Untersuchungen zum anodischen Verhalten von Carbazolen und Indolo[3,2‐b]carbazolen in Acetonitril

Lamm, W.; Pragst, F.; Jugelt, W.

doi:10.1002/prac.19753170616

Cited by 26 publications

(11 citation statements)

References 21 publications

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“…48 The shift of E 1/2 to more positive values of MMPC compared to p-TTA can be attributed to the free electron pair at the nitrogen in the aromatic system of the carbazole unit. 54 The absorption band at 796 nm is assigned to the radical cation MMPC •+ appearing after oxidation of MMPC and is in accordance with the literature (λ max of radical cation =787 nm). 48 The formation of MMPC is an irreversible reaction and therefore consumes original p-TTA-molecules.…”

Section: ' Results and Discussionsupporting

confidence: 88%

Electrochemically Induced Reversible and Irreversible Coupling of Triarylamines

et al. 2011

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The electrochemical coupling and dimerization behavior of the low molecular compounds triphenylamine (TPA) and 9-phenylcarbazole (PHC) in comparison to tri-p-tolylamine (p-TTA) with para-blocked methyl groups has been investigated in detail. In contrast to the unsubstituted radical cations of TPA and PHC, the radical cations of p-TTA are stable in the radical cation state and do not undergo any further coupling reactions. However, we found that the dicationic state of p-TTA does undergo two different competitive reaction pathways: (1) an irreversible intramolecular coupling reaction which leads to phenylcarbazole moieties and (2) a reversible intermolecular dimerization leading to charged σ-dimers. The σ-dimers become decomposed upon discharging at low potentials (E(pc) = -0.97 V vs Fc/Fc(+)) so that the starting monomer p-TTA is partially regenerated. In particular, the reversible dimerization reaction has not been described in literature so far. Polymeric systems containing para-methyl blocked triarylamines in the side chain exhibit similar coupling behavior upon electrochemical doping.

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Section: ' Results and Discussionsupporting

confidence: 88%

Electrochemically Induced Reversible and Irreversible Coupling of Triarylamines

et al. 2011

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“…propanoyl] indole to 22 in an almost quantitative yield and suggested a mechanism involving oxidation of the dimethoxybenzene ring followed by ring closure. The voltammetry of several aminoindoles has been studied recently.29…”

Section: Sainsbury28 Oxidized 3-[3-(34-dimethoxyphenyl)-mentioning

confidence: 99%

Electrochemistry of natural products. 7. Oxidative decarboxylation of some tetrahydro-.beta.-carbolinecarboxylic acids

Bobbitt¹,

Willis²

1980

J. Org. Chem.

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metastable peak observed at m/e 171.5, assigned to Mt -(M -CO)+ + CO (m*,bd m/e 171.5; m*Icaled m/e 171.5); metastable peak observed at m/e 144, assigned to (M -CO)+ -(M -2 CO)+ + CO (m*om m/e 144,m'd m/e 144); 'H NMR (CDC13) 6 11.4 (s, 1 H),8.4-7.3 (m, 7 H). The sample was identified (mass spectrum) by comparison with an authentic sample of 1-hydroxyanthraquinone.Compound 14 was recovered (91%) from treatment with potassamide in ammonia.Reaction of 1 with Sodium Hydrosulfide. The quinone 1 (8.28 g), sodium hydrosulfide (1.68 g), and benzyl alcohol (100 mL) were refluxed for 9 h. When the mixture was cool, the solid (7 g, impure starting material) was filtered off and discarded. The filtrate was concentrated to ca. 10 mL, acetone (30 mL) was added, and the solid was collected. Chromatography (silica gel, benzene) gave 15 (780 mg, 10%) as small orange cubes: mp 326-327 "C, mass spectrum, m/e (relative intensity) 514

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“…In this sense carbazole and its derivatives are of great interest, and they are actively studied due to their use in material science, coordination chemistry, pharmacy, etc. [2][3][4][5][6]. Thus, carbazole derivatives are used as synthons for preparation of luminophores [7], and branched 3,6disubstituted derivatives of carbazole are applied as building blocks for creation of more complex organic molecules [8].…”

mentioning

confidence: 99%