands with neglegible structural differences, we could tailor the photoredox properties and relate it to their reactivity. Moreover, depending on the exited-state redox potential of the catalysts, the preferred mechanism can shift between reductive quenching, energy transfer and oxidative quenching pathways. A combined study of structural modulation of copper(I) photocatalysts, optoelectronic properties and photocatalytic reactivity resulted in a clearer understanding of both the rational design of the photocatalyst and the complexity of competing photoinduced electron and energy transfer mechanisms.
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Original languageEnglish
Number of pages12
JournalCatalysis Science & Technology
VolumeAdvance Article
Early online date18 Sep 2020
DOIs
Publication statusE-pub ahead of print - 18 Sep 2020

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