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Acridine‐Functionalized Covalent Organic Frameworks (COFs) as Photocatalysts for Metallaphotocatalytic C−N Cross‐Coupling

Covalent organic frameworks (COFs) are structurally tuneable, porous and crystalline polymers constructed through the covalent attachment of small organic building blocks as elementary units. Using the myriad of such building blocks, a broad spectrum of functionalities has been applied for COF synth...

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Autores principales: Traxler, Michael, Gisbertz, Sebastian, Pachfule, Pradip, Schmidt, Johannes, Roeser, Jérôme, Reischauer, Susanne, Rabeah, Jabor, Pieber, Bartholomäus, Thomas, Arne
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9400916/
https://www.ncbi.nlm.nih.gov/pubmed/35188714
http://dx.doi.org/10.1002/anie.202117738
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author Traxler, Michael
Gisbertz, Sebastian
Pachfule, Pradip
Schmidt, Johannes
Roeser, Jérôme
Reischauer, Susanne
Rabeah, Jabor
Pieber, Bartholomäus
Thomas, Arne
author_facet Traxler, Michael
Gisbertz, Sebastian
Pachfule, Pradip
Schmidt, Johannes
Roeser, Jérôme
Reischauer, Susanne
Rabeah, Jabor
Pieber, Bartholomäus
Thomas, Arne
author_sort Traxler, Michael
collection PubMed
description Covalent organic frameworks (COFs) are structurally tuneable, porous and crystalline polymers constructed through the covalent attachment of small organic building blocks as elementary units. Using the myriad of such building blocks, a broad spectrum of functionalities has been applied for COF syntheses for broad applications, including heterogeneous catalysis. Herein, we report the synthesis of a new family of porous and crystalline COFs using a novel acridine linker and benzene‐1,3,5‐tricarbaldehyde derivatives bearing a variable number of hydroxy groups. With the broad absorption in the visible light region, the COFs were applied as photocatalysts in metallaphotocatalytic C−N cross‐coupling. The fully β‐ketoenamine linked COF showed the highest activity, due to the increased charge separation upon irradiation. The COF showed good to excellent yields for several aryl bromides, good recyclability and even catalyzed the organic transformation in presence of green light as energy source.
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spelling pubmed-94009162022-08-26 Acridine‐Functionalized Covalent Organic Frameworks (COFs) as Photocatalysts for Metallaphotocatalytic C−N Cross‐Coupling Traxler, Michael Gisbertz, Sebastian Pachfule, Pradip Schmidt, Johannes Roeser, Jérôme Reischauer, Susanne Rabeah, Jabor Pieber, Bartholomäus Thomas, Arne Angew Chem Int Ed Engl Research Articles Covalent organic frameworks (COFs) are structurally tuneable, porous and crystalline polymers constructed through the covalent attachment of small organic building blocks as elementary units. Using the myriad of such building blocks, a broad spectrum of functionalities has been applied for COF syntheses for broad applications, including heterogeneous catalysis. Herein, we report the synthesis of a new family of porous and crystalline COFs using a novel acridine linker and benzene‐1,3,5‐tricarbaldehyde derivatives bearing a variable number of hydroxy groups. With the broad absorption in the visible light region, the COFs were applied as photocatalysts in metallaphotocatalytic C−N cross‐coupling. The fully β‐ketoenamine linked COF showed the highest activity, due to the increased charge separation upon irradiation. The COF showed good to excellent yields for several aryl bromides, good recyclability and even catalyzed the organic transformation in presence of green light as energy source. John Wiley and Sons Inc. 2022-03-23 2022-05-16 /pmc/articles/PMC9400916/ /pubmed/35188714 http://dx.doi.org/10.1002/anie.202117738 Text en © 2022 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH https://creativecommons.org/licenses/by/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Research Articles
Traxler, Michael
Gisbertz, Sebastian
Pachfule, Pradip
Schmidt, Johannes
Roeser, Jérôme
Reischauer, Susanne
Rabeah, Jabor
Pieber, Bartholomäus
Thomas, Arne
Acridine‐Functionalized Covalent Organic Frameworks (COFs) as Photocatalysts for Metallaphotocatalytic C−N Cross‐Coupling
title Acridine‐Functionalized Covalent Organic Frameworks (COFs) as Photocatalysts for Metallaphotocatalytic C−N Cross‐Coupling
title_full Acridine‐Functionalized Covalent Organic Frameworks (COFs) as Photocatalysts for Metallaphotocatalytic C−N Cross‐Coupling
title_fullStr Acridine‐Functionalized Covalent Organic Frameworks (COFs) as Photocatalysts for Metallaphotocatalytic C−N Cross‐Coupling
title_full_unstemmed Acridine‐Functionalized Covalent Organic Frameworks (COFs) as Photocatalysts for Metallaphotocatalytic C−N Cross‐Coupling
title_short Acridine‐Functionalized Covalent Organic Frameworks (COFs) as Photocatalysts for Metallaphotocatalytic C−N Cross‐Coupling
title_sort acridine‐functionalized covalent organic frameworks (cofs) as photocatalysts for metallaphotocatalytic c−n cross‐coupling
topic Research Articles
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9400916/
https://www.ncbi.nlm.nih.gov/pubmed/35188714
http://dx.doi.org/10.1002/anie.202117738
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