Synthesis and electrochemical capacitive performance of thieno[3,4-b]pyrazine-based Donor-Acceptor type copolymers used as supercapacitor electrode material

Ju, Xiuping; Kong, Lingqian; Zhao, Jinsheng; Bai, Guoyi

doi:10.1016/j.electacta.2017.04.011

Cited by 34 publications

(16 citation statements)

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“…The polymers containing HoT-BSe units had lower E onset potentials compared to the polymers containing HT-BSe units, due to the stronger electron-donating abilities of 3,4-dihexyloxythiphene compared to 3-hexylthiophene, which improved the conjugation effects of the polymers comprising P(HoT-BSe-OC) and P(HoT-BSe-OF) [ 30 , 31 ]. On the other hand, the acyclic side chains of the dioxythiophenes cause steric repulsions along the polymer backbone that decrease the effective conjugation length of the copolymers, which could offset the stronger electron-donating ability of the 3,4-dihexyloxythiphene unit to some extent [ 10 ]. Thus, only slight decreases in the E onset potentials were observed for the 3,4-dihexyloxythiphene-containing polymers (P(HoT-BSe-OC) and P(HoT-BSe-OF)) compared to those of the 3-hexylthiphene-containing polymers (P(HoT-BSe-OC) and P(OoT-BSe-OF)), in spite of the presence of two alkoxy units with strong electron-donating abilities on the 3,4 sites of the thiophene unit in the former kind of polymers.…”

Section: Resultsmentioning

confidence: 99%

“…The alternating distribution of one donor unit and one acceptor unit along a polymer backbone is the basic feature of the donor-acceptor (D-A) theory, which is considered to be the most effective way to reduce the bandgaps of polymers, by promoting intramolecular charge transfers and then improving the resonance effects on the polymer backbone [4,5]. The D-A approach has been widely exploited for the preparation of desirable CPs for industrial or academic applications such as those of electroluminescence devices [6], polymer solar cells [7,8], and memory devices [9], as well as energy storage devices [10]. Besides, a lot of applications of CPs are based on their electrochromic properties, such as energy-saving intelligent windows, nonemissive display devices, glareproof mirrors, and camouflage materials [11].…”

Section: Introductionmentioning

confidence: 99%

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Soluble Electrochromic Polymers Incorporating Benzoselenadiazole and Electron Donor Units (Carbazole or Fluorene): Synthesis and Electronic-Optical Properties

Kong

et al. 2018

Polymers

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A series of π-conjugated polymers containing alternating benzoselenadiazole (BSe)-bi(thiophene derivative)-carbazole or benzoththiadiazole (BSe)-bi(thiophene derivative)-fluorene units were designed and synthesized. Thiophene derivatives, namely 3-hexylthiophene, 3,4-bihexyloxythiophene, and 3,4-bioctyloxythiophene, were used as the π-bridges of the polymers. The polymers were characterized in detail in terms of their thermal stabilities, cyclic voltammograms, UV-Vis absorption, spectroelectrochemistry, dynamic switching property and so forth. The alkoxy thiophene π-bridged polymers have lower onset oxidation potentials and bandgaps than that of their corresponding alkyl thiophene π-bridged polymers. The selection of the donor units between the carbazole and the fluorene units has nearly no effect on the bandgaps and colors as well as the onset oxidation potentials of the polymers. The increase in the length of the side alkyl chains on the thiophene ring caused a slight increase in the polymer bandgap, which may be caused by the space hindrance effect. The dynamic switching abilities of the polymers were obtained by the chronoabsorptometry method, and the results also suggested that the alkoxy thiophene-containing polymers (as π-bridges) have higher contrast ratios than the corresponding alkyl thiophene-containing polymers. Furthermore, the increase in the length of the side alkyl chain might have a detrimental effect on the optical contrast ratios of the polymers.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Soluble Electrochromic Polymers Incorporating Benzoselenadiazole and Electron Donor Units (Carbazole or Fluorene): Synthesis and Electronic-Optical Properties

Kong

et al. 2018

Polymers

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“…c) Capacitance retention of our symmetric (red) and asymmetric (black) supercapacitor. d) Capacitance retention for n-type Faradaic polymers: (1) PMOTP [27] ; (2) pCzAQCz [25] ; (3) PDEQ [41] ; (4) PDDDBT [41] ; (5) PBEDOT-iI. [21] e) Comparison of energy density versus power density for polymer supercapacitors, commercial double-layer supercapacitor [41] (6), and commercial lithium battery [41] (7).…”

Section: Methodsmentioning

confidence: 99%

“…Overall, the aforementioned technologies lead to poor coulombic efficiency and rapid degradation with redox cycling, exhibiting a low capacitance retention of <80% at 1000 cycles. [25,27] Here, we examine a new approach to meet the critical need for stable Faradaic anodes through the use of an open-shell donoracceptor (DA) conjugated polymer (CP) with intrinsic electrical conductivity (σ ≈ 10 −3 S cm −1 ) and enhanced charge delocalization in the reduced state. We recently demonstrated a novel class of DA CPs [28] with very narrow bandgaps and open-shell electronic structures emanating from a high degree of electronic coherence along the conjugated backbone, despite inherent disorder and heterogeneity.…”

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confidence: 99%

Wide Potential Window Supercapacitors Using Open‐Shell Donor–Acceptor Conjugated Polymers with Stable N‐Doped States

Wang

Huang

Eedugurala

et al. 2019

Advanced Energy Materials

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IntroductionSupercapacitors are electrochemical energy storage devices that store charge through fast, reversible redox reactions, enable load-leveling, regenerative energy harvesting, and high power applications. [1][2][3][4][5][6] The energy density of a supercapacitor (E = CV 2 /2) is linearly dependent on the specific capacitance C and proportional to the square of the operational voltage V. The main strategies to increase energy depend upon the mechanism of charge storage, whether capacitive or Faradaic. Capacitive electrodes store charge on the surface; hence, research is focused on strategies to increase the surface area, typically based on high surface area carbons. [7][8][9] Faradaic materials undergo redox reactions and offer the ability to tune the operating voltage. There has been considerable success in tuning the cathode voltage and delivering high capacitance systems operating at the upper limit of prototypical nonaqueous electrolytes. [1,7] However, the device voltage and energy remain limited by a lack of complementary high power electrodes for the anode. [10,11] In the absence of new high voltage electrolytes, there is no room to further extend the cathode potential, because over-potential may lead to hazardous runaway reactions between the highly oxidized cathodes and flammable nonaqueous electrolytes. In contrast, it is generally safe for nonaqueous electrolytes to operate down to −2 V relative to the Ag/AgCl electrode, and the development of anode materials is critical to increase the energy densities of supercapacitors.Consequently, there is an urgent need for strategies aimed at extending the operational voltage toward negative potentials to improve the energy density and cell voltage of supercapacitors. As an alternative to metal oxides, redox-active macromolecules offer mechanical flexibility, low-cost, and scalability relevant for small and large scale applications. [12][13][14][15][16] In radical polymers, [17][18][19][20] the redox sites are at pendant radical groups distributed along a polymer backbone. Due to the insulating nature of the backbone and low conductivity, devices based on these materials require blending with additional conductive materials for electron transport, ultimately lowering the electrode energy Supercapacitors have emerged as an important energy storage technology offering rapid power delivery, fast charging, and long cycle lifetimes. While extending the operational voltage is improving the overall energy and power densities, progress remains hindered by a lack of stable n-type redox-active materials. Here, a new Faradaic electrode material comprised of a narrow bandgap donor−acceptor conjugated polymer is demonstrated, which exhibits an open-shell ground state, intrinsic electrical conductivity, and enhanced charge delocalization in the reduced state. These attributes afford very stable anodes with a coulombic efficiency of 99.6% and that retain 90% capacitance after 2000 charge-discharge cycles, exceeding other n-dopable organic materials. Redox cycling proce...

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“…Commonly used donor units are benzothiophene [ 21 ], fluorene [ 22 ], carbazole [ 23 ], triphenylamine, and cyclopentadithiophene [ 24 ], and so on. Commonly used acceptor units are mainly heterocyclic rings containing O, N, or S, such as pyrrole [ 25 ], pyridine [ 26 ], benzopyrazine [ 9 , 10 , 11 , 12 , 13 ], thienopyrazine [ 27 ], pyridopyrazine [ 28 ], benzothiadiazole [ 29 ], benzotriazole [ 30 ], and phenanthroline [ 31 ] et al Pyrazine is a diazine with two N atoms symmetrically positioned at the one and four positions. Pyrazine has a higher electron affinity than pyridine, which contains only one N atom.…”

Section: Introductionmentioning

confidence: 99%

Effects of Pyrazine Derivatives and Substituted Positions on the Photoelectric Properties and Electromemory Performance of D–A–D Series Compounds

Song

Kong

et al. 2018

Materials

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Pyrazine derivatives quinoxaline and pyridopyrazine were selected as the acceptors, and benzocarbazole was used as the donor to synthesize four different D–A–D compounds. The results showed that 2,3-bis(decyloxy)pyridine[3,4-b]pyrazine (DPP) exhibited stronger electron-withdrawing ability than that of 2,3-bis(decyloxy)quinoxaline (DPx), because DPP possesses one more nitrogen (N) atom, resulting in a red-shift of the intramolecular charge transfer (ICT) absorption bands and fluorescent emission spectra for compounds with DPP as the acceptor compared with those that use DPx as the acceptor. The band-gap energy (Eg) of the four D–A–D compounds were 2.82 eV, 2.70 eV, 2.48 eV, and 2.62 eV, respectively, for BPC-2DPx, BPC-3DPx, BPC-2DPP, and BPC-3DPP. The solvatochromic effect was insignificant when the four compounds were in the ground state, which became significant in an excited state. With increasing solvent polarity, a 30–43 nm red shift was observed in the emissive spectra of the compounds. The thermal decomposition temperatures of the four compounds between 436 and 453 °C had very high thermal stability. Resistor-type memory devices based on BPC-2DPx and BPC-2DPP were fabricated in a simple sandwich configuration, Al/BPC-2DPx/ITO or Al/BPC-2DPP/ITO. The two devices showed a binary non-volatile flash memory, with lower threshold voltages and better repeatability.

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Synthesis and electrochemical capacitive performance of thieno[3,4-b]pyrazine-based Donor-Acceptor type copolymers used as supercapacitor electrode material

Cited by 34 publications

References 50 publications

Soluble Electrochromic Polymers Incorporating Benzoselenadiazole and Electron Donor Units (Carbazole or Fluorene): Synthesis and Electronic-Optical Properties

Soluble Electrochromic Polymers Incorporating Benzoselenadiazole and Electron Donor Units (Carbazole or Fluorene): Synthesis and Electronic-Optical Properties

Wide Potential Window Supercapacitors Using Open‐Shell Donor–Acceptor Conjugated Polymers with Stable N‐Doped States

Effects of Pyrazine Derivatives and Substituted Positions on the Photoelectric Properties and Electromemory Performance of D–A–D Series Compounds

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