Enantioselective Recognition and Separation of C2 Symmetric Substances via Chiral Metal-Organic Frameworks.

Abstract

A promising route toward the enantioselective recognition and separation of racemic molecules is the design of chiral metal-organic frameworks (CMOFs) with high enantioselectivity and stability. Herein, we report porous CMOFs Δ- and Λ-RuEu-MOFs constructed from the D3-symmetry helical chiral Ru(phen)3-derived tricarboxylate ligand and Eu2 units, which can be utilized as adsorbents for the enantioselective recognition and separation of 1,1'-bi-2-naphthol (BINOL) derivatives. Investigation of the circular dichroism enantiodifferentiation between the host and guest suggested that Δ- and Λ-RuEu-MOFs can be employed as chiral sensors to discriminate axial enantiomers due to their diastereomeric host-guest relationship. Density functional theory calculations reveal that chiral recognition is attributed to the distinguishing binding affinities stemming from N···H-O hydrogen bonds and π-π stacking between the host and guest. Moreover, the reticulate structure of Δ- and Λ-RuEu-MOFs can be readily recycled and reused for the successive enantioselective separation of BINOL up to 80% ee.