Linkage Transformations in a Three-Dimensional Covalent Organic Framework for High-Capacity Adsorption of Perfluoroalkyl Substances

Published

November 3, 2023

Author(s)

Andrea Zeppuhar, Devin Rollins, Dale L. Huber, Emmanuel Bazan-Bergamino, Fu Chen, Hayden Evans, Mercedes Taylor

Abstract

Despite their many advantages, covalent organic frameworks (COFs) built from three-dimensional monomers are synthetically difficult to functionalize. Herein, we provide a new synthetic approach to the functionalization of a three-dimensional covalent organic framework (COF-300) by using a series of solid-state linkage transformations. By reducing the imine linkages of the framework to amine linkages, we produced a more hydrolytically stable material and liberated a nucleophilic amino group, poised for further functionalization. We then treated the amine-linked COF with diverse electrophiles to generate a library of functionalized materials, which we tested for their ability to adsorb perfluoroalkyl substances (PFAS) from water. The framework functionalized with dimethylammonium groups, COF-300-dimethyl, adsorbed more than 250 mg of perfluorooctanoic acid (PFOA) per 1 g of COF, which represents an approximately 14,500-fold improvement over that of COF-300 and underscores the importance of electrostatic interactions to PFAS adsorption performance. This work provides a conceptually new approach to the design and synthesis of functional three-dimensional COFs.

Citation

ACS Applied Materials & Interfaces

Volume

15

Issue

45

Pub Type

Journals

Download Paper

https://doi.org/10.1021/acsami.3c12826

Local Download

Keywords

COFs, PFAS

Citation

Zeppuhar, A. , Rollins, D. , Huber, D. , Bazan-Bergamino, E. , Chen, F. , Evans, H. and Taylor, M. (2023), Linkage Transformations in a Three-Dimensional Covalent Organic Framework for High-Capacity Adsorption of Perfluoroalkyl Substances, ACS Applied Materials & Interfaces, [online], https://doi.org/10.1021/acsami.3c12826, https://tsapps.nist.gov/publication/get_pdf.cfm?pub_id=956544 (Accessed October 9, 2025)