Development of Porous Organic Polymers as Metal‐Free Photocatalysts for the Aromatization of N‐Heterocycles

Author:

Debruyne Maarten1ORCID,Raeymackers Nathan1ORCID,Vrielinck Henk2ORCID,Radhakrishnan Sambhu3ORCID,Breynaert Eric3ORCID,Delaey Maxime2ORCID,Laemont Andreas4ORCID,Leus Karen5ORCID,Everaert Jonas1ORCID,Rijckaert Hannes4ORCID,Poelman Dirk2ORCID,Morent Rino5ORCID,De Geyter Nathalie5ORCID,Van Der Voort Pascal4ORCID,Van Speybroeck Veronique6ORCID,Stevens Christian V.1ORCID,Heugebaert Thomas S. A.1ORCID

Affiliation:

1. Department of Green Chemistry and Technology Ghent University Coupure Links 653 9000 Ghent Belgium

2. Department of Solid State Sciences Ghent University Krijgslaan 281 (S1) 9000 Ghent Belgium

3. NMRCoRe – NMR/X-Ray platform for Convergence Research KU Leuven Celestijnenlaan 200 f – box 2461 3001 Leuven Belgium

4. Department of Chemistry Ghent University Krijgslaan 281 (S3) 9000 Ghent Belgium

5. Research Unit Plasma Technology Department of Applied Physics Ghent University Sint-Pietersnieuwstraat 41 (B4) 9000 Ghent Belgium

6. Department of Applied Physics Ghent University Technologiepark 46 9052 Zwijnaarde Belgium

Abstract

AbstractPorous 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.

Funder

Vlaamse regering

Publisher

Wiley

Subject

Inorganic Chemistry,Organic Chemistry,Physical and Theoretical Chemistry,Catalysis

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