Photoredox catalysis using infrared light via triplet fusion upconversion

Benjamin D. Ravetz, Andrew B. Pun, Emily M. Churchill, Daniel N. Congreve (), Tomislav Rovis () and Luis M. Campos ()
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Benjamin D. Ravetz: Columbia University
Andrew B. Pun: Columbia University
Emily M. Churchill: Columbia University
Daniel N. Congreve: Rowland Institute at Harvard University
Tomislav Rovis: Columbia University
Luis M. Campos: Columbia University

Nature, 2019, vol. 565, issue 7739, 343-346

Abstract: Abstract Recent advances in photoredox catalysis have made it possible to achieve various challenging synthetic transformations, polymerizations and surface modifications1–3. All of these reactions require ultraviolet- or visible-light stimuli; however, the use of visible-light irradiation has intrinsic challenges. For example, the penetration of visible light through most reaction media is very low, leading to problems in large-scale reactions. Moreover, reactants can compete with photocatalysts for the absorption of incident light, limiting the scope of the reactions. These problems can be overcome by the use of near-infrared light, which has a much higher penetration depth through various media, notably biological tissue4. Here we demonstrate various photoredox transformations under infrared radiation by utilizing the photophysical process of triplet fusion upconversion, a mechanism by which two low-energy photons are converted into a higher-energy photon. We show that this is a general strategy applicable to a wide range of photoredox reactions. We tune the upconversion components to adjust the output light, accessing both orange light and blue light from low-energy infrared light, by pairwise manipulation of the sensitizer and annihilator. We further demonstrate that the annihilator itself can be used as a photocatalyst, thus simplifying the reaction. This approach enables catalysis of high-energy transformations through several opaque barriers using low-energy infrared light.

Date: 2019
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DOI: 10.1038/s41586-018-0835-2

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