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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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Supplementary files

Article information


Submitted
29 Nov 2017
Accepted
14 Feb 2018
First published
08 Mar 2018

Phys. Chem. Chem. Phys., 2018,20, 8071-8076
Article type
Paper

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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