Carbamate triserine lactone receptors for anion recognition

Abstract

We have taken advantage of the ability of the cyclic triester of l-serine to organize ligand units appended to the three α-amine functionalities, as in enterobactin, a siderophore produced by enteric bacteria that binds ferric ion exceptionally well ( K f = 10 49). As an extension of the preorganization concept, this work describes the preparation and characterization of carbamate triserine lactone receptors 1– 6 and their ability to act as molecular receptors for anions. These receptors bind halides (F − ≫ Cl − > Br − > I −) with binding constants K in the range 21–7350 L mol −1.