Synthesis and characterization of chiral PEDOT enantiomers bearing chiral moieties in side chains: chiral recognition and its mechanism using electrochemical sensing technology?

RSC Advances Pub Date: 2016-01-18 DOI: 10.1039/C5RA20871H

Abstract

In this work, we present a pair of chiral PEDOT derivatives named poly((R)-2-(chloromethyl)-2,3-dihydrothieno[3,4-b][1,4]dioxine) ((R)-PEDTC) and poly((S)-2-(chloromethyl)-2,3-dihydrothieno[3,4-b][1,4]dioxine) ((S)-PEDTC), which were employed as excellent chiral recognition materials for fabricating chiral sensors and then discriminating between 3,4-dihydroxyphenylalanine (DOPA) enantiomers. Importantly, the mechanism of the stereospecificity of the interaction between the DOPA enantiomers and chiral polymers was discussed specifically. A series of performances of corresponding polymers were characterized in some detail using different strategies including CV, CD, FT-IR, UV-vis, SEM, and TG. The CD spectrum indicated that (R)-PEDTC and (S)-PEDTC are mirror symmetric. CV shows that the polymers had superior redox reversibility in CH3CN–Bu4NPF6. Finally, different electrochemical methods including CV, square wave voltammetry (SWV) and differential pulse voltammetry (DPV) were introduced for the discrimination of DOPA enantiomers. Satisfactory measurement results demonstrated that (R)-PEDTC/GCE and (S)-PEDTC/GCE exhibited excellent enantioselectivity of DOPA enantiomers and the tendency was for anisotropic interaction between (R)-PEDTC and L-DOPA, and (S)-PEDTC and D-DOPA. This implied that the obtained polymer films could be promising candidates as enantioselective materials in the electrochemical sensor field.

Graphical abstract: Synthesis and characterization of chiral PEDOT enantiomers bearing chiral moieties in side chains: chiral recognition and its mechanism using electrochemical sensing technology
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