Rational Design of π‐Conjugated Polymers for Enantioselective Recognition of Amino Acids

ABSTRACT Chiral conducting polymers have gained considerable attention as specific environments for enantioselective recognition, separation and synthesis. In this work, we report the rational design of a specific class of conducting polymers with chiral features for the enantiodiscrimination of amino acids. This is achieved by introducing chiral features on the trimer unit bis[3,4‐ethylenedioxythiophene]‐thiophene via the functionalization of the β‐position of the thiophene with the enantiomers of two different amino acids, serine and cysteine. The electrochemical polymerization produces films showing reversible charging/discharging ( Q c / Q a ≈ 1), with electric properties characterized by a charge hopping mechanism. The electrochemical and electrical features of the corresponding enantiomers of the polymers nearly overlap, demonstrating that the charging/discharging processes of these materials are identical regardless of their chiral nature. Finally, the enantioselectivity of the films with respect to amino acids is revealed by significant differences of the current and charge. This type of soft materials allows envisioning their possible use for the design of flexible enantioselective organic transistors for biological applications.