Sustainable Porous Polymer Catalyst for Size-Selective Cross-Coupling Reactions

Abstract

A new, high surface area, nanoporous polymer (COP-220) was synthesized using sustainable building blocks, namely, a food coloring dye (erythrosine B) and a commercial alkyne. During the Sonogashira coupling, it is observed that Pd and Cu ions and triphenylphosphine ligands of the catalyst get trapped inside the pores. The remnant synthesis catalyst components were characterized in detail and were tested as a new catalyst for Suzuki–Miyaura coupling reactions. COP-220 showed conversion yields comparable to the commercial homogeneous catalyst Pd­(PPh3)2Cl2 with an additional advantage of size-dependent catalytic activity when bulkier substrates were used. COP-220 was highly stable under thermal and chemical treatments and recyclable with no loss of activity. These findings show a clear need for extensive characterization of nanoporous polymers made through cross-coupling reactions and the potential of the trapped catalysts for new catalytic activity without additional loading.

The mechanochemical Friedel‐Crafts polymerization as a solvent‐free cross‐linking approach toward microporous polymers

“…The interest in porous materials steadily increased within the last decades, which is attributed to their versatile applicability in several fields of industrial relevance, such as in gas and energy storage, in molecular separation or in catalysis 1–13 . While porous materials can be classified regarding their pore sizes as macroporous (pore sizes of >50 nm), as mesoporous (pore sizes of 2–50 nm) or as microporous (pore sizes of <2 nm), the term furthermore includes a variety of different material classes, such as zeolites, carbons or porous metal oxides 14–25 .…”

Upgraded Heterogenization of Homogeneous Catalytic Systems by Hollow Porous Organic Frameworks with Hierarchical Porous Shell for Efficient Carbon Dioxide Conversion

“…Powder Xray diffraction (PXRD) patterns indicated that the HPOFs are amorphous due to the irreversibility of Sonogashira crosscoupling reaction (Figure S4). [20] Thermogravimetric analysis (TGA) indicates the HPOFs materials are stable before 220 °C (Figure S5).…”

“…It should be mentioned that the FTIR and solid‐state 13 C NMR spectra of HPOFs are almost identical with each other, indicating morphology and shell thickness has no obvious effect on the compositions and structures of HPOFs. Powder X‐ray diffraction (PXRD) patterns indicated that the HPOFs are amorphous due to the irreversibility of Sonogashira cross‐coupling reaction (Figure S4) [20] . Thermogravimetric analysis (TGA) indicates the HPOFs materials are stable before 220 °C (Figure S5).…”

Triazatruxene-Based Ordered Porous Polymer: High Capacity CO2, CH4, and H2 Capture, Heterogeneous Suzuki–Miyaura Catalytic Coupling, and Thermoelectric Properties

“…It was observed from the thermogravimetric analysis (TGA) spectrum (Figure S6) that TATHCP-Pd is stable up to 450 °C, meeting potential application requirements in catalysis that usually occur at elevated temperatures. The interest in the use of recycled palladium catalysts in industrial applications remains attractive due to the difficulties encountered in the recycling and separation of expensive palladium catalysts. − …”