General Strategy for Incorporation of Functional Group Handles into Covalent Organic Frameworks via the Ugi Reaction

Alexander Volkov; Jiashan Mi; Kanika Lalit; Puranjan Chatterjee; Dapeng Jing; Scott L Carnahan; Yunhua Chen; Simin Sun; Aaron J Rossini; Wenyu Huang; Levi M Stanley

doi:10.1021/jacs.2c12440

General Strategy for Incorporation of Functional Group Handles into Covalent Organic Frameworks via the Ugi Reaction

J Am Chem Soc. 2023 Mar 22;145(11):6230-6239. doi: 10.1021/jacs.2c12440. Epub 2023 Mar 9.

Authors

Alexander Volkov^{1

2}, Jiashan Mi^{1

2}, Kanika Lalit^{1

2}, Puranjan Chatterjee^{1

2}, Dapeng Jing³, Scott L Carnahan^{1

2}, Yunhua Chen^{1

2}, Simin Sun^{1

2}, Aaron J Rossini^{1

2}, Wenyu Huang^{1

2}, Levi M Stanley¹

Affiliations

¹ Department of Chemistry, Iowa State University, Ames, Iowa 50011, United States.
² U.S. Department of Energy, Ames National Laboratory, Ames, Iowa 50011, United States.
³ Materials Analysis and Research Laboratory, Iowa State University, Ames, Iowa 50011, United States.

PMID: 36892967
DOI: 10.1021/jacs.2c12440

Abstract

The library of imine-linked covalent organic frameworks (COFs) has grown significantly over the last two decades, featuring a variety of morphologies, pore sizes, and applications. An array of synthetic methods has been developed to expand the scope of the COF functionalities; however, most of these methods were designed to introduce functional scaffolds tailored to a specific application. Having a general approach to diversify COFs via late-stage incorporation of functional group handles would greatly facilitate the transformation of these materials into platforms for a variety of useful applications. Herein, we report a general strategy to introduce functional group handles in COFs via the Ugi multicomponent reaction. To demonstrate the versatility of this approach, we have synthesized two COFs with hexagonal and kagome morphologies. We then introduced azide, alkyne, and vinyl functional groups, which could be readily utilized for a variety of post-synthetic modifications. This facile approach enables the functionalization of any COFs containing imine linkages.