Künstliche Organische Farbstoffe und Ihre Zwischenprodukte

Schweizer, Hans Rudolf

doi:10.1007/978-3-642-87245-7

Cited by 59 publications

(18 citation statements)

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“…Pigments absorbing in the near-infrared, at the gallium aluAlthough no structure determination was ever published, the minium arsenide (GaAlAs) or indium phosphide (InP) diode pigment aceanthrene green was reported by chemical laser wavelengths, have become the subject of an increasing Abstract (6), Color Index (7) and other authors (8)(9)(10) as havnumber of studies. For near-infrared piging the 1,6,7, 16-dibenzo[a,o]perylenetetrac~boxylic diimide merits are required for in printing, structure 3.…”

Section: Introductionmentioning

confidence: 99%

Design and synthesis of near-infrared absorbing pigments. II. Structure determination of aceanthrene green and derivatives

Désilets¹,

Kazmaier²,

Burt³

et al. 1995

Can. J. Chem.

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Abstract:The reported structure of aceanthrene green, a pigment prepared by potassium hydroxide fusion of 1.9-anthracenedicarboxylic imide, was found to be incorrect. The structure of the pigment is reassigned to 7,8,15,16-dibenzo[a j]perylenetetracarboxylic diimide on the basis of COSY, NOESY, and inversion-recovery 'H NMR experiments. N-Alkyl-or N-phenyl-l,9-anthracenedicarboxylic imides, aceanthryleno[l,2-blquinoxaline, and a benzimidazole derivative of 1,9-anthracenedicarboxylic anhydride were found to give the same dibenzo[a jlperylene structure when reacted in potassium hydroxide. The electronic spectra of these derivatives is reported and it is shown that, as predicted by Pariser-Parr-Pople calculations, they absorb in the near-infrared. Finally, a mechanistic outline for the fusion is proposed on the basis of AM1 and frontier molecular orbital calculations.Key words: photoconductor, near-infrared, aceanthrene green, alkalifusion, polycyclic aromatic hydrocarbon.RCsumC : On a trouvC que la structure proposCe anterieurement pour l'ackanthrbne vert, un pigment prCparC par fusion de l'imide de l'acide anthracbne-l,9-dicarboxylique avec de l'hydroxyde de potassium, est incorrecte. En se basant sur des expkriences COSY, NOESY et d'inversion-rCcupCration en RMN du 'H on lui a rCattribuC la structure du diimide de l'acide dibenzo[a jlpCrylbne-7,8,15,16-tCtracarboxylique. On a trouvC que par rCaction, par fusion avec de l'hydroxyde de potassium, les N-alkyl-ou N-phCnylimides de l'acide anthrackne-1,9-di-carboxylique, l'acCanthrylCno[l,2-b]quinoxaline et un dCrivC benzimidazole de l'anhydride de l'acide anthracbne-l,9-dicarboxylique conduisent tous B la m&me structure dibenzo[a jlpCrylkne. On rapporte les spectres Clectroniques de ces dCrivCs et il est montrC, tel que prCdit par des calculs de type Pariser-Parr-Pople, qu'ils absorbent dans le proche infrarouge. Enfin, en se basant sur des calculs d'orbitales molCculaires AM1 et frontibres, on propose un aperp du mCcanisme pour la fusion.Mots cles : photoconducteur, proche infrarouge, acCanthrbne vert, fusion alcaline, hydrocarbure polycyclique aromatique.[Traduit par la rCdaction]

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Section: Introductionmentioning

confidence: 99%

Design and synthesis of near-infrared absorbing pigments. II. Structure determination of aceanthrene green and derivatives

Désilets¹,

Kazmaier²,

Burt³

et al. 1995

Can. J. Chem.

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“…Structure and fluorescence of a m dyes along two or three axes and the molecules can exist in different electronic arrangements (Schweizer, 1964;Venkataraman, 1952). However, some general rules of molecular spectroscopy (Kortum et al, 1952) were found pertinent to this study.…”

Section: '4mentioning

confidence: 99%

“…This so-called internal conversion has been lucidly discussed by Barrow (1964). In many dye molecules such internal conversion is much more probable than the change in electronic arrangement necessary for a large energy transfer (Schweizer, 1964;Staab, 1962;Venkataraman, 1952).…”

Section: Energy Of Dye Moleculesmentioning

confidence: 99%

An investigation into the relation between structure and fluorescence of azo dyes

Puchtler

Sweat

Gropp

1967

Journal of the Royal Microscopical Society

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SYNOPSIS Though azo dyes are not fluorescent in solutions, many azo dyes become fluorescent when bound to tissues. This fluorescence is determined largely by the aromatic components of the dye molecules. Like chromophores, these fluorophores are affected by other groupings in dye molecules. Relatively short, compact systems of conjugated double bonds or linking of such resonators by insulating groups favours fluorescence. Long chains of conjugated double bonds and coupling of azo groups in the 1,4‐ or 2,7‐ position of naphthols diminish or abolish fluorescence. Various factors considered important for the fluorescence of other classes of dyes, such as ring closure, coplanarity of chromophores, accumulation of ring systems and low dye concentration are detrimental to the fluorescence of azo dyes. However, these rules apply only to azo dyes; the fluorescence of triphenylmethane, anthraquinone, and quinone‐imine dyes is governed by different factors. Three dioxazine dyes and three copper phthalocyanine dyes included in this study were non‐fluorescent.

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“…In some cases a partial degradation was found for the application of 1 as vat dyes. [5] A protection of the dyes against even a severe attack of alkali would be an appreciable improvement.…”

Section: Introductionmentioning

confidence: 99%

“…[1,4] On the other hand, the persistency of the dyes to bases is not so pronounced. [5,6] Molten KOH and concentrated bleach [7] do not affect the dyes, however, alcoholic alkali causes solvolysis [8] of the imide group and a ring-contraction reaction, [9] respectively. In some cases a partial degradation was found for the application of 1 as vat dyes.…”

Section: Introductionmentioning

confidence: 99%

Perylene Dyes with High Resistance to Alkali

et al. 2005

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The attachment of a γ‐hydroxy alkyl group to a nitrogen atom of perylene‐3,4:9,10‐tetracarboxylic bisimides results in a persistency to alkaline hydrolysis, even to alkali alcoholates. The solubility of these dyes can be controlled by substituents in the β‐position of the alkyl groups so that either highly stable pigments or dyes for homogeneous solutions with high fluorescence quantum yields are obtained. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

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Künstliche Organische Farbstoffe und Ihre Zwischenprodukte

Cited by 59 publications

References 0 publications

Design and synthesis of near-infrared absorbing pigments. II. Structure determination of aceanthrene green and derivatives

Design and synthesis of near-infrared absorbing pigments. II. Structure determination of aceanthrene green and derivatives

An investigation into the relation between structure and fluorescence of azo dyes

Perylene Dyes with High Resistance to Alkali

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