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PreprintCC BYChemRxiv

Tunable Aza-BODIPY Photocatalysts for Near-Infrared Metallaphotoredox Atom Transfer Radical Polymerization

  • Jakub Piątkowski1
  • Paulina H. Marek-Urban2,3,4
  • Martyna Cybularczyk-Cecotka1
  • Magdalena Z. Wiloch-Szyborska5
  • Joanna Jankowska1
  • Yoichi Kobayashi3,4
  • Grzegorz Szczepaniak1
5 affiliations
  1. 1Faculty of Chemistry, University of Warsaw, Pasteura 1, Warsaw, Poland, 02-093
  2. 2Faculty of Chemistry, Warsaw University of Technology, Noakowskiego 3, Warsaw, Poland, 00-664
  3. 3College of Life Sciences
  4. 4Ritsumeikan University
  5. 5Institute of Physical Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, Warsaw, Poland, 01-224
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Abstract

The merger of photoredox and transition-metal catalysis has significantly advanced radical and redox transformations, yet its reliance on UV or visible light continues to limit applications in optically complex and spatially confined environments. Herein, we introduce a modular family of tetraaryl aza-boron-dipyrromethene (aza-BODIPY) organic photocatalysts (PCs) for near-infrared (NIR) metallaphotoredox atom transfer radical polymerization (ATRP). We systematically modulated peripheral electronics and core bromination, evaluating the dyes through quantum-chemical, electrochemical, and spectroscopic methods. This approach identified the key parameters governing catalytic performance: a delicate interplay between triplet-state accessibility, redox properties, and photostability. The optimized aza-BODIPY dye enables well-controlled ATRP of diverse acrylates and methacrylates at ultralow catalyst loadings, down to 5 ppm PC and 50 ppm copper complex. The system is further translated to open-air aqueous conditions, enabling rapid, high-throughput synthesis of water-soluble polymers in a 96-well plate format. Taking advantage of the enhanced penetration of NIR light, we demonstrate controlled polymerization through challenging physical barriers, including ex vivo tissue. Overall, this work defines design principles for far-red/NIR-absorbing aza-BODIPY PCs and expands the scope of NIR-mediated polymer synthesis to optically turbid, spatially restricted, and aqueous environments.

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Cite

BibTeXRIS
BibTeX
@misc{piatkowski2026tunable,
  title = {{Tunable Aza-BODIPY Photocatalysts for Near-Infrared Metallaphotoredox Atom Transfer Radical Polymerization}},
  author = {Jakub Piątkowski and Paulina H. Marek-Urban and Martyna Cybularczyk-Cecotka and Magdalena Z. Wiloch-Szyborska and Joanna Jankowska and Yoichi Kobayashi and Grzegorz Szczepaniak},
  howpublished = {ChemRxiv},
  year = {2026},
  month = oct,
  doi = {10.26434/chemrxiv.15010239/v1},
  url = {https://chemrxiv.org/doi/full/10.26434/chemrxiv.15010239/v1},
  note = {CC BY},
}
RIS
TY  - UNPB
TI  - Tunable Aza-BODIPY Photocatalysts for Near-Infrared Metallaphotoredox Atom Transfer Radical Polymerization
AU  - Jakub Piątkowski
AU  - Paulina H. Marek-Urban
AU  - Martyna Cybularczyk-Cecotka
AU  - Magdalena Z. Wiloch-Szyborska
AU  - Joanna Jankowska
AU  - Yoichi Kobayashi
AU  - Grzegorz Szczepaniak
PY  - 2026
DA  - 2026/10/11
PB  - ChemRxiv
DO  - 10.26434/chemrxiv.15010239/v1
UR  - https://chemrxiv.org/doi/full/10.26434/chemrxiv.15010239/v1
AB  - The merger of photoredox and transition-metal catalysis has significantly advanced radical and redox transformations, yet its reliance on UV or visible light continues to limit applications in optically complex and spatially confined environments. Herein, we introduce a modular family of tetraaryl aza-boron-dipyrromethene (aza-BODIPY) organic photocatalysts (PCs) for near-infrared (NIR) metallaphotoredox atom transfer radical polymerization (ATRP). We systematically modulated peripheral electronics and core bromination, evaluating the dyes through quantum-chemical, electrochemical, and spectroscopic methods. This approach identified the key parameters governing catalytic performance: a delicate interplay between triplet-state accessibility, redox properties, and photostability. The optimized aza-BODIPY dye enables well-controlled ATRP of diverse acrylates and methacrylates at ultralow catalyst loadings, down to 5 ppm PC and 50 ppm copper complex. The system is further translated to open-air aqueous conditions, enabling rapid, high-throughput synthesis of water-soluble polymers in a 96-well plate format. Taking advantage of the enhanced penetration of NIR light, we demonstrate controlled polymerization through challenging physical barriers, including ex vivo tissue. Overall, this work defines design principles for far-red/NIR-absorbing aza-BODIPY PCs and expands the scope of NIR-mediated polymer synthesis to optically turbid, spatially restricted, and aqueous environments.
ER  -