Systematic study on chemical oxidative and solid‐state polymerization of poly(3,4‐ethylenedithiathiophene)

Abstract

Systematic research on the synthesis, chemical oxidative polymerization of 3,4‐ethylenedithiathiophene (EDTT) in the presence of surfactants or not, and solid‐state polymerization of 2,5‐dibromo‐3,4‐ethylenedithiathiophene (DBEDTT) and 2,5‐diiodo‐3,4‐ethylenedithiathiophene (DIEDTT) under solventless and oxidant‐free conditions has been investigated. Effects of oxidants (Fe3+ salts, persulfate salts, peroxides, and Ce4+ salts), solvents (H2O, CH3CN/H2O, and CH3CN), surfactants, and so forth on polymerization reactions and properties of poly(3,4‐ethylenedithiathiophene) (PEDTT) were discussed. Characterizations indicated that FeCl3 was more suitable oxidant for oxidative polymerization of EDTT, while CH3CN was a better solvent to form PEDTT powders with higher yields and electrical conductivities. Dispersing these powders in aqueous polystyrene sulfonic acid (PSSH) solution showed better stability and film‐forming property than sodium dodecylsulfate and sodium dodecyl benzene sulfonate. Oxidative polymerization of EDTT in aqueous PSSH solutions formed the solution processable PEDTT dispersions with good storing stability and film‐forming performance. Solvent treatment showed indistinctive effect on electrical conductivity of free‐standing PEDTT films. As‐formed PEDTT synthesized from solid‐state polymerization showed similar electrical conductivity, poorer stability, but better thermoelectric property than oxidative polymerization. Contrastingly, PEDTT synthesized from DIEDTT showed higher electrical conductivity (0.18 S cm−1) than DBEDTT which showed better thermoelectric property with higher power factor value (6.7 × 10−9 W m−1 K−2). © 2012 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2012

Self-Assembly of Perylene Imide Molecules into 1D Nanostructures: Methods, Morphologies, and Applications

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Preparation and characterization of aqueous dispersions of poly(3,4‐ethylenedithiathiophene‐co‐3,4‐ethylenedioxythiophene)/ poly(styrene sulfonate) and their conducting films

“…In the past 20 years, the electrochemical homopolymerization of compounds containing 3,4‐ethylenedithiathiophene (EDTT) units, as listed in Scheme , has been studied in detail 6, 9–11, 16, 18, 20, 22. Other methods, such as chemical oxidative and solid‐state homopolymerization and, recently, Stille coupling, have also been reported 4, 7, 23–26. However, PEDTT and its derivatives achieved from these methods are usually powders.…”

Alkyl functionalized bithiophene end-capped with 3,4-ethylenedioxythiophene units: synthesis, electropolymerization and the capacitive properties of their polymers

“…Among the ECPs, poly (3,4-ethylenedioxythiophene) (PEDOT) is a good candidate for supercapacitor due to its good environmental and thermal stability, high conductivity, and excellent electrochemical stability at broader voltage window relative to polyaniline and polypyrrole [9,10]. Compared with other ECPs, however, its moderate specific capacitance suggests that there is a need to develop new alternatives [11].…”