Molecular and nano structures of chiral PEDOT derivatives influence the enantiorecognition of biomolecules. analysis of chiral recognition.

In this study we investigated the synergistic effects of the chirality (molecular structure) and surface morphology (nanostructure) of a newly designed sensing platform for the stereoselective recognition of biomolecules. We synthesized 3,4-ethylenedioxythiophene monomers presenting an OH functional group on the side chain (EDOT-OH) with either or chirality and then electropolymerized them in a template-free manner to engineer poly(EDOT-OH) nanotubes and smooth films with or chirality. We used a quartz crystal microbalance (QCM) to examine the differential binding of fetal bovine serum, RGD peptide, insulin, and ()- and ()-mandelic acid (MA) on these chiral polymeric platforms. All of these biomolecules bound stereoselectively and with greater affinity toward the nanotubes than to the smooth films. The sensitive chiral recognition of ()- and ()-MA on the ()-poly(EDOT-OH) nanotube surface occurred with the highest chiral discrepancy ratio of 1.80. experiments revealed a greater degree of protein deposition from MCF-7 cells on the chiral nanotube surfaces. We employed molecular dynamics simulations and density functional theory calculations to investigate the mechanism underlying the sensitive chiral recognition between the chiral sensing platforms and the chiral analyte molecules.