A host molecule, capable of freely adopting P or M helicity, is described for molecular recognition and chirality sensing. The host, consisting of a biphenol core, binds chiral amines via hydrogen-bonding interactions. The diastereomeric complex will favor either P or M helicity as a result of minimizing steric interactions of the guest molecule with the binding cavity of the host, resulting in a detectable exciton-coupled circular dichroic spectrum. A working model is proposed that enables non-empirical prediction of the chirality of the bound amine.

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