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Surface Functionalization of Metal-Organic Frameworks for Improved Moisture Resistance
Published on: September 5, 2018
Embedding Hydrogen Atom Transfer Moieties in Covalent Organic Frameworks for Efficient Photocatalytic C-H
Huaji Pang1,2, Gang Liu1, Dekang Huang1
1College of Chemistry, Huazhong Agricultural University, 430070, Wuhan, P. R. China.
Novel covalent organic frameworks (COFs) with embedded active sites enable efficient photocatalytic C-H functionalization. These new materials show high yields and stability for complex organic transformations.
Area of Science:
- Materials Science
- Organic Chemistry
- Photocatalysis
Background:
- Covalent organic frameworks (COFs) are effective heterogeneous photocatalysts for simple reactions.
- Their use in complex transformations like C-H bond functionalization is limited by a lack of active catalytic cores.
Purpose of the Study:
- To develop novel COFs with embedded hydrogen atom transfer (HAT) moieties for enhanced photocatalytic activity.
- To investigate the application of these COFs in site-selective functionalization of unactivated C-H bonds.
Main Methods:
- Synthesized nonsubstituted quinoline-linked COFs (NQ-COFs) with oxygen atoms bonded at the N-terminus.
- Designed a novel COF (NQ-COFE5 -O) integrating photosensitizer and HAT catalyst functionalities.
- Evaluated the photocatalytic performance on ten diverse substrates.
Main Results:
- NQ-COFE5 -O demonstrated significantly higher efficiency in C-H functionalization compared to NQ-COFE5.
- Achieved moderate to high yields (up to 93%) for various substrates including quinolines, benzothiazole, and benzoxazole.
- The NQ-COFE5 -O catalyst exhibited excellent photostability and recyclability over five cycles.
Conclusions:
- Embedding active HAT moieties into COF skeletons is a viable strategy for creating advanced photocatalysts.
- The developed NQ-COFE5 -O is a highly efficient and stable catalyst for complex C-H functionalization reactions.
- This work expands the application scope of COFs in challenging organic synthesis.
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