Novel chiral PEDOTs for selective recognition of 3,4-dihydroxyphenylalanine enantiomers: synthesis and characterization

Liqi Dong, Baoyang Lu, Xuemin Duan*, Jingkun Xu, Dufen Hu, Kaixin Zhang, Xiaofei Zhu, Hui Sun, Shouli Ming, Zhipeng Wang, Shijie Zhen

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

13 Citations (Scopus)

Abstract

Two new 3,4-ethylenedioxythiophene (EDOT) derivatives, (2R)-(2,3-dihydrothieno[3,4-b][1,4]dioxin-2-yl)methyl 2-phenylpropanoate ((R)-EDTM-PP) and (2S)-(2,3-dihydrothieno[3,4-b][1,4]dioxin-2-yl)methyl 2-phenylpropanoate ((S)-EDTM-PP), were synthesized and electropolymerized in dichloromethane (CH2Cl2) and terabutylammonium hexafluorophosphate (Bu4NPF6) system. As chiral electrodes, poly((2R)-(2,3-dihydrothieno[3,4-b][1,4]dioxin-2-yl)methyl 2-phenylpropanoate) ((R)-PEDTM-PP) and poly((2S)-(2,3-dihydrothieno[3,4-b][1,4]dioxin-2-yl)methyl 2-phenylpropanoate) ((S)-PEDTM-PP)-modified glassy carbon electrodes (GCEs) were employed to successfully recognize 3,4-dihydroxyphenylalanine (DOPA) enantiomers. Cyclic voltammetry presents that (R)-PEDTM-PP and (S)-PEDTM-PP had good redox activity and stability. Spectroelectrochemistry studies revealed (R)-PEDTM-PP and (S)-PEDTM-PP polymers have electronic bandgap of 1.68 and 1.66 eV, and could be reversibly oxidized and reduced accompanying with obvious color changes from dark blue to light purple. In addition, the electrochemical behavior, structural characterization, thermal stability, morphology and circular dichroism of (R)-PEDTM-PP and (S)-PEDTM-PP films were investigated in detail.

Original languageEnglish
Pages (from-to)2238-2251
Number of pages14
JournalJournal of Polymer Science, Part A: Polymer Chemistry
Volume53
Issue number19
DOIs
Publication statusPublished - 1 Oct 2015
Externally publishedYes

Keywords

  • characterization
  • chiral
  • chiral discrimination
  • conducting polymer
  • synthesis

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