Optically Active Electrochromism of Poly(3,4-ethylenedioxythiophene) Synthesized by Electrochemical Polymerization in Lyotropic Liquid Crystal of Hydroxypropyl Cellulose/Water: Active Control of Optical Activity

Goto, Hiromasa; Akagi, Kazuo

doi:10.1021/cm050755a

Cited by 60 publications

(59 citation statements)

References 42 publications

(45 reference statements)

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“…44 Convincingly instance demonstrated that by covalent attachment of functional groups at the conjugated backbone could obtain novel properties and applications. To achieve chirality of the resulting polymer, different substituted EDOTs bearing chiral glycols, 40,45 chiral octyloxycarbonyl group, 38 L-leucine,…”

Section: Liqi Dong and Baoyang Lu Contributed Equally To This Workmentioning

confidence: 99%

“…38 Enantiomeric molecules exhibit mirror imaged CD spectra of opposite sign. A mono-signate CD of (R)-and (S)-PEDTM-PP films in the doped and dedoped state were illustrated in Figure 5.…”

Section: Spectramentioning

confidence: 99%

“…36,37 (3) The usage of both liquid crystalline conjugated polymer and chiral dopant. 38,39 (4) The copolymerization of dimer or trimer in liquid crystal to obtained copolymer-type chiral polymers. 40,41 Among the aforementioned conducting polymers, one of PTs, poly(3,4-ethylenedioxythiophene) (PEDOT) emerging as a "superstar" material has attracted tremendous attention due to its unique structure and electronic property.…”

Section: Introductionmentioning

confidence: 99%

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

Dong

Duan

et al. 2015

J. Polym. Sci. Part A: Polym. Chem.

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Two new 3,4-ethylenedioxythiophene (EDOT) derivatives, (2R)- (2,3-dihydrothieno[3,4-b][1,4]dioxin-2-yl)methyl 2-phenyl propanoate ((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 (CH 2 Cl 2 ) and terabutylammonium hexafluorophosphate (Bu 4 NPF 6 ) system. As chiral electrodes, poly( (2R)-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.

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Section: Liqi Dong and Baoyang Lu Contributed Equally To This Workmentioning

confidence: 99%

“…38 Enantiomeric molecules exhibit mirror imaged CD spectra of opposite sign. A mono-signate CD of (R)-and (S)-PEDTM-PP films in the doped and dedoped state were illustrated in Figure 5.…”

Section: Spectramentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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

Dong

Duan

et al. 2015

J. Polym. Sci. Part A: Polym. Chem.

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“…HPC in solvent as a polymer CLC system can be conveniently applicable for electrochemical polymerization. HPC was used as a template for production of polymers [8,9].…”

Section: Introductionmentioning

confidence: 99%

Sequential process of chiral imprinting and composite formation allows to produce electrooptically active poly(bis-EDOT)/hydroxypropyl cellulose

Yamabe

Goto

2018

Adv Compos Hybrid Mater

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Poly(3,4-ethylenedioxythiophene) (PEDOT) is one of the promising conjugated polymeric materials for organic devices such as organic solar cell or organic electroluminescence display. Hydroxypropyl cellulose (HPC) is a product of chemical-modified cellulose. HPC shows liquid crystal at appropriate condition in solvents. HPC has been used for a binder of medicines and can be applied for green sustainable chemistry in materials science. In this study, poly(bis-(3,4-ethylenedioxythiophene)), abbreviated as poly(bis-EDOT), film is prepared in cholesteric liquid crystals with electrochemical polymerization. We employ a dimer of EDOT (bis-EDOT) as a monomer because bis-EDOT shows good affinity with liquid crystals and the linear shape of bis-EDOT allows pre-orientation in liquid crystal prior to polymerization. The polymer film thus prepared in cholesteric liquid crystals (CLC) shows characteristic circular dichroism (CD) derived from 3-D asymmetric super structure. This study demonstrates that polymerization of the linear-shaped bis-EDOT can effectively imprint 3-D asymmetric structure from HPC as a polymer CLC matrix and form conductive polymer/non-conductive polymer composite.

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“…Electrochemical polymerization is a useful and convenient method that produces a polymer film on the electrode surface [16,17]. The polymers prepared by asymmetric electrochemical polymerization display intense circular dichroism (CD) in the reduced state, and weaker CD in the oxidized state [18][19][20][21].…”

Section: Introductionmentioning

confidence: 99%

Preparation of iridescent-reflective poly(furan-co-phenylene)s by electrochemical polymerization in a cholesteric liquid crystal medium

Yoneyama

Kawabata

Tsujimoto

et al. 2008

Electrochemistry Communications

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Abstract−Optically active poly(4,4'-di(2-furyl)biphenyl) is successfully prepared by asymmetric electrochemical polymerization in a cholesteric liquid crystal (CLC) electrolyte.The polymer thus obtained forms a fingerprint optical texture similar to that of the CLC electrolyte and a convexo-concave surface structure along the fingerprint pattern. The polymer displays iridescence under irradiation with white light, and circular diffraction upon laser irradiation.

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Optically Active Electrochromism of Poly(3,4-ethylenedioxythiophene) Synthesized by Electrochemical Polymerization in Lyotropic Liquid Crystal of Hydroxypropyl Cellulose/Water: Active Control of Optical Activity

Cited by 60 publications

References 42 publications

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

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

Sequential process of chiral imprinting and composite formation allows to produce electrooptically active poly(bis-EDOT)/hydroxypropyl cellulose

Preparation of iridescent-reflective poly(furan-co-phenylene)s by electrochemical polymerization in a cholesteric liquid crystal medium

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