Monatshefte für Chemie / Chemical Monthly

, Volume 108, Issue 5, pp 1113–1130 | Cite as

Beiträge zur Chemie der Pyrrolpigmente, 18. Mitt.: Pyrromethenone—Partialstrukturen von Gallenpigmenten: Struktur und Eigenschaften in Lösung

  • Heinz Falk
  • Karl Grubmayr
  • Günther Höllbacher
  • Otmar Hofer
  • Alfred Leodolter
  • Franz Neufingerl
  • Jose M. Ribó
Organische Chemie und Biochemie
Received:

On the chemistry of pyrrole pigments, XVIII.: Pyromethenones — Partial structures of bile pigments: Structures and properties in solution

Abstract

Depending on solvent polarity and concentration a monomer—dimer equilibrium for pyrromethenones was deduced by means of absorption and fluorescence spectroscopy and measurement of a colligative property. The monomer could be characterized as asyn-(Z) form with a dihedral angle at the methine single bond of about fourty degrees using the lanthanide shift technique and nuclearOverhauser effect studies. Two types of dimer geometry with differing bond strengths were found by comparingPPP calculation results with the measured absorption spectra and the liquid crystal induced circular dichroism.

The (Z) isomers can be transformed to the corresponding (E) isomers by means of a photoreaction. The latter is thermally stable but rather sensitive against oxygen, light and protons, an effect which varies strongly with the substitution pattern of the pyrrole fragment thus enabling isolation in certain cases only.

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Copyright information

© Springer-Verlag 1977

Authors and Affiliations

  • Heinz Falk
    • 1
  • Karl Grubmayr
    • 1
  • Günther Höllbacher
    • 1
  • Otmar Hofer
    • 1
  • Alfred Leodolter
    • 1
  • Franz Neufingerl
    • 1
  • Jose M. Ribó
    • 1
  1. 1.Institut für Organische ChemieUniversität WienWienÖsterreich

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