Electrochemical behavior of conjugated quinoxaline derivatives

Wang, Rong; Ramaraj, Ramasamy; Okajima, Takaharu; Kitamura, Fusao; Matsumoto, Naoki; Thiemann, Thies; Mataka, Shuntarō; Ohsaka, Takeo

doi:10.1016/j.jelechem.2003.12.016

Cited by 10 publications

(7 citation statements)

References 28 publications

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“…11, which implies that the quinoxaline redox mechanism involved H + . Similar results of pH dependent redox potentials for quinoxaline derivatives were observed in buffered aqueous experiments [29,32,33] and in a study of quinoxaline voltammetry in DMF / water-mixed acidic media [45].…”

Section: Discussionsupporting

confidence: 78%

Voltammetry study of quinoxaline in aqueous electrolytes

Milshtein

Liou

et al. 2015

Electrochimica Acta

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Section: Discussionsupporting

confidence: 78%

Voltammetry study of quinoxaline in aqueous electrolytes

Milshtein

Liou

et al. 2015

Electrochimica Acta

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“…The cation radical then experiences a one-electron one-proton process. Recently, we have calculated the formation energies of possible reduction intermediates of HAT by the MOPAC PM3 method, 40 and results suggested that the pyrazine rings in HAT may be reduced ring by ring. Therefore, when two electrons and three protons are added into HAT, one of the pyrazine rings in HAT is changed to a 1,4-dihydropyrazinium ion.…”

Section: Resultsmentioning

confidence: 99%

Cyclic and Normal Pulse Voltammetric Studies of 2,3,6,7,10,11-Hexaphenylhexazatriphenylene Using a Benzonitrile Thin Layer-Coated Glassy Carbon Electrode

et al. 2003

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The method of interposing a thin layer of immiscible organic solvent (benzonitrile, BN) between a glassy carbon electrode surface and an aqueous solution has been successfully applied to study the electrode reaction of a highly hydrophobic organic molecule, 2,3,6,7,10,11-hexaphenylhexazatriphenylene (HAT). Four couples of well-defined redox peaks of HAT were observed at the BN thin layer-coated electrode in N 2 -saturated 2 M HClO 4 aqueous solution. By cyclic voltammetry, square-wave voltammetry, and normal pulse voltammetry, the thermodynamic and kinetic parameters (i.e., the formal potential, standard rate constant, and cathodic transfer coefficient) for the multistep redox reaction of HAT and its diffusion coefficient were evaluated. The good agreement between the observed normal pulse voltammograms and the calculated one with use of the obtained kinetic and thermodynamic parameters demonstrated that the evaluated parameters are reasonable and that the present approach is useful in the kinetic study of the multistep redox reaction of hydrophobic reactants. A probable reaction mechanism for the whole redox reaction of HAT was also proposed.

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“…The synthetic route toward monomer and polymer are shown in Schemes 1 and 2. [1,2,5] thiadiazole (1) Benzo[c] [1,2,5] thiadiazole (5.0 g, 37 mmol) was introduced into a three-necked flask charged with a stirring bar. HBr (48%, 90 mL) was added and the solution was heated.…”

Section: Generalmentioning

confidence: 99%

“…Quinoxaline (Qx) and its derivatives are promising materials due to their flat and rigid conjugated structures, and their easy structural modification by attaching various side chains which allows to finely tune their optical properties. Quinoxaline based polymers are widely employed in many fields of applications such as organic solar cells (OSCs), dyes or as ligands in luminescent materials or for metal complication in catalysis [1][2][3]. The syntheses of quinoxaline monomers or polymers are quite straight forward and usually result in high yields.…”

Section: Introductionmentioning

confidence: 99%

Tuning molecular energy levels and band gap of two-dimensional benzo[1,2-b:4,5-b′] dithiophene and quinoxaline bearing polymers

Yaşa

Goker

Udum

et al. 2019

Journal of Electroanalytical Chemistry

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Two novel donor-acceptor (D-A)-type two-dimensional (2-D) polymers of PBDTSeQ (P1) and PBDTFQ (P2) were synthesized and characterized where 4,8-bis[5-(2-ethylhexyl) thiophen-2-yl] benzo[1,2-b:4,5-b'] dithiophene (BDT) was used as the donor unit. 2,3-Bis(3,4-bis(octyloxy)phenyl)-5,8-dibromoquinoxaline was used as the acceptor moiety and selenophene and furan were utilized as π bridges. Optoelectronic properties of the polymers were examined by electrochemical and spectroelectrochemical characterizations. In cyclic voltammetry (CV) studies, both polymers were found to be ambipolar. In anodic region, oxidation potentials were observed as 1.45 V and 1.15 V for P1 and P2 respectively, while reduction potentials were 0.65 V and 0.92 V. In cathodic region, redox potentials were found to be −1.36 V/−1.32 V and −2.0 V/−1.51 V for P1 and −1.45 V/ −1.05 V and −2.15 V/−1.45 V for P2. Both polymers showed good solubility in common solvents. The synthesized polymers were used as photoactive layers in solar cell devices.

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Electrochemical behavior of conjugated quinoxaline derivatives

Cited by 10 publications

References 28 publications

Voltammetry study of quinoxaline in aqueous electrolytes

Voltammetry study of quinoxaline in aqueous electrolytes

Cyclic and Normal Pulse Voltammetric Studies of 2,3,6,7,10,11-Hexaphenylhexazatriphenylene Using a Benzonitrile Thin Layer-Coated Glassy Carbon Electrode

Tuning molecular energy levels and band gap of two-dimensional benzo[1,2-b:4,5-b′] dithiophene and quinoxaline bearing polymers

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