Tailor-Made Supramolecular Chirogenic System Based on C s ‑Symmetric Rigid Organophosphoric Acid Host and Amino Alcohols: Mechanistic Studies, Bulkiness Effect, and Chirality Sensing

A C s -symmetric, rigid, achiral organophosphoric acid host with differentiable tautomeric structures has been developed for induced circular dichroism (ICD) studies of vicinal amino alcohols. The structural features of the host and the substituent bulkiness of the guest, together, decide the preferred mode of hydrogen binding on equilibration with a resultant ICD signal. An unequivocal rule correlating the absolute configuration of the guest amino alcohol with the ICD outcome is proposed.