Electroactive polymer sensors for chiral amines based on optically active 1,1′-binaphthyls

Molecular chirality is vital in biological functions and discriminating such chirality is important in organic synthesis, bio-synthesis, medicinal chemistry, and drug development. We developed electroactive chiral sensors by incorporating binaphthol moieties into the polymer main chains. The binaphthyl scaffold of the binaphthol moiety recognizes one form of chirality from the other, and its phenol groups play a vital role in the charge transporting mechanism. Aiming for chiral amine sensors, we synthesized binaphthol-containing electropolymerizable monomers and polymerized to produce proton-dopable chiral polymers, which were characterized by cyclic voltammetry, potentiometry, and in situ conductivity measurements. Chiral discriminating ability of the resulting polymers was tested and their sensing mechanism was proposed.