Tetradentate halogen bonding macrocyclic anion receptor inspired by the “Texas-sized” molecular box?

Organic & Biomolecular Chemistry Pub Date: 2022-01-13 DOI: 10.1039/D1OB02381K

Abstract

Inspired by the tetracationic “Texas-sized” molecular box, a neutral analogue containing four iodotriazole halogen bond-promoting subunits (“Ibox”) was synthesized. This new macrocycle was prepared by means of azide–alkyne click chemistry. It was found to recognize Cl?, Br? and I? anions (as their tetrabutylammonium salts) in CDCl3. 1H NMR spectroscopic titrations revealed a higher affinity for the heavier halide anions and provided support for a preferred 1?:?2 binding stoichiometry.

Graphical abstract: Tetradentate halogen bonding macrocyclic anion receptor inspired by the “Texas-sized” molecular box
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