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Red light-driven electron sacrificial agents-free photoreduction of inert aryl halides via triplet-triplet annihilation

Author

Listed:
  • Le Zeng

    (University of Massachusetts Chan Medical School
    Nankai University)

  • Ling Huang

    (University of Massachusetts Chan Medical School
    Nankai University)

  • Wenhai Lin

    (University of Massachusetts Chan Medical School)

  • Lin-Han Jiang

    (Nankai University)

  • Gang Han

    (University of Massachusetts Chan Medical School)

Abstract

Selective photoactivation of inert aryl halides is a fundamental challenge in organic synthesis. Specially, the long-wavelength red light is more desirable than the widely-applied blue light as the excitation source for photoredox catalysis, due to its superior penetration depth. However, the long-wavelength red light-driven photoactivation of inert aryl halides remains a challenge, mainly because of the low energy of the single long-wavelength red photon. Herein, we report the photoreduction of aryl bromides/chlorides with 656 nm LED via triplet-triplet annihilation (TTA) strategy. This method is based on our discovery that the commonly used chromophore of perylene can serve as an efficient and metal-free photocatalyst to enable the photoreduction of inert aryl halides without the conventional need for electronic sacrificial agents. By introducing a red light-absorbing photosensitizer to this perylene system, we accomplish the long-wavelength red light-driven photoreduction of aryl halides via sensitized TTA mechanism. Moreover, the performance of such a TTA-mediated photoreduction can be significantly enhanced when restricting the rotation freedom of phenyl moiety for perylene derivatives to suppress their triplet nonradiative transition, in both small and large-scale reaction settings.

Suggested Citation

  • 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.
  • Handle: RePEc:nat:natcom:v:14:y:2023:i:1:d:10.1038_s41467-023-36679-7
    DOI: 10.1038/s41467-023-36679-7
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    References listed on IDEAS

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    1. Ian A. MacKenzie & Leifeng Wang & Nicholas P. R. Onuska & Olivia F. Williams & Khadiza Begam & Andrew M. Moran & Barry D. Dunietz & David A. Nicewicz, 2020. "Discovery and characterization of an acridine radical photoreductant," Nature, Nature, vol. 580(7801), pages 76-80, April.
    2. Samuel N. Sanders & Tracy H. Schloemer & Mahesh K. Gangishetty & Daniel Anderson & Michael Seitz & Arynn O. Gallegos & R. Christopher Stokes & Daniel N. Congreve, 2022. "Triplet fusion upconversion nanocapsules for volumetric 3D printing," Nature, Nature, vol. 604(7906), pages 474-478, April.
    3. Benjamin D. Ravetz & Andrew B. Pun & Emily M. Churchill & Daniel N. Congreve & Tomislav Rovis & Luis M. Campos, 2019. "Author Correction: Photoredox catalysis using infrared light via triplet fusion upconversion," Nature, Nature, vol. 570(7759), pages 24-24, June.
    4. Mattia Silvi & Paolo Melchiorre, 2018. "Enhancing the potential of enantioselective organocatalysis with light," Nature, Nature, vol. 554(7690), pages 41-49, February.
    5. 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.
    6. Ming Xu & Xianmei Zou & Qianqian Su & Wei Yuan & Cong Cao & Qiuhong Wang & Xingjun Zhu & Wei Feng & Fuyou Li, 2018. "Ratiometric nanothermometer in vivo based on triplet sensitized upconversion," Nature Communications, Nature, vol. 9(1), pages 1-7, December.
    7. Haohua Huo & Xiaodong Shen & Chuanyong Wang & Lilu Zhang & Philipp Röse & Liang-An Chen & Klaus Harms & Michael Marsch & Gerhard Hilt & Eric Meggers, 2014. "Asymmetric photoredox transition-metal catalysis activated by visible light," Nature, Nature, vol. 515(7525), pages 100-103, November.
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