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

Mo, Daize; Zhou, Weiqiang; Ma, Xiumei; Xu, Jingkun; Jiang, Fengxing; Zhu, Danhua

doi:10.1016/j.electacta.2014.11.033

Cited by 30 publications

(7 citation statements)

References 65 publications

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“…Three similar conjugated polymers based on PEDOT, containing different alkyl side chains, 177-179, all display similar C pc 's of 132.5, 135.4, and 129.3 F g À1 at 1 A g À1 respectively, and a decrease to 123.6, 112.4, and 108.9 F g À1 at 10 A g À1 . 170 Symmetric SCs were fabricated with low C pc 's of 31.2, 31.8, and 30.2 F g À1 at 0.5 A g À1 for 177, 178, and 179 respectively, with maximum specific energies of 11.1, 11.3 and 10.7 W h kg À1 . These energies exceed those of most commercial SCs.…”

Section: Positive Charge-accepting Materialsmentioning

confidence: 99%

The rise of organic electrode materials for energy storage

et al. 2016

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Organic electrode materials are very attractive for electrochemical energy storage devices because they can be flexible, lightweight, low cost, benign to the environment, and used in a variety of device architectures. They are not mere alternatives to more traditional energy storage materials, rather, they have the potential to lead to disruptive technologies. Although organic electrode materials for energy storage have progressed in recent years, there are still significant challenges to overcome before reaching large-scale commercialization. This review provides an overview of energy storage systems as a whole, the metrics that are used to quantify the performance of electrodes, recent strategies that have been investigated to overcome the challenges associated with organic electrode materials, and the use of computational chemistry to design and study new materials and their properties. Design strategies are examined to overcome issues with capacity/capacitance, device voltage, rate capability, and cycling stability in order to guide future work in the area. The use of low cost materials is highlighted as a direction towards commercial realization.

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Section: Positive Charge-accepting Materialsmentioning

confidence: 99%

The rise of organic electrode materials for energy storage

et al. 2016

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“…This might be due to the formation of new species as an intermediate which indicates the possibility of side reactions in the PQTS12 film. Generally, the negative shift of the oxidation potential suggests the decreased possibility of side reactions that modify the polymer making it more difficult to oxidize . This indicates that the introduction of sulfur induces reactive sites in the PQTS12 film which are responsible for the positive shifts and side reactions during the electrochemical measurement.…”

Section: Resultsmentioning

confidence: 99%

Sensitive and Selective NO₂ Sensing Based on Alkyl- and Alkylthio-Thiophene Polymer Conductance and Conductance Ratio Changes from Differential Chemical Doping

Dailey

Kale

et al. 2017

ACS Appl. Mater. Interfaces

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NO-responsive polymer-based organic field-effect transistors (OFETs) are described, and room-temperature detection with high sensitivity entirely from the semiconductor was achieved. Two thiophene polymers, poly(bisdodecylquaterthiophene) and poly(bisdodecylthioquaterthiophene) (PQT12 and PQTS12, respectively), were used as active layers to detect a concentration at least as low as 1 ppm of NO. The proportional on-current change of OFETs using these polymers reached over 400% for PQTS12, which is among the highest sensitivities reported for a NO-responsive device based on an organic semiconducting film. From measurements of cyclic voltammetry and the electronic characteristics, we found that the introduction of sulfurs into the side chains induces traps in films of the PQTS12 and also decreases domain sizes, both of which could contribute to the higher sensitivity of PQTS12 to NO gas compared with PQT12. The ratio of responses of PQTS12 and PQT12 is higher for exposures to lower concentrations, making this parameter a means of distinguishing responses to low concentrations for extended times from exposures to high concentrations from shorter times. The responses to nonoxidizing vapors were much lower, indicating good selectivity to NO of two polymers. This work demonstrates the capability of increasing selectivity and calibration of OFET sensors by modulating redox and aggregation properties of polymer semiconductors.

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“…However, PEDOT itself is insoluble in common organic solvents so that the polymer is mainly prepared by electrochemical polymerization, which results in difficulty controlling the film composition, thickness, and morphology. These similar drawbacks exist in several works about other polythiophenes containing the EDOT subunit synthesized by electrochemical polymerization. − On the other hand, the high thermoelectric efficiency of PEDOT:PSS can be partly attributed to an ionic Seebeck effect, which is transient and sensitive to humidity, making the output power unstable and complicating the data analysis. , Most importantly, the ionic transport contributes an unsustainable current to an external circuit, which is detrimental to the operation.…”

Section: Introductionmentioning

confidence: 81%

Modification of the Poly(bisdodecylquaterthiophene) Structure for High and Predominantly Nonionic Conductivity with Matched Dopants

et al. 2017

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Four p-type polymers were synthesized by modifying poly(bisdodecylquaterthiophene) (PQT12) to increase oxidizability by p-dopants. A sulfur atom is inserted between the thiophene rings and dodecyl chains, and/or 3,4-ethylenedioxy groups are appended to thiophene rings of PQT12. Doped with NOBF4, PQTS12 (with sulfur in side chains) shows a conductivity of 350 S cm, the highest reported nonionic conductivity among films made from dopant-polymer solutions. Doped with tetrafluorotetracyanoquinodimethane (F4TCNQ), PDTDE12 (with 3,4-ethylenedioxy groups on thiophene rings) shows a conductivity of 140 S cm. The converse combinations of polymer and dopant and formulations using a polymer with both the sulfur and ethylenedioxy modifications showed lower conductivities. The conductivities are stable in air without extrinsic ion contributions associated with PEDOT:PSS that cannot support sustained current or thermoelectric voltage. Efficient charge transfer, tighter π-π stacking, and strong intermolecular coupling are responsible for the conductivity. Values of nontransient Seebeck coefficient and conductivity agree with empirical modeling for materials with these levels of pure hole conductivity; the power factor compares favorably with prior p-type polymers made by the alternative process of immersion of polymer films into dopant solutions. Models and conductivities point to significant mobility increases induced by dopants on the order of 1-5 cm V s, supported by field-effect transistor studies of slightly doped samples. The thermal conductivities were in the range of 0.2-0.5 W m K, typical for conductive polymers. The results point to further enhancements that could be obtained by increasing doped polymer mobilities.

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

Cited by 30 publications

References 65 publications

The rise of organic electrode materials for energy storage

The rise of organic electrode materials for energy storage

Sensitive and Selective NO₂ Sensing Based on Alkyl- and Alkylthio-Thiophene Polymer Conductance and Conductance Ratio Changes from Differential Chemical Doping

Modification of the Poly(bisdodecylquaterthiophene) Structure for High and Predominantly Nonionic Conductivity with Matched Dopants

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

Cited by 30 publications

References 65 publications

The rise of organic electrode materials for energy storage

The rise of organic electrode materials for energy storage

Sensitive and Selective NO2 Sensing Based on Alkyl- and Alkylthio-Thiophene Polymer Conductance and Conductance Ratio Changes from Differential Chemical Doping

Modification of the Poly(bisdodecylquaterthiophene) Structure for High and Predominantly Nonionic Conductivity with Matched Dopants

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Sensitive and Selective NO₂ Sensing Based on Alkyl- and Alkylthio-Thiophene Polymer Conductance and Conductance Ratio Changes from Differential Chemical Doping