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Photoredox catalysis using infrared light via triplet fusion upconversion

Author

Listed:
  • 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)

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.

Suggested Citation

  • Benjamin D. Ravetz & Andrew B. Pun & Emily M. Churchill & Daniel N. Congreve & Tomislav Rovis & Luis M. Campos, 2019. "Photoredox catalysis using infrared light via triplet fusion upconversion," Nature, Nature, vol. 565(7739), pages 343-346, January.
  • Handle: RePEc:nat:nature:v:565:y:2019:i:7739:d:10.1038_s41586-018-0835-2
    DOI: 10.1038/s41586-018-0835-2
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    Citations

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    Cited by:

    1. Yunxiao Zhang & Yizhi Zhang & Chen Ye & Xiaotian Qi & Li-Zhu Wu & Xiao Shen, 2022. "Cascade cyclization of alkene-tethered acylsilanes and allylic sulfones enabled by unproductive energy transfer photocatalysis," Nature Communications, Nature, vol. 13(1), pages 1-11, December.
    2. Guiying He & Emily M. Churchill & Kaia R. Parenti & Jocelyn Zhang & Pournima Narayanan & Faridah Namata & Michael Malkoch & Daniel N. Congreve & Angelo Cacciuto & Matthew Y. Sfeir & Luis M. Campos, 2023. "Promoting multiexciton interactions in singlet fission and triplet fusion upconversion dendrimers," Nature Communications, Nature, vol. 14(1), pages 1-10, December.
    3. Xinyu Wang & Fangwei Ding & Tao Jia & Feng Li & Xiping Ding & Ruibin Deng & Kaifeng Lin & Yulin Yang & Wenzhi Wu & Debin Xia & Guanying Chen, 2024. "Molecular near-infrared triplet-triplet annihilation upconversion with eigen oxygen immunity," Nature Communications, Nature, vol. 15(1), pages 1-12, December.
    4. Le Zeng & Ling Huang & Wenhai Lin & Lin-Han Jiang & Gang Han, 2023. "Red light-driven electron sacrificial agents-free photoreduction of inert aryl halides via triplet-triplet annihilation," Nature Communications, Nature, vol. 14(1), pages 1-9, December.
    5. J. Perego & Charl X. Bezuidenhout & I. Villa & F. Cova & R. Crapanzano & I. Frank & F. Pagano & N. Kratochwill & E. Auffray & S. Bracco & A. Vedda & C. Dujardin & P. E. Sozzani & F. Meinardi & A. Como, 2022. "Highly luminescent scintillating hetero-ligand MOF nanocrystals with engineered Stokes shift for photonic applications," Nature Communications, Nature, vol. 13(1), pages 1-10, December.
    6. Guanqun Han & Guodong Li & Jie Huang & Chuang Han & Claudia Turro & Yujie Sun, 2022. "Two-photon-absorbing ruthenium complexes enable near infrared light-driven photocatalysis," Nature Communications, Nature, vol. 13(1), pages 1-10, December.
    7. Hailei Zhang & Boyan Tang & Bo Zhang & Kai Huang & Shanshan Li & Yuangong Zhang & Haisong Zhang & Libin Bai & Yonggang Wu & Yongqiang Cheng & Yanmin Yang & Gang Han, 2024. "X-ray-activated polymerization expanding the frontiers of deep-tissue hydrogel formation," Nature Communications, Nature, vol. 15(1), pages 1-11, December.
    8. Le Zeng & Ling Huang & Zhi Huang & Tomoyasu Mani & Kai Huang & Chunying Duan & Gang Han, 2024. "Long wavelength near-infrared and red light-driven consecutive photo-induced electron transfer for highly effective photoredox catalysis," Nature Communications, Nature, vol. 15(1), pages 1-10, December.

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