Dataset Information

Facile Synthesis of a 3,4-Ethylene-Dioxythiophene (EDOT) Derivative for Ease of Bio-Functionalization of the Conducting Polymer PEDOT.

ABSTRACT: In the pursuit of conducting polymer based bio-functional devices, a cost-effective and high yield synthesis method for a versatile monomer is desired. We report here a new synthesis strategy for a versatile monomer 2-methylene-2,3-dihydrothieno (3,4-b) (1,4) dioxine, or 3,4-ethylenedioxythiophene with a exomethylene side group (EDOT-EM). Compared to the previously reported synthesis route, the new strategy uses less steps, with faster reaction rate, and higher yield. The presence of EM group opens up endless possibility for derivatization via either hydro-alkoxy addition or thiol-ene click chemistry. EDOT-EM could be polymerized into stable and low impedance PEDOT-EM polymer using electro-polymerization method on different conducting substrates at both macro and micro scales. Facile post-functionalization of PEDOT-EM with molecules of varying size and functionality (from small molecules to DNAs and proteins) was achieved. The new synthetic route of EDOT-EM and the ease of post-functionalization of PEDOT-EM will greatly accelerate the use of conducting polymer in a broad range of organic electronics and bioelectronics applications.

SUBMITTER: Wu B

PROVIDER: S-EPMC6450363 | biostudies-literature | 2019

REPOSITORIES: biostudies-literature

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Facile Synthesis of a 3,4-Ethylene-Dioxythiophene (EDOT) Derivative for Ease of Bio-Functionalization of the Conducting Polymer PEDOT.

Wu Bingchen B Cao Bin B Taylor Ian Mitch IM Woeppel Kevin K Cui Xinyan Tracy XT

Frontiers in chemistry 20190329

In the pursuit of conducting polymer based bio-functional devices, a cost-effective and high yield synthesis method for a versatile monomer is desired. We report here a new synthesis strategy for a versatile monomer 2-methylene-2,3-dihydrothieno (3,4-b) (1,4) dioxine, or 3,4-ethylenedioxythiophene with a exomethylene side group (EDOT-EM). Compared to the previously reported synthesis route, the new strategy uses less steps, with faster reaction rate, and higher yield. The presence of EM group op ...[more]

PMID: 30984745

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Project description:We describe the synthesis and characterization of bicontinuous cubic poly(3,4-ethylenedioxythiophene) (PEDOT) conducting polymer gels prepared within lyotropic cubic poly(oxyethylene)10 nonylphenol ether (NP-10) templates with Ia3[combining macron]d (gyroid, GYR) symmetry. The chemical polymerization of EDOT monomer in the hydrophobic channels of the NP-10 GYR phase was initiated by AgNO3, a mild oxidant that is activated when exposed to ultraviolet (UV) radiation. The morphology and physical properties of the resulting PEDOT gels were examined as a function of temperature and frequency using optical and electron microscopy, small-angle X-ray scattering (SAXS), dynamic mechanical spectroscopy, and electrochemical impedance spectroscopy (EIS). Microscopy and SAXS results showed that the PEDOT gels remained ordered and stable after the UV-initiated chemical polymerization, confirming the successful templated-synthesis of PEDOT in bicontinuous GYR nanostructures. In comparison to unpolymerized 3,4-ethylenedioxythiophene (EDOT) gel phases, the PEDOT structures had a higher storage modulus, presumably due to the formation of semi-rigid PEDOT-rich nanochannels. Additionally, the storage modulus (G') for PEDOT gels decreased only modestly with increasing temperature, from ?1.2 × 10(5) Pa (10 °C) to ?7 × 10(4) Pa (40 °C), whereas G' for the NP-10 and EDOT gels decreased dramatically, from ?5.0 × 10(4) Pa (10 °C) to ?1.5 × 10(2) Pa (40 °C). EIS revealed that the impedance of the PEDOT gels was smaller than the impedance of EDOT gels at both high frequencies (PEDOT ?10(2) ? and EDOT 2-3 × 10(4) ? at 10(5) Hz) and low frequencies (PEDOT 10(3)-10(5) ? and EDOT ?5 × 10(5) ? at 10(-1) Hz). These results indicated that PEDOT gels were highly ordered, mechanically stable and electrically conductive, and thus should be of interest for applications for which such properties are important, including low impedance and compliant coatings for biomedical electrodes.

Dataset Information

Facile Synthesis of a 3,4-Ethylene-Dioxythiophene (EDOT) Derivative for Ease of Bio-Functionalization of the Conducting Polymer PEDOT.

Publications

Facile Synthesis of a 3,4-Ethylene-Dioxythiophene (EDOT) Derivative for Ease of Bio-Functionalization of the Conducting Polymer PEDOT.

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