TY - JOUR
T1 - Novel chiral PEDOTs for selective recognition of 3,4-dihydroxyphenylalanine enantiomers
T2 - synthesis and characterization
AU - Dong, Liqi
AU - Lu, Baoyang
AU - Duan, Xuemin
AU - Xu, Jingkun
AU - Hu, Dufen
AU - Zhang, Kaixin
AU - Zhu, Xiaofei
AU - Sun, Hui
AU - Ming, Shouli
AU - Wang, Zhipeng
AU - Zhen, Shijie
PY - 2015/10/1
Y1 - 2015/10/1
N2 - 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.
AB - 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.
KW - characterization
KW - chiral
KW - chiral discrimination
KW - conducting polymer
KW - synthesis
UR - http://www.scopus.com/inward/record.url?scp=84942294562&partnerID=8YFLogxK
U2 - 10.1002/pola.27695
DO - 10.1002/pola.27695
M3 - Article
AN - SCOPUS:84942294562
SN - 0887-624X
VL - 53
SP - 2238
EP - 2251
JO - Journal of Polymer Science, Part A: Polymer Chemistry
JF - Journal of Polymer Science, Part A: Polymer Chemistry
IS - 19
ER -