Citation: 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. Synthesis and Characterization of D-/L-methionine Grafted PEDOTs for Selective Recognition of 3,4-Dihydroxyphenylalanine Enantiomers[J]. Chinese Journal of Polymer Science, ;2016, 34(5): 563-577. doi: 10.1007/s10118-016-1772-x shu

Synthesis and Characterization of D-/L-methionine Grafted PEDOTs for Selective Recognition of 3,4-Dihydroxyphenylalanine Enantiomers

School of Pharmacy, Jiangxi Science & Technology Normal University, Nanchang 330013, China

Corresponding author: Xue-min Duan, duanxuemin@126.com Jing-kun Xu, xujingkun@tsinghua.org.cn

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Received Date: 31 October 2015
Revised Date: 5 December 2015
Accepted Date: 5 December 2015

Fund Project: Provincial Project for Postgraduate Innoviation in Jiangxi Science and Technology Normal University YC2014-X27This work was financially supported by the National Natural Science Foundation of China 51263010the Science and Technology Landing Plan of Universities in Jiangxi Province KJLD14069This work was financially supported by the National Natural Science Foundation of China 51272096This work was financially supported by the National Natural Science Foundation of China 51303073Natural Science Foundation of Jiangxi Province 20142BAB206028

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.
- Chiral,
- Poly(3,4-ethylenedioxythiophene) derivatives,
- Synthesis,
- Chiral recognition,
- 3,4-Dihydroxy-phenylalanine
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