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Conducting polyfurans by electropolymerization of oligofurans.

ABSTRACT: Polyfurans have never been established as useful conjugated polymers, as previously they were considered to be inherently unstable and poorly conductive. Here, we show the preparation of stable and conducting polyfuran films by electropolymerization of a series of oligofurans of different chain lengths substituted with alkyl groups. The polyfuran films show good conductivity in the order of 1 S cm^-1, good environmental and electrochemical stabilities, very smooth morphologies (roughness 1-5 nm), long effective conjugation lengths, well-defined spectroelectrochemistry and electro-optical switching (in the Vis-NIR region), and have optical band-gaps in the range of 2.2-2.3 eV. A low oxidation potential needed for polymerization of oligofurans (compared to furan) is a key factor in achievement of improved properties of polyfurans reported in this work. DFT calculations and experiments show that polyfurans are much more rigid than polythiophenes, and alkyl substitution does not disturb backbone planarity and conjugation. The obtained properties of polyfuran films are similar or superior to the properties of electrochemically prepared poly(oligothiophene)s under similar conditions.

SUBMITTER: Sheberla D

PROVIDER: S-EPMC5586207 | biostudies-literature | 2015 Jan

REPOSITORIES: biostudies-literature

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Conducting polyfurans by electropolymerization of oligofurans.

Sheberla Dennis D Patra Snehangshu S Wijsboom Yair H YH Sharma Sagar S Sheynin Yana Y Haj-Yahia Abd-Elrazek AE Barak Adva Hayoun AH Gidron Ori O Bendikov Michael M

Chemical science 20141017 1

Polyfurans have never been established as useful conjugated polymers, as previously they were considered to be inherently unstable and poorly conductive. Here, we show the preparation of stable and conducting polyfuran films by electropolymerization of a series of oligofurans of different chain lengths substituted with alkyl groups. The polyfuran films show good conductivity in the order of 1 S cm<sup>-1</sup>, good environmental and electrochemical stabilities, very smooth morphologies (roughne ...[more]

PMID: 28966762

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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.

Project description:This paper describes an electropolymerization-based on-chip valving system, accomplished by electrosynthesis of conductive polymeric ionic liquid (CPIL) films at selected points within an array of bipolar electrodes (BPEs), in which each of these wireless electrodes spans an IL-aqueous phase boundary. The low viscosity and high hydrophobicity of the CPIL precursor allow it to be patterned by established microfluidic methods. This advancement has the potential to impact microscale analysis because it allows on-demand creation of solid CPIL microstructures at locations specified by microfluidics, phase boundaries, and electrode potentials. To achieve this outcome, an imidazolium-based IL was functionalized with a pyrrole moiety, and the viscosity was tuned by choosing the appropriate counterion to form a CPIL with the desired viscosity, hydrophobicity, and oxidation potential. This monomer species was then introduced into a microfluidic device, which was prefilled with an aqueous buffer solution. The device comprised many parallel microchannels lined with nanoliter-scale chambers. BPEs interconnected the channels such that the BPE tips were each aligned to a chamber opening. The electrodes contacting the outermost channels were connected directly to a power supply and functioned as driving electrodes. The CPIL displaced the buffer in the channels and established a phase boundary at the opening of each chamber, thereby digitizing the aqueous phase. Finally, an alternating square waveform (under mode 1) was applied for 5 min to yield immobilized polymer films at a location defined by the BPE poles. In total, three modes were developed and three corresponding polymer film patterns were formed. Under mode 2, a DC power supply was used to achieve a dissymmetrical polymer film pattern, and, under mode 3, a regional polymer film pattern was formed under an AC potential with a DC offset. Our preliminary results demonstrate that the generated polymer films are immobile and sufficiently thick to seal the chambers at room temperature over the duration of our observation window (50 min), and this seal is maintained even at elevated temperatures that induce partial evaporation of the chamber contents. A key point is that this method is compatible with a preceding step─dielectrophoretic capture of single melanoma cells within the nanoliter-scale chambers.

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Conducting polyfurans by electropolymerization of oligofurans.

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Conducting polyfurans by electropolymerization of oligofurans.

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