Electrochemistry of some novel hole transport materials

Russell, Dale D.; Meyer, R. J.; Jubran, Nusrallah; Tokarski, Zbigniew; Moudry, Ron; Law, Kam Wah

doi:10.1016/j.jelechem.2003.12.012

Cited by 5 publications

(3 citation statements)

References 7 publications

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“…The first and second oxidation peaks would be identified as consecutive electron-transfer reactions to form the dication. A similar process has been proposed for organic materials with two carbazole moieties . The CV analyses of furan-based heteroacenes 3 and 16a gave quasi-reversible wave ( E ox peak vs Ag/Ag + ; 1.59 V for 3 , 1.39 and 1.62 V for 16a ), whereas that of 16b showed a reversible wave (1.64 V vs Ag/Ag + ) at the scan rate between 30 and 100 mV·s -1 (Figure d−f).…”

Section: Resultssupporting

confidence: 74%

“…A similar process has been proposed for organic materials with two carbazole moieties. 43 The CV analyses of furan-based heteroacenes 3 and 16a gave quasi-reversible wave (E ox peak vs Ag/Ag + ; 1.59 V for 3, 1.39 and 1.62 V for 16a), whereas that of 16b showed a reversible wave (1.64 V vs Ag/Ag + ) at the scan rate between 30 and 100 mV‚s -1 (Figure 3d-f). Two oxidation waves of 16a indicate the dication formation, similar to pyrrole-based heteroacenes.…”

Section: Syntheticmentioning

confidence: 93%

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Synthesis of Ladder-Type π-Conjugated Heteroacenes via Palladium-Catalyzed Double N-Arylation and Intramolecular O-Arylation

2007

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Ladder-type heteroacenes containing pyrrole or furan rings, indolo[3,2-b]carbazoles and dibenzo[d,d']benzo[1,2-b:4,5-b']difurans, were effectively synthesized from the common intermediates, 2,5-bis(o-chloroaryl)hydroquinones. The key reactions are palladium-catalyzed double N-arylation of aniline and intramolecular O-arylation, which enable regioselective ring closure. In addition to the parent indolo[3,2-b]carbazole and dibenzo[d,d']benzo[1,2-b:4,5-b']difuran, their derivatives with an alkyl or cyano group were first synthesized. Photophysical and electrochemical studies showed that the obtained heteroacenes have lower HOMO energy levels and larger band gaps than the corresponding hydrocarbon acene, pentacene. An X-ray analysis of dibenzo[d,d']benzo[1,2-b:4,5-b']difuran revealed that it was packed in herringbone fashion.

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Section: Resultssupporting

confidence: 74%

Section: Syntheticmentioning

confidence: 93%

Synthesis of Ladder-Type π-Conjugated Heteroacenes via Palladium-Catalyzed Double N-Arylation and Intramolecular O-Arylation

2007

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“…In addition, the application of fundamental electrochemical methods to survey the oxidative behavior of materials with inherent hole-transport properties can be extremely useful. 13 Using voltammetric techniques such as CV, it is feasible to elucidate features such as the number of electron transfer processes involved in the redox steps, the active sites present in the skeleton's molecule, and their kinetic and thermodynamic properties, among other practical data as the estimation of optical bandgaps. 14,15 Indeed, the electrochemical characterization of m-MTDATA has been carried out yet in solution.…”

Section: Introductionmentioning

confidence: 99%

Electroactivity of a starburst hole-transport material in Langmuir–Blodgett films. Solid state effects and intervalence charge transfer

Parra

Caño

Rodrı́guez-Méndez

et al. 2007

Phys. Chem. Chem. Phys.

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Here we report on the electroactivity properties of Langmuir-Blodgett (LB) films of the hole-transport molecule 4,4',4''-tris[3-methylphenyl(phenyl)amino] triphenylamine (m-MTDATA). Fairly stable Langmuir films at the air-water interface are accomplished, despite the non-amphiphilic character of the molecule. The reflection-absorption infrared spectroscopy (RAIRS) and Fourier transform infrared (FT-IR) analysis revealed that the molecules arrange with no neat preferential orientation, in agreement with the amorphous glassy nature of this starburst molecule. However, there is a tendency of the molecules to organize in a more planar conformation due to the intermolecular stacking induced by the LB technique. On the other hand, the fundamental electrochemistry (by cyclic voltammetry, CV) of the films is also analyzed. The CV studies of both solution and films reveal that both the solid state and the electrolyte's anions clearly affect the m-MTDATA's electroactivity, exhibiting a unique and broad redox process instead of the two reversible oxidations observed in solution. The oxidization mechanism is discussed. Finally, the spectroelectrochemistry studies evidence that the oxidization of the films leads to new absorption bands, among which the emerging bands in the NIR region ascribed to intervalence charge transfer (IVCT) between the generated aminyl radical cations should be pointed out.

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The mixed carbon–nitrogen conjugation in the carbazole based polymer; the electrochemical, UVVis, EPR, and IR studies on 1,4 bis[(E)2-(9H-carbazol-9-yl)vinyl]benzene

Łapkowski

Żak

Karoń

et al. 2011

Electrochimica Acta

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Electrochemistry of some novel hole transport materials

Cited by 5 publications

References 7 publications

Synthesis of Ladder-Type π-Conjugated Heteroacenes via Palladium-Catalyzed Double N-Arylation and Intramolecular O-Arylation

Synthesis of Ladder-Type π-Conjugated Heteroacenes via Palladium-Catalyzed Double N-Arylation and Intramolecular O-Arylation

Electroactivity of a starburst hole-transport material in Langmuir–Blodgett films. Solid state effects and intervalence charge transfer

The mixed carbon–nitrogen conjugation in the carbazole based polymer; the electrochemical, UVVis, EPR, and IR studies on 1,4 bis[(E)2-(9H-carbazol-9-yl)vinyl]benzene

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