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Engineering of phenylpyridine- and bipyridine-based covalent organic frameworks for photocatalytic tandem aerobic oxidation/povarov cyclization

Maarten Debruyne (UGent) , Sander Borgmans (UGent) , Sambhu Radhakrishnan, Eric Breynaert, Henk Vrielinck (UGent) , Karen Leus (UGent) , Andreas Laemont (UGent) , Juul De Vos (UGent) , Kuber Singh Rawat (UGent) , Siebe Vanlommel (UGent) , et al.
(2023) ACS APPLIED MATERIALS & INTERFACES. 15(29). p.35092-35106
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Abstract
Covalentorganic frameworks (COFs) are emerging as a new classof photoactive organic semiconductors, which possess crystalline orderedstructures and high surface areas. COFs can be tailor-made towardspecific (photocatalytic) applications, and the size and positionof their band gaps can be tuned by the choice of building blocks andlinkages. However, many types of building blocks are still unexploredas photocatalytic moieties and the scope of reactions photocatalyzedby COFs remains quite limited. In this work, we report the synthesisand application of two bipyridine- or phenylpyridine-based COFs: TpBpyCOF and TpPpyCOF. Due to their good photocatalyticproperties, both materials were applied as metal-free photocatalystsfor the tandem aerobic oxidation/Povarov cyclization and & alpha;-oxidationof N-aryl glycine derivatives, with the bipyridine-based TpBpyCOF exhibiting the highest activity. By expanding therange of reactions that can be photocatalyzed by COFs, this work pavesthe way toward the more widespread application of COFs as metal-freeheterogeneous photocatalysts as a convenient alternative for commonlyused homogeneous (metal-based) photocatalysts.
Keywords
covalent organic frameworks, photocatalysis, oxidation, Povarov, reaction, heterogeneous catalysis, GLYCINE DERIVATIVES, SINGLET-OXYGEN, C-SP3-H FUNCTIONALIZATION, HYDROGEN, EVOLUTION, WATER, EFFICIENT, GENERATION, MECHANISM, DESIGN, AMINES

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Citation

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MLA
Debruyne, Maarten, et al. “Engineering of Phenylpyridine- and Bipyridine-Based Covalent Organic Frameworks for Photocatalytic Tandem Aerobic Oxidation/Povarov Cyclization.” ACS APPLIED MATERIALS & INTERFACES, vol. 15, no. 29, 2023, pp. 35092–106, doi:10.1021/acsami.3c07036.
APA
Debruyne, M., Borgmans, S., Radhakrishnan, S., Breynaert, E., Vrielinck, H., Leus, K., … Stevens, C. (2023). Engineering of phenylpyridine- and bipyridine-based covalent organic frameworks for photocatalytic tandem aerobic oxidation/povarov cyclization. ACS APPLIED MATERIALS & INTERFACES, 15(29), 35092–35106. https://doi.org/10.1021/acsami.3c07036
Chicago author-date
Debruyne, Maarten, Sander Borgmans, Sambhu Radhakrishnan, Eric Breynaert, Henk Vrielinck, Karen Leus, Andreas Laemont, et al. 2023. “Engineering of Phenylpyridine- and Bipyridine-Based Covalent Organic Frameworks for Photocatalytic Tandem Aerobic Oxidation/Povarov Cyclization.” ACS APPLIED MATERIALS & INTERFACES 15 (29): 35092–106. https://doi.org/10.1021/acsami.3c07036.
Chicago author-date (all authors)
Debruyne, Maarten, Sander Borgmans, Sambhu Radhakrishnan, Eric Breynaert, Henk Vrielinck, Karen Leus, Andreas Laemont, Juul De Vos, Kuber Singh Rawat, Siebe Vanlommel, Hannes Rijckaert, Hadi Salemi, Jonas Everaert, Florence Vanden Bussche, Dirk Poelman, Rino Morent, Nathalie De Geyter, Pascal Van Der Voort, Veronique Van Speybroeck, and Christian Stevens. 2023. “Engineering of Phenylpyridine- and Bipyridine-Based Covalent Organic Frameworks for Photocatalytic Tandem Aerobic Oxidation/Povarov Cyclization.” ACS APPLIED MATERIALS & INTERFACES 15 (29): 35092–35106. doi:10.1021/acsami.3c07036.
Vancouver
1.
Debruyne M, Borgmans S, Radhakrishnan S, Breynaert E, Vrielinck H, Leus K, et al. Engineering of phenylpyridine- and bipyridine-based covalent organic frameworks for photocatalytic tandem aerobic oxidation/povarov cyclization. ACS APPLIED MATERIALS & INTERFACES. 2023;15(29):35092–106.
IEEE
[1]
M. Debruyne et al., “Engineering of phenylpyridine- and bipyridine-based covalent organic frameworks for photocatalytic tandem aerobic oxidation/povarov cyclization,” ACS APPLIED MATERIALS & INTERFACES, vol. 15, no. 29, pp. 35092–35106, 2023.
@article{01H96JS3GP8WJBC5PAMDSR9HPA,
  abstract     = {{Covalentorganic frameworks (COFs) are emerging as a new classof

 photoactive organic semiconductors, which possess crystalline

 orderedstructures and high surface areas. COFs can be tailor-made

 towardspecific (photocatalytic) applications, and the size and

 positionof their band gaps can be tuned by the choice of building blocks

 andlinkages. However, many types of building blocks are still

 unexploredas photocatalytic moieties and the scope of reactions

 photocatalyzedby COFs remains quite limited. In this work, we report the

 synthesisand application of two bipyridine- or phenylpyridine-based

 COFs: TpBpyCOF and TpPpyCOF. Due to their good photocatalyticproperties,

 both materials were applied as metal-free photocatalystsfor the tandem

 aerobic oxidation/Povarov cyclization and & alpha;-oxidationof N-aryl

 glycine derivatives, with the bipyridine-based TpBpyCOF exhibiting the

 highest activity. By expanding therange of reactions that can be

 photocatalyzed by COFs, this work pavesthe way toward the more

 widespread application of COFs as metal-freeheterogeneous photocatalysts

 as a convenient alternative for commonlyused homogeneous (metal-based)

 photocatalysts.}},
  author       = {{Debruyne, Maarten and Borgmans, Sander and Radhakrishnan, Sambhu and Breynaert, Eric and Vrielinck, Henk and Leus, Karen and Laemont, Andreas and De Vos, Juul and Singh Rawat, Kuber and Vanlommel, Siebe and Rijckaert, Hannes and Salemi, Hadi and Everaert, Jonas and Vanden Bussche, Florence and Poelman, Dirk and Morent, Rino and De Geyter, Nathalie and Van Der Voort, Pascal and Van Speybroeck, Veronique and Stevens, Christian}},
  issn         = {{1944-8244}},
  journal      = {{ACS APPLIED MATERIALS & INTERFACES}},
  keywords     = {{covalent organic frameworks,photocatalysis,oxidation,Povarov,reaction,heterogeneous catalysis,GLYCINE DERIVATIVES,SINGLET-OXYGEN,C-SP3-H FUNCTIONALIZATION,HYDROGEN,EVOLUTION,WATER,EFFICIENT,GENERATION,MECHANISM,DESIGN,AMINES}},
  language     = {{eng}},
  number       = {{29}},
  pages        = {{35092--35106}},
  title        = {{Engineering of phenylpyridine- and bipyridine-based covalent organic frameworks for photocatalytic tandem aerobic oxidation/povarov cyclization}},
  url          = {{http://doi.org/10.1021/acsami.3c07036}},
  volume       = {{15}},
  year         = {{2023}},
}
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