Synthesis and characterization of 3-(4-fluorophenyl)thieno[3,2-b]thiophene and 3,3’-(4- fluorophenyl)dithieno[3,2-b;2’,3’-d]thiophene molecules

Topal, Sema; Ulukan, Pelin; Ustamehmetoğlu, Belkıs; Öztürk, Turan; Sezer, Esma

doi:10.1016/j.electacta.2021.138837

Cited by 11 publications

(24 citation statements)

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“…Structural Description of Py-Q, Th-Q, and DTh-Q. Py-Q, Th-Q, and DTh-Q were characterized by 1 H NMR, 13 C NMR, FT-IR, and ESI-HRMS (Figures S1-S6). In order to further visualize their structure, suitable single crystals were cultured through recrystallization and their crystal structures were determined by X-ray single-crystal diffraction.…”

Section: Resultsmentioning

confidence: 99%

“…All reagents and chemicals were purchased from Energy Chemical, Klamar or Macklin Biochemical Co., Ltd., and were used directly as received. 1 H NMR and 13 C NMR spectra were acquired on a Bruker Ascend 400 (400 MHz) spectrometer. FT-IR spectra were obtained on a Bruker INVENIO Fourier transform infrared spectrometer using KBr pellets.…”

Section: Methodsmentioning

confidence: 99%

“…Substituting thiophene unit at 3-position with phenyl, alkoxyl, and ethyl groups has been reported to enhance the stability [11]. Further enhancement in the stability has been achieved through adding electron withdrawing groups to these substituents, like poly (3,4-ethylenedioxythiophene) [12] and poly(3-(4-fluorophenyl)thiophene) [13]. Therefore, structural design of the thiophene-based molecules as monomer offers the route to prepare stable substituted polythiophene as electrode material for supercapacitors.…”

Section: Introductionmentioning

confidence: 99%

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Thiophene or Pyridine-Substituted Quinoline Derivatives: Synthesis, Properties, and Electropolymerization for Energy Storage

Wang

Yao

Shao

et al. 2023

International Journal of Energy Research

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Designing novel electropolymerizable monomers is essential in developing electron donor-electron acceptor (D-A) type conjugated polymers for applications in sensing, catalysis, and energy storage. Thiophene and pyridine-substituted quinoline-based molecules (Th-Q, DTh-Q, and Py-Q) are synthesized in this work, and their crystal structures, optical properties, and electrochemical properties are investigated. The potentiostatic electropolymerization of these molecules are successfully carried out on carbon cloth substrate, with the thiophene and quinoline as the possible electropolymerizable units. The PTh-Q shows the best charge storage performance ( 1.12 × 10 − 3 C at 0.02 mA cm-2 in the potential range of 0-1 V) in 0.1 M Na2SO4, and maintains 77% of the initial capacity after 3000 charge-discharge cycles at 0.02 mA cm-2. The morphology and structure of the PTh-Q does not alter significantly after the repetitive charge-discharge cycling. The superior charge storage performance of the PTh-Q than PDTh-Q and PPy-Q is originated from the exposed highest amount of electrochemically active sites and the participation of redox processes of both hydroxyl/ketone structures on quinoline and thiophene groups.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Thiophene or Pyridine-Substituted Quinoline Derivatives: Synthesis, Properties, and Electropolymerization for Energy Storage

Wang

Yao

Shao

et al. 2023

International Journal of Energy Research

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“…Conducting polymers are among the best candidates for both electrochromic and energy storage applications as their bandgap and optical properties can be optimized by introducing units having different electroactivity and planarity 3,4 . Thiophenes (Th), thienothiophenes (TT), and dithienothiophenes (DTT) are widely used organic heterocyclic molecules in various organic electronic applications including OLEDs, organic solar cells, electrochromic devices, and capacitors due to their electron‐rich structures arising from the presence of electron rich sulfur atoms 5‐11 . On the other hand, PEDOT is commonly used in organic electronics as it provides high conductivity, low oxidation point, high stability in the oxidized state, and high contrast 8,12‐14 .…”

Section: Introductionmentioning

confidence: 99%

“…3,4 Thiophenes (Th), thienothiophenes (TT), and dithienothiophenes (DTT) are widely used organic heterocyclic molecules in various organic electronic applications including OLEDs, organic solar cells, electrochromic devices, and capacitors due to their electron-rich structures arising from the presence of electron rich sulfur atoms. [5][6][7][8][9][10][11] On the other hand, PEDOT is commonly used in organic electronics as it provides high conductivity, low oxidation point, high stability in the oxidized state, and high contrast. 8,[12][13][14] Moreover, PEDOT with adjustable conductivities could be obtained applying well-known synthetic methods such as in situ oxidative polymerization, electropolymerization and transition metal catalyzed coupling polymerization, among which electropolymerization offers tunable conductivity, film morphology and mechanical properties.…”

Section: Introductionmentioning

confidence: 99%

Smart copolymers of ditriphenylaminedithienothiophene with ethylenedioxythiophene for multicolor energy storage systems

Topal

Karakaya

Sezer

et al. 2022

Intl J of Energy Research

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Summary Energy storage materials, having multifunctional properties, are particularly important for the development of intelligent power systems. In this study, conjugated monomers 4′,4′‐(dithieno[3,2‐b:2′,3′‐d]thiophene‐3,5‐diyl)bis(N,N‐diphenyl‐[1,1′‐biphenyl]‐4‐amine) (DTTpTPA, D) and 3,4‐ethylenedioxythiophene (EDOT, E) were electrocopolymerized on ITO surface in different mole ratios. The copolymer films were investigated in terms of energy storage, electrochromic properties and surface morphology. Inclusion of EDOT units into the polymer chain made a significant impact on the energy storage and electrochromic properties of the resultant copolymers. The P(D1‐1E) film, which was obtained at a mole ratio of nD/nE = 1/1, showed the best capacitance value of 22 mF cm−2. All the copolymers displayed a wide range of color change during their redox processes. The best coloration efficiency value of 196 C−1 cm2 was obtained with P(D10‐1E) film, having multi‐electrochromic property of red, green, gray and blue colors. A symmetric solid‐state energy storage device of P(D1‐1E) exhibited a capacitance of 6.58 mF cm−2 with high energy and high‐power density, which proved that P(D1‐1E) is a good candidate for energy storage applications.

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Non‐planar polyimides with monomer containing four triphenylamines for near‐infrared electrochromism and TNP detection

Xia

Zhai

et al. 2023

J of Applied Polymer Sci

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By using triphenylamine (TPA) with a propeller structure connected to the planar fluorene unit as monomer, three novel polyimide (PI)s were prepared through chemical imidization of N,N′‐(9,9‐bis(4‐(diphenylamino) phenyl)‐9H‐fluorene‐2,7‐diyl)‐bis(N‐(4‐methoxyphenyl) benzene‐1,4‐diamine) (TPAF‐NH2) with three kinds of dianhydrides. The three dimensional configurations are designed to decrease molecular stacking rising from strong imide bond, and for faster ion transport in cavity of PIs. All the three PIs have good performance of electrochromic(EC) and sensor. With the voltage increasing from 0 to 1.2 V, the color of P2 film changes from original yellow to red to blue with the response time of only 2.3 s (colored time [tc]) and 2.8 s (bleached time [tb]). The coloring efficiency (CE) of P2 reaches 310 cm2 C−1, with optical contrast (ΔT) of 54%. Especially, the electroactivity of P3 does not decrease significantly after 6000 s cycle. Additionally, there are dual‐band in near‐infrared (NIR) area after the PI being oxidized. P1 with photoluminescence (PL) quantum efficiency (φPL) of 48% can detect trinitrophenol (TNP) effectively. The novel PIs have promising prospect in NIR EC and TNP detection devices.

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Synthesis and characterization of 3-(4-fluorophenyl)thieno[3,2-b]thiophene and 3,3’-(4- fluorophenyl)dithieno[3,2-b;2’,3’-d]thiophene molecules

Cited by 11 publications

References 50 publications

Thiophene or Pyridine-Substituted Quinoline Derivatives: Synthesis, Properties, and Electropolymerization for Energy Storage

Thiophene or Pyridine-Substituted Quinoline Derivatives: Synthesis, Properties, and Electropolymerization for Energy Storage

Smart copolymers of ditriphenylaminedithienothiophene with ethylenedioxythiophene for multicolor energy storage systems

Non‐planar polyimides with monomer containing four triphenylamines for near‐infrared electrochromism and TNP detection

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