Calix[4]pyrrole-Crosslinked Porous Polymeric Networks for the Removal of Micropollutants from Water

Xiaohua Wang; Linhuang Xie; Kunhua Lin; Weibin Ma; Tian Zhao; Xiaofan Ji; Mram Alyami; Niveen M Khashab; Hongyu Wang; Jonathan L Sessler

doi:10.1002/anie.202016364

Calix[4]pyrrole-Crosslinked Porous Polymeric Networks for the Removal of Micropollutants from Water

Angew Chem Int Ed Engl. 2021 Mar 22;60(13):7188-7196. doi: 10.1002/anie.202016364. Epub 2021 Feb 17.

Authors

Xiaohua Wang¹, Linhuang Xie¹, Kunhua Lin¹, Weibin Ma¹, Tian Zhao², Xiaofan Ji³, Mram Alyami⁴, Niveen M Khashab⁴, Hongyu Wang¹, Jonathan L Sessler^{1

2}

Affiliations

¹ Department of Chemistry, College of Science, and Center for Supramolecular Chemistry & Catalysis, Shanghai University, 99 Shangda Road, Shanghai, 200444, China.
² Department of Chemistry, The University of Texas at Austin, 105 E. 24th Street A5300, Austin, TX, 78712, USA.
³ Key Laboratory of Material Chemistry for Energy Conversion and Storage, Ministry of Education, Hubei Key Laboratory of Material Chemistry and Service Failure, School of Chemistry and Chemical Engineering, Huazhong University of Science and Technology, Wuhan, 430074, China.
⁴ Smart Hybrid Materials Laboratory, Physical Science and Engineering Division, King Abdullah University of Science and Technology, Thuwal, 23955-6900, Kingdom of Saudi Arabia.

PMID: 33354826
DOI: 10.1002/anie.202016364

Abstract

Calix[4]pyrrole-based porous organic polymers (P1-P3) for removing organic micropollutants from water were prepared. A bowl-shaped α,α,α,α-tetraalkynyl calix[4]pyrrole and diketopyrrolopyrrole monomer were crosslinked via Sonogashira coupling to produce a 3D network polymer, P1. P1 proved too hydrophobic for use as an adsorbent and was converted to the corresponding neutral polymer P2 (containing carboxylic acid groups) and its anionic derivative P3 (containing carboxylate anion groups). Anionic P3 outperformed P2 in screening studies involving a variety of model organic micropollutants of different charge, hydrophilicity and functionality. P3 proved particularly effective for cationic micropollutants. The theoretical maximum adsorption capacity (q_max,e ) of P3 reached 454 mg g^-1 for the dye methylene blue, 344 mg g^-1 for the pesticide paraquat, and 495 mg g^-1 for diquat. These uptake values are significantly higher than those of most synthetic adsorbent materials reported to date.

Keywords: adsorption; calix[4]pyrrole; diketopyrrolopyrrole; micropollutants; porous organic polymers.

Publication types

Research Support, Non-U.S. Gov't