Efficient post-polymerization functionalization of conducting poly(3,4-ethylenedioxythiophene) (PEDOT) via ‘click’-reaction

Bu, Hang-Beom; Götz, Günther; Reinold, Egon; Vogt, Astrid; Schmid, Sylvia; Segura, José L.; Blanco, Raúl; Gómez, Rafael; Bäuerle, Peter

doi:10.1016/j.tet.2010.12.022

Cited by 35 publications

(33 citation statements)

References 84 publications

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“…COOH‐Functionalized EDOT derivatives were synthesized by Yu and co‐workers, and electropolymerized thin PEDOT films exhibited good biocompatibility, very low intrinsic cytotoxicity, and displayed no inflammatory response upon implantation, making them ideal for biosensing and bioengineering applications . 2‐Chloromethyl‐2,3‐dihydrothieno[3,4‐ b ][1,4]dioxine (EDOT‐MeCl), as one of EDOT derivatives, is a versatile intermediate to easily access functionalized EDOT derivatives and their corresponding polymers . By these aspects, we might conjecture that polymerization of EDOT‐MeCl and properties and characterizations of its polymer should be studied and be necessary for the design and development of novel PEDOT derivatives with a variety of excellent properties.…”

Section: Introductionmentioning

confidence: 99%

Electrosynthesis, characterization, and application of poly(3,4‐ethylenedioxythiophene) derivative with a chloromethyl functionality

Zhang

Wen

Yao

et al. 2013

J of Applied Polymer Sci

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Poly(2-chloromethyl-2,3-dihydrothieno [3,4-b][1,4]dioxine), a chloromethyl functionalized poly(3,4-ethylenedioxythiophene) derivative (PEDOT-MeCl), was synthesized electrochemically via the potentiostatic polymerization of its monomer in dichloromethane solution containing suitable tetrabutylammonium tetrafluoroborate, then it was used for the characterization of film properties and the fabrication of electrochemical sensor. The properties of the resulting PEDOT-MeCl film were characterized by different methods such as cyclic voltammetry, electrochemical impedance spectroscopy, Fourier transform infrared and ultraviolet-visible techniques, scanning electron microscope, and thermogravimetric analysis. The PEDOT-MeCl film displayed a good reversible redox activity, remarkable capacitance properties, good thermal stability, rough, and porous structure, especially fluorescent spectra indicated that PEDOT-MeCl was a blue-emitter with maximum emission centered at 396 and 398 nm. Finally, the PEDOT-MeCl film was employed for the fabrication of the sensing electrode, and dopamine was chosen as a model analyte for the application of the electrochemical sensor. Results indicated that the PEDOT-MeCl film as sensing interface was feasible, and studies of these film properties were very beneficial for studying properties and applications of other poly(3,4-ethylenedioxythiophene) derivative films.

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Section: Introductionmentioning

confidence: 99%

Electrosynthesis, characterization, and application of poly(3,4‐ethylenedioxythiophene) derivative with a chloromethyl functionality

Zhang

Wen

Yao

et al. 2013

J of Applied Polymer Sci

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“…These electrodes presented the typical CP shape of p-type semiconductors (Bu et al, 2011). At À 1.03 V (vs. Fc/Fc þ ) the electrografted polymer shifted from a semiconducting to a conducting regime.…”

Section: Preparation and Characterization Of Azido-pedot Electrodesmentioning

confidence: 94%

“…reported the first example of post-functionalization of a novel conducting poly (azidomethyl-EDOT) (azido-PEDOT) by "click" chemistry with various types of terminal alkynes (Bu et al, 2008). Since then, several examples of derivatization of azido-PEDOT with alkyne-containing fluorophores (Daugaard et al, 2008), ferrocene, glycosides, or fullerenes (Bu et al, 2011) have been described. However, to the best of our knowledge, no study has yet applied "click" chemistry to develop label-free DNA hybridization sensors based on conducting PEDOTs.…”

Section: Introductionmentioning

confidence: 99%

Label-free electrochemical DNA sensor using “click”-functionalized PEDOT electrodes

Galán

Prieto‐Simón

Alvira

et al. 2015

Biosensors and Bioelectronics

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Here we describe a label-free electrochemical DNA sensor based on poly(3,4-ethylenedioxythiophene)-modified (PEDOT-modified) electrodes. An acetylene-terminated DNA probe, complementary to a specific "Hepatitis C" virus sequence, was immobilized onto azido-derivatized conducting PEDOT electrodes using "click" chemistry. DNA hybridization was then detected by differential pulse voltammetry, evaluating the changes in the electrochemical properties of the polymer produced by the recognition event. A limit of detection of 0.13 nM was achieved using this highly selective PEDOT-based genosensor, without the need for labeling techniques or microelectrode fabrication processes. These results are promising for the development of label-free and reagentless DNA hybridization sensors based on conducting polymeric substrates. Biosensors can be easily prepared using any DNA sequence containing an alkyne moiety. The data presented here reveal the potential of this DNA sensor for diagnostic applications in the screening of diseases, such as "Hepatitis C", and genetic mutations.

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“…2-(Azidomethyl)-2,3-dihydrothieno[3,4- b ][1,4]dioxine (PEDOT-N 3 ) [ 42 , 63 ] and sodium 3-(prop-2-yn-1-yloxy)propane-1-sulfonate (SO 3 Na–alkyne) [ 64 ] were synthesized based on literature.…”

Section: Methodsmentioning

confidence: 99%

Functionalized branched EDOT-terthiophene copolymer films by electropolymerization and post-polymerization “click”-reactions

Goll¹,

Ruff²,

Muks³

et al. 2015

Beilstein J. Org. Chem.

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SummaryThe electrocopolymerization of 3,4-ethylenedioxythiophene (EDOT) with the branched thiophene building block 2,2′:3′,2″-terthiophene (3T) is presented as a versatile route to functional polymer films. Comparisons to blend systems of the respective homopolymers PEDOT and P3T by in situ spectroelectrochemistry and Raman spectroscopy prove the successful copolymer formation and the access to tailored redox properties and energy levels. The use of EDOT-N3 as co-monomer furthermore allows modifications of the films by polymer analogous reactions. Here, we exemplarily describe the post-functionalization with ionic moieties by 1,3-dipolar cycloaddition (“click”-chemistry) which allows to tune the surface polarity of the copolymer films from water contact angles of 140° down to 40°.

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Efficient post-polymerization functionalization of conducting poly(3,4-ethylenedioxythiophene) (PEDOT) via ‘click’-reaction

Cited by 35 publications

References 84 publications

Electrosynthesis, characterization, and application of poly(3,4‐ethylenedioxythiophene) derivative with a chloromethyl functionality

Electrosynthesis, characterization, and application of poly(3,4‐ethylenedioxythiophene) derivative with a chloromethyl functionality

Label-free electrochemical DNA sensor using “click”-functionalized PEDOT electrodes

Functionalized branched EDOT-terthiophene copolymer films by electropolymerization and post-polymerization “click”-reactions

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