Preparation of Versatile, Porous Poly-Arylthioethers by Reversible Pd-Catalysed C–S/C–S Metathesis

23 February 2021, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

Porous organic frameworks have shown a number of promising properties; however, their industrial application is usually hampered due to the lability of their linkages (imine, boroxine, etc.). Inspired by the outstanding chemical, mechanical and thermal resistance of the 1D polymer polyphenylene sulfide (PPS), we hypothesized that 2D and 3D poly-arylthioether frameworks would merge the attractive features common to porous frameworks and PPS in a single material. Herein, we report a Pd-catalysed C–S/C–S metathesis-based method to prepare new porous poly-arylthioether frameworks in good yields. The self-correcting nature of the process has enabled the synthesis of new, robust materials with high surface areas. Despite the frameworks’ extreme resistance to harsh chemicals, they can be fully recycled to recover the original building blocks using the same catalytic reaction. In addition, we demonstrate preliminary results showing that these materials have great potential in several environmentally relevant applications including metal capture, metal sensing and heterogeneous catalysis. In a broader context, these results clearly demonstrate the untapped potential of emerging single-bond metathesis reactions in the preparation of new materials.

Keywords

Porous Frameworks
homogeneous catalysis
metathesis chemistry
Polymer chemistry
metal capture
metal sensing
heterogeneous catalysis

Supplementary materials

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