Synthesis of crown ether-based microporous organic networks: A new type of efficient adsorbents for chlorophenols

J Hazard Mater. 2023 Feb 5;443(Pt B):130268. doi: 10.1016/j.jhazmat.2022.130268. Epub 2022 Oct 27.

Abstract

Microporous organic networks (MONs) are a booming class of functional materials in elimination of environmental pollutants. However, the limit varieties of MONs still restrict their broad applications. Here we report the synthesis of a novel type of crown ether (CE)-based MONs via the coupling between brominated 18-crown-6 ether and different aromatic alkynyls. The constructed CE-based MONs integrates the good conjugation property of MONs and the inherent host-guest binding sites of CE, allowing the ultrafast and efficient adsorption and removal of a typical environmental priority pollutant 2,4,6-trichlorophenol (2,4,6-TCP). The hydrophobic CE-based MONs can also address the recovery challenge of unstable discrete CE in most organic and inorganic solvents. All CE-based MONs displayed fast adsorption kinetics (< 3 min) and large adsorption capacities (229.1-341.7 mg g-1) for 2,4,6-TCP. The CE-based MONs also gave stable adsorption capacities for 2,4,6-TCP in pH range of 4.0-6.0, NaCl concentration of 0-40 mg L-1, HA concentration of 0-30 mg L-1, or H2O2 ratio of < 5 %. Density functional theory calculation, Fourier transform infrared and X-ray photoelectron spectra evaluation revealed adsorption process involved hydrophobic, π-π and hydrogen bonding interactions. The CE-based MONs also showed favorable reusability and good adsorption for other toxic chlorophenols. This work highlights the potential of CE-based MONs in contaminants elimination.

Keywords: Chlorophenols; Crown ether; Host-guest interaction; Microporous organic networks; Water treatment.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adsorption
  • Chlorophenols* / chemistry
  • Crown Ethers*
  • Environmental Pollutants* / chemistry
  • Hydrogen Peroxide
  • Water Pollutants, Chemical* / analysis

Substances

  • Chlorophenols
  • Crown Ethers
  • Hydrogen Peroxide
  • Environmental Pollutants
  • Water Pollutants, Chemical