Matúš Chvojka, Hennie Valkenier and Vladimír Šindelář
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Synthesis of bambusurils with perfluoroalkylthiobenzyl groups as highly potent halide receptors†
The preparation of anion receptors with ultrahigh binding affinities is an important, yet challenging, topic of supramolecular chemistry. The search for new structural motifs which would enhance the performance of anion receptors is therefore an important task. In this context, we report the synthesis of novel fluorinated bambus[6]urils that incorporate unique benzyl substituents with perfluoroalkylthio groups, aimed at enhancing their anion receptor capabilities. The synthetic strategy developed allows for the efficient preparation of these structural motifs. Ultrahigh stability of the complexes between halides and the prepared bambus[6]urils was observed and quantified using 19F NMR competition experiments. Replacing –CF3 groups on benzylated bambus[6]urils by –SCF3 groups increased the affinity of the macrocycles towards anions and provided the strongest iodide receptor reported with a binding affinity of 4 × 1013 M−1 in acetonitrile.
期刊介绍:
Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.