Synthesis and characterization of D-/L-methionine grafted PEDOTs for selective recognition of 3,4-dihydroxyphenylalanine enantiomers

Li qi Dong, Du fen Hu, Xue min Duan*, Zhi peng Wang, Kai xin Zhang, Xiao fei Zhu, Hui Sun, You shan Zhang, Jing kun Xu

*Corresponding author for this work

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

Two pairs of amino-acid functionalized poly(3,4-ethylenedioxythiophene) (PEDOT) derivatives, namely, poly(N-(tert-butoxycarbonyl)-L-methionyl (3,4-ethylenedioxythiophene-2’-yl)methylamide) (L-PEDOT-Boc-Met) and poly(N-(tert-butoxycarbonyl)-D-methionyl (3,4-ethylenedioxythiophene-2’-yl)methylamide) (D-PEDOT-Boc-Met); poly(L-methionyl (3,4-ethylenedioxythiophene-2’-yl)methylamide) (L-PEDOT-Met) and poly(D-methionyl (3,4-ethylenedioxythiophene-2’-yl)methylamide) (D-PEDOT-Met) were synthesized via chemical oxidative polymerization of corresponding monomers. The structural characterization, spectroscopic properties and thermal stability of these monomers and polymers were systematically explored by FTIR spectra, Raman spectra, XRD spectra, UV-Vis spectra and thermogravimetric analysis. As chiral electrode materials, these polymers were employed to successfully recognize 3,4-dihydroxyphenylalanine (DOPA) enantiomers by cyclic voltammetry (CV) in sulphuric acid solution. The measurement results reveal that the tendency was hetero-chiral interaction between L-PEDOT-Met/PVA/GCE and D-DOPA, D-PEDOT-Met/PVA/GCE and L-DOPA, respectively. Also, the mechanism of chiral discrimination was discussed. All the results implied that the combination of electrochemical molecular recognition technology and chiral PEDOT materials can be a promising approach for chiral recognition and may open new opportunities for facile, biocompatible, sensitive and robust chiral assays in biochemical applications.

Original languageEnglish
Pages (from-to)563-577
Number of pages15
JournalChinese Journal of Polymer Science (English Edition)
Volume34
Issue number5
DOIs
Publication statusPublished - 1 Apr 2016
Externally publishedYes

Keywords

  • 3,4-Dihydroxy-phenylalanine
  • chiral
  • chiral recognition
  • poly(3,4-ethylenedioxythiophene) derivatives
  • synthesis

Fingerprint Dive into the research topics of 'Synthesis and characterization of D-/L-methionine grafted PEDOTs for selective recognition of 3,4-dihydroxyphenylalanine enantiomers'. Together they form a unique fingerprint.

  • Cite this