Phenyl-Extended Resorcin[4]arenes: Synthesis and Highly Efficient Iodine Adsorption

Angew Chem Int Ed Engl. 2024 Oct 21;63(43):e202411261. doi: 10.1002/anie.202411261. Epub 2024 Aug 12.

Abstract

The continuous exploration of new analogs of calixarenes and pillararenes unlocks infinite opportunities in supramolecular chemistry and materials. In this work, we introduce a new class of macrocycle, phenyl-extended resorcin[4]arenes (ExR4), a unique and innovative design that incorporates unsubstituted phenylene moieties into the resorcin[4]arene scaffold. Single-crystal analysis reveals a chair-like conformation for per-methylated ExR4 (Me-ExR4) and a twisted "Figure-of-eight" shaped conformation for per-hydroxylated ExR4 (OH-ExR4). Notably, OH-ExR4 demonstrates exceptional adsorption capability toward I3 - ions in an aqueous solution, with a rapid kinetic rate of 1.18×10-2 g ⋅ mg-1 ⋅ min-1. Furthermore, OH-ExR4 shows excellent recyclability and potential as a stationary phase in column setups. The discovery of ExR4 opens up new avenues for constructing new macrocycles and inspires further research in functional adsorption materials for water pollutant removal.

Keywords: Iodine adsorption; Macrocyclic arenes; Resorcin[4]arene; Supramolecular chemistry; Synthetic macrocycle.