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Functionalized branched EDOT-terthiophene copolymer films by electropolymerization and post-polymerization "click"-reactions.

ABSTRACT: The 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°.

SUBMITTER: Goll M

PROVIDER: S-EPMC4362086 | biostudies-literature | 2015

REPOSITORIES: biostudies-literature

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Functionalized branched EDOT-terthiophene copolymer films by electropolymerization and post-polymerization "click"-reactions.

Goll Miriam M Ruff Adrian A Muks Erna E Goerigk Felix F Omiecienski Beatrice B Ruff Ines I González-Cano Rafael C RC Lopez Navarrete Juan T JT Ruiz Delgado M Carmen MC Ludwigs Sabine S

Beilstein journal of organic chemistry 20150311

The 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 modification ...[more]

PMID: 25815088

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Project description:Intrinsically conducting polymers (ICPs) have been widely utilized in organic electronics, actuators, electrochromic devices, and sensors. Many potential applications demand the formation of thin polymer films, which can be generated by electrochemical polymerization. Electrochemical methods are quite powerful and versatile and can be utilized for investigation of ICPs, both for educational purposes and materials chemistry research. In this study, we show that potentiodynamic and potentiostatic techniques can be utilized for generating and characterizing thin polymer films under the context of educational chemistry research and state-of-the-art polymer research. First, two well-known bifunctional monomers (with only two linking sites)-aniline and bithiophene-and their respective ICPs-polyaniline (PANI) and polybithiophene (PBTh)-were electrochemically generated and characterized. Tests with simple electrochromic devices based on PANI and PBTh were carried out at different doping levels, where changes in the UV-VIS absorption spectra and color were ascribed to changes in the polymer structures. These experiments may attract students' interest in the electrochemical polymerization of ICPs as doping/dedoping processes can be easily understood from observable color changes to the naked eye, as shown for the two polymers. Second, two new carbazole-based multifunctional monomers (with three or more linking sites)-tris(4-(carbazol-9-yl)phenyl)silanol (TPTCzSiOH) and tris(3,5-di(carbazol-9-yl)phenyl)silanol (TPHxCzSiOH)-were synthesized to produce thin films of cross-linked polymer networks by electropolymerization. These thin polymer films were characterized by electrochemical quartz crystal microbalance (EQCM) experiments and nitrogen sorption, and the results showed a microporous nature with high specific surface areas up to 930 m2g-1. PTPHxCzSiOH-modified glassy carbon electrodes showed an enhanced electrochemical response to nitrobenzene as prototypical nitroaromatic compound compared to unmodified glassy carbon electrodes.

Dataset Information

Functionalized branched EDOT-terthiophene copolymer films by electropolymerization and post-polymerization "click"-reactions.

Publications

Functionalized branched EDOT-terthiophene copolymer films by electropolymerization and post-polymerization "click"-reactions.

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