Über die Konstitution der sogen. aromatischen ortho‐Oxy‐azo‐verbindungen

Burawoy, A.; Markowitsch, I.

doi:10.1002/jlac.19335030110

Justus Liebigs Ann. Chem.

1933

DOI: 10.1002/jlac.19335030110

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Über die Konstitution der sogen. aromatischen ortho‐Oxy‐azo‐verbindungen

A. Burawoy

I. Markowitsch

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1936

2003

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Cited by 14 publications

References 40 publications

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Novel Chromogenic Esters of ortho‐Phenylazonaphthols

Kocher¹,

Weder²,

Smith³

2003

Adv Funct Materials

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We have prepared the photo‐labile benzoic acid esters and the acid‐labile tert‐butoxycarbonyl esters of Sudan I and Sudan Red B, two representatives of the ortho‐phenylazonaphthol dye family, exhibiting hydroxyazo–hydrazone tautomerism with the hydrazone as the strongly favored form. The chromophores obtained are “locked” in an exclusive azo configuration and exhibit absorbance spectra which are dramatically blue‐shifted (more than 100 nm) and have strongly reduced extinction coefficients when compared to their parent chromophores. Thus, the esters of the orange dye Sudan I exhibit an absorption maximum in the ultraviolet (UV) regime, and the esters of the red dye Sudan Red B appear yellow. Depending on the nature of the ester moiety, by irradiation with UV light or by exposure to preferentially photochemically released acidic species at elevated temperatures, these esters can be reverted to the parent, highly tinctured Sudan I and Sudan Red B, respectively. Unlike conventional chromogenic systems, these dyes are compatible with melt‐processible polymers and do not require any wet‐chemical development. In polymer films comprised of these chromogenic dyes, color patterns can be produced directly by masked irradiation. We here report on the synthesis, spectral properties, and conversion kinetics of these novel chromogenic dyes, which may be potentially suitable for marking and labeling goods in a lithographic process and for optical data storage and sensing applications.

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Novel Chromogenic Esters of ortho‐Phenylazonaphthols

Kocher¹,

Weder²,

Smith³

2003

Adv Funct Materials

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Innere Komplexverbindungen in der Farbenchemie

Pfitzner¹

1950

Angewandte Chemie

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In den letzten 3 Jahrzehnten sind zahlreiche rnetallhaltige Farbstoffe entwickelt warden. Weltere wertvolle Produkte sind auf dem vlelgestaltigen und verzweigten Gebiet zu erwarten. Es wird eln Uberblick Uber Aufbau, Eigenschaften und Verwendung gegeben. ,,Beizenriehendegg FarbstoffeDie Verwendung von Metallsalzen zur Verbesserung bestirnrnter Farbungen ist alt. Je nach dem benutzten Metall konnten mit ein und demselben Farbstoff ganz verschiedene FarbtUne erzielt werden, was die Vermutung nahelegte, da6 mischen beiden nicht nur einfache Salzbildung eintritt. Welche konstitutionellen Vorbedingungen miissen gegeben sein, damit eine solche Bindung eintritt? Liebermann und Kostaneckil) kamen zuerst zu bestimmten Anschauungen, aber es blieb Alfred Wernerg) vorbehalten, zum ersten Male in klarer Formulierung zum Ausdruck z t~ bringen, dab nur solche Farbstoffe ,,beizenziehend" sind, die die Fahigkeit zur Bildung ,,innerer Komplexsalze" besitzen. Er stellte festg), daB dabei vorzugsweise 5-und 6-giiedrige .Ringe entstehen. Der Begriff der ,,inneren Yornplexsalze" geht auf Leya) zuriick. 0 ) Vgl. A. Bureway u.

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Versuche in der 2‐Aminopyridinreihe V. Untersuchungen über die Reaktionsfähigkeit der Aminogruppe in 2‐Methyl‐6‐aminopyridin

Feist

Kuklinski

1936

Archiv der Pharmazie

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Über die Konstitution der sogen. aromatischen ortho‐Oxy‐azo‐verbindungen

Cited by 14 publications

References 40 publications

Novel Chromogenic Esters of ortho‐Phenylazonaphthols

Novel Chromogenic Esters of ortho‐Phenylazonaphthols

Innere Komplexverbindungen in der Farbenchemie

Versuche in der 2‐Aminopyridinreihe V. Untersuchungen über die Reaktionsfähigkeit der Aminogruppe in 2‐Methyl‐6‐aminopyridin

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