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Issue 12, 2018
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Mechanistic insights into two-photon-driven photocatalysis in organic synthesis

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Abstract

A mechanism based on the sequential absorption of two photons by the components of a redox couple has been recently proposed for catalysis of the energetically demanding reduction of aryl halides. Here, we analyze the suggested photochemical mechanism of this reaction, which employs perylenediimide (PDI) as a photocatalyst, on the basis of spectroscopic, electrochemical and electron paramagnetic resonance data. Our results indicate that the photoexcited PDI radical anion (*PDI˙) cannot play the role of a photosensitizer in the aforementioned process. Instead, the reduction of 4′-bromoacetophenone likely involves *PDI˙ decomposition products. The extremely short lifetime of the photoexcited transient species, as *PDI˙, is a major general limitation for photocatalytic schemes based on sequential two-photon excitation. In order to better understand the potential of such schemes, we discuss them in the context of the Z-scheme in natural photosynthesis.

Graphical abstract: Mechanistic insights into two-photon-driven photocatalysis in organic synthesis

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Publication details

The article was received on 29 Nov 2017, accepted on 14 Feb 2018 and first published on 08 Mar 2018


Article type: Paper
DOI: 10.1039/C7CP08011E
Citation: Phys. Chem. Chem. Phys., 2018,20, 8071-8076
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    Mechanistic insights into two-photon-driven photocatalysis in organic synthesis

    M. Marchini, A. Gualandi, L. Mengozzi, P. Franchi, M. Lucarini, P. G. Cozzi, V. Balzani and P. Ceroni, Phys. Chem. Chem. Phys., 2018, 20, 8071
    DOI: 10.1039/C7CP08011E

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