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Merging benzotrithiophene covalent organic framework photocatalysis with TEMPO for selective oxidation of organic sulfides

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Abstract

Visible light photocatalysis of covalent organic frameworks (COFs) has made significant progress in recent years. Benzotrithiophene (BTT), a planar, electron-rich building block, turns out to be foundational in assembling COFs in which the full π-conjugation of BTT is essential to facilitate electron transfer. Herein, a sp2 carbon-conjugated COF, namely BTT-sp2c-COF, is assembled from benzo[1,2-b:3,4-b′:5,6-b″]trithiophene-2,5,8-tricarbaldehyde and [1,1′:4′,1″-terphenyl]-4,4″-dicarbonitrile towards photocatalysis. More importantly, TEMPO (2,2,6,6-tetramethylpiperidin-1-yl)oxyl, 1 mol%) could considerably accelerate the selective oxidation of organic sulfides with O2 over BTT-sp2c-COF. TEMPO mediates hole transfer between BTT-sp2c-COF and organic sulfides, and O-atoms are incorporated into sulfoxides via an electron transfer pathway. Merging BTT-sp2c-COF photocatalysis with TEMPO generally applies to transforming organic sulfides into sulfoxides. This work implies the full π-conjugation of electron-rich building blocks into COFs is a viable strategy for selective visible light photocatalysis.

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Acknowledgements

This work was supported by the National Natural Science Foundation of China (22072108). The numerical calculations were done on the supercomputing system in the Supercomputing Center of Wuhan University. We also acknowledge the Core Facility of Wuhan University and the Center for Electron Microscopy at Wuhan University for support to materials characterizations.

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Authors and Affiliations

  1. Sauvage Center for Molecular Sciences, Hubei Key Lab on Organic and Polymeric Optoelectronic Materials, College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, 430072, China

    Fengwei Huang, Yuexin Wang, Xiaoyun Dong & Xianjun Lang

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  1. Fengwei Huang
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  2. Yuexin Wang
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  3. Xiaoyun Dong
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  4. Xianjun Lang
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Correspondence to Xianjun Lang.

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The supporting information is available online at chem.scichina.com and link.springer.com/journal/11426. The supporting materials are published as submitted, without typesetting or editing. The responsibility for scientific accuracy and content remains entirely with the authors.

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11426_2023_1644_MOESM1_ESM.docx

Merging benzotrithiophene covalent organic framework photocatalysis with TEMPO for selective oxidation of organic sulfides

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Huang, F., Wang, Y., Dong, X. et al. Merging benzotrithiophene covalent organic framework photocatalysis with TEMPO for selective oxidation of organic sulfides. Sci. China Chem. 66, 3290–3296 (2023). https://doi.org/10.1007/s11426-023-1644-x

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  • DOI: https://doi.org/10.1007/s11426-023-1644-x

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