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Development of porous organic polymers as metal-free photocatalysts for the aromatization of N-heterocycles

Maarten Debruyne (UGent) , Nathan Raeymackers (UGent) , Henk Vrielinck (UGent) , Sambhu Radhakrishnan, Eric Breynaert, Maxime Delaey (UGent) , Andreas Laemont (UGent) , Karen Leus (UGent) , Jonas Everaert (UGent) , Hannes Rijckaert (UGent) , et al.
(2024) CHEMCATCHEM. 16(7).
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Abstract
Porous organic polymers (POPs), and especially covalent triazine frameworks (CTFs), are being developed as the next generation of metal-free heterogeneous photocatalysts. However, many of the current synthetic routes to obtain these photoactive POPs require expensive monomers and rely on precious metal catalysts, thus hindering their widespread implementation. In this work, a range of POPs was synthesized from simple unfunctionalized aromatic building blocks, through Lewis acid-catalyzed polymerization. The obtained materials were applied, for the first time, as heterogeneous photocatalysts for the aromatization of N-heterocycles. With the use of the most active material, denoted as CTF-Pyr, which consists of photoactive pyrene and triazine moieties, a wide range of pyridines, dihydroquinoline-5-ones, tetrahydroacridine-1,8-diones and pyrazoles were obtained in excellent yields (70-99 %). Moreover, these reactions were carried out under very mild conditions using air and at room temperature, highlighting the potential of these materials as catalysts for green transformations.
Keywords
Covalent Triazine Frameworks, Heterogeneous Catalysis, N-Heterocycles, Oxidation, Photocatalysis, Porous Organic Polymers, TRIAZINE-BASED FRAMEWORKS, AEROBIC OXIDATIVE AROMATIZATION, SINGLET, OXYGEN GENERATION, HANTZSCH 1,4-DIHYDROPYRIDINES, MICROPOROUS POLYMERS, HYDROGEN EVOLUTION, ROOM-TEMPERATURE, GAS-STORAGE, WATER, AMINES

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Citation

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MLA
Debruyne, Maarten, et al. “Development of Porous Organic Polymers as Metal-Free Photocatalysts for the Aromatization of N-Heterocycles.” CHEMCATCHEM, vol. 16, no. 7, 2024, doi:10.1002/cctc.202301205.
APA
Debruyne, M., Raeymackers, N., Vrielinck, H., Radhakrishnan, S., Breynaert, E., Delaey, M., … Heugebaert, T. (2024). Development of porous organic polymers as metal-free photocatalysts for the aromatization of N-heterocycles. CHEMCATCHEM, 16(7). https://doi.org/10.1002/cctc.202301205
Chicago author-date
Debruyne, Maarten, Nathan Raeymackers, Henk Vrielinck, Sambhu Radhakrishnan, Eric Breynaert, Maxime Delaey, Andreas Laemont, et al. 2024. “Development of Porous Organic Polymers as Metal-Free Photocatalysts for the Aromatization of N-Heterocycles.” CHEMCATCHEM 16 (7). https://doi.org/10.1002/cctc.202301205.
Chicago author-date (all authors)
Debruyne, Maarten, Nathan Raeymackers, Henk Vrielinck, Sambhu Radhakrishnan, Eric Breynaert, Maxime Delaey, Andreas Laemont, Karen Leus, Jonas Everaert, Hannes Rijckaert, Dirk Poelman, Rino Morent, Nathalie De Geyter, Pascal Van Der Voort, Veronique Van Speybroeck, Christian Stevens, and Thomas Heugebaert. 2024. “Development of Porous Organic Polymers as Metal-Free Photocatalysts for the Aromatization of N-Heterocycles.” CHEMCATCHEM 16 (7). doi:10.1002/cctc.202301205.
Vancouver
1.
Debruyne M, Raeymackers N, Vrielinck H, Radhakrishnan S, Breynaert E, Delaey M, et al. Development of porous organic polymers as metal-free photocatalysts for the aromatization of N-heterocycles. CHEMCATCHEM. 2024;16(7).
IEEE
[1]
M. Debruyne et al., “Development of porous organic polymers as metal-free photocatalysts for the aromatization of N-heterocycles,” CHEMCATCHEM, vol. 16, no. 7, 2024.
@article{01HM4J0S257P0Y1JQDK0HHF4FJ,
  abstract     = {{Porous organic polymers (POPs), and especially covalent triazine

 frameworks (CTFs), are being developed as the next generation of

 metal-free heterogeneous photocatalysts. However, many of the current

 synthetic routes to obtain these photoactive POPs require expensive

 monomers and rely on precious metal catalysts, thus hindering their

 widespread implementation. In this work, a range of POPs was synthesized

 from simple unfunctionalized aromatic building blocks, through Lewis

 acid-catalyzed polymerization. The obtained materials were applied, for

 the first time, as heterogeneous photocatalysts for the aromatization of

 N-heterocycles. With the use of the most active material, denoted as

 CTF-Pyr, which consists of photoactive pyrene and triazine moieties, a

 wide range of pyridines, dihydroquinoline-5-ones,

 tetrahydroacridine-1,8-diones and pyrazoles were obtained in excellent

 yields (70-99 %). Moreover, these reactions were carried out under very

 mild conditions using air and at room temperature, highlighting the

 potential of these materials as catalysts for green transformations.}},
  articleno    = {{e202301205}},
  author       = {{Debruyne, Maarten and Raeymackers, Nathan and Vrielinck, Henk and Radhakrishnan, Sambhu and Breynaert, Eric and Delaey, Maxime and Laemont, Andreas and Leus, Karen and Everaert, Jonas and Rijckaert, Hannes and Poelman, Dirk and Morent, Rino and De Geyter, Nathalie and Van Der Voort, Pascal and Van Speybroeck, Veronique and Stevens, Christian and Heugebaert, Thomas}},
  issn         = {{1867-3880}},
  journal      = {{CHEMCATCHEM}},
  keywords     = {{Covalent Triazine Frameworks,Heterogeneous Catalysis,N-Heterocycles,Oxidation,Photocatalysis,Porous Organic Polymers,TRIAZINE-BASED FRAMEWORKS,AEROBIC OXIDATIVE AROMATIZATION,SINGLET,OXYGEN GENERATION,HANTZSCH 1,4-DIHYDROPYRIDINES,MICROPOROUS POLYMERS,HYDROGEN EVOLUTION,ROOM-TEMPERATURE,GAS-STORAGE,WATER,AMINES}},
  language     = {{eng}},
  number       = {{7}},
  pages        = {{15}},
  title        = {{Development of porous organic polymers as metal-free photocatalysts for the aromatization of N-heterocycles}},
  url          = {{http://doi.org/10.1002/cctc.202301205}},
  volume       = {{16}},
  year         = {{2024}},
}
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