Enantiomers being mirror images to each other are difficult to distinguish using simple chemical reaction. The quest for guest molecules capable of discriminating enantiomers are not new but until recently chiral recognition mechanism was largely based on molecular simulations as structurally characterized host-guest complexes are hard to come by. Our quest to synthesize chiral host molecule, started with designing flexible multi-dentate ligands based on natural amino acid and first row transition metal ions. Over the years, we have synthesized number of different architectures (Figure ) and tested their capability to accommodate guest enantiomer. Learning from those failures and incorporating necessary changes eventually led us to a binuclear Ni(II) complex anion which is capable of distinguishing enantiomers of several amino alcohols in their cationic form. Most of these amino alcohols occur in nature and plays important role as neurotransmitter. They were chosen because of their structural similarity to adrenaline which is a hormone, neurotransmitter, as well as medication. Chiral enhancement varies from 68% to ~100% depending on the amino alcohol used. Structural characterization of the host-guest salts along with HPLC on the bulk revealed the recognition mechanism in details.

Chiral recognition of amino alcohols using binuclear Ni(II) complex anion as host

255th National Meeting (2018)

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