Siderophore-inspired chelator hijacks uranium from aqueous medium.

Over millennia, nature has evolved an ability to selectively recognize and sequester specific metal ions by employing a wide variety of supramolecular chelators. Iron-specific molecular carriers-siderophores-are noteworthy for their structural elegance, while exhibiting some of the strongest and most selective binding towards a specific metal ion. Development of simple uranyl (UO) recognition motifs possessing siderophore-like selectivity, however, presents a challenge. Herein we report a comprehensive theoretical, crystallographic and spectroscopic studies on the UO binding with a non-toxic siderophore-inspired chelator, 2,6-bis[hydroxy(methyl)amino]-4-morpholino-1,3,5-triazine (HBHT). The optimal pK values and structural preorganization endow HBHT with one of the highest uranyl binding affinity and selectivity among molecular chelators. The results of small-molecule standards are validated by a proof-of-principle development of the HBHT-functionalized polymeric adsorbent material that affords high uranium uptake capacity even in the presence of competing vanadium (V) ions in aqueous medium.