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Construction of Ultrastable Nonsubstituted Quinoline‐Bridged Covalent Organic Frameworks via Rhodium‐Catalyzed Dehydrogenative Annulation

Xiaodong Zhao, Huaji Pang, Dekang Huang, Gang Liu, Jianxiang Hu, Yonggang Xiang

2022Angewandte Chemie International Edition74 citationsDOI

Abstract

Exploring new routes to lock the dynamic C=N bonds in imine-linked covalent organic frameworks (COFs) is highly desired for enhancing their stability and functionality. Herein, a novel C=N bridge locking strategy via rhodium-catalyzed [4+2] annulation is developed to construct nonsubstituted quinoline-linked COFs (NQ-COFs). The notable feature of this strategy includes high C=N conversion efficiency, oxidant-free, and generality for synthesis of a variety of NQ-COFs with high chemical stability. Particularly, after post-synthetic modification, the crystallinity, topology, and porosity of pristine imine-linked COFs are well retained. When used as photocatalysts, NQ-COFs display better visible light absorption and carriers' separation efficiency due to enhanced in-plane π conjugation ability, as well as more facile generation of superoxide anion radicals than their counterparts, thus leading to efficient synthesis of 2,4,6-tris(aryl)pyridines, benzimidazole, and sulfoxide derivatives.

Topics & Concepts

ImineAnnulationChemistryCovalent bondRhodiumRadicalCombinatorial chemistryBenzimidazoleQuinolineCatalysisOrganic chemistryCovalent Organic Framework ApplicationsAdvanced Photocatalysis TechniquesMetal-Organic Frameworks: Synthesis and Applications
Construction of Ultrastable Nonsubstituted Quinoline‐Bridged Covalent Organic Frameworks via Rhodium‐Catalyzed Dehydrogenative Annulation | Litcius