Synthesis of perylene-3,4-dicarboximides — Novel highly photostable fluorescent dyes

Authors

  • Leonhard Feiler,

    1. Institut für Organische Chemie der Universität München, Karlstraße 23, D-80333 München, Germany
    Search for more papers by this author
  • Heinz Langhals,

    Corresponding author
    1. Institut für Organische Chemie der Universität München, Karlstraße 23, D-80333 München, Germany
    • Institut für Organische Chemie der Universität München, Karlstraße 23, D-80333 München, Germany
    Search for more papers by this author
  • Kurt Polborn

    1. Institut für Organische Chemie der Universität München, Karlstraße 23, D-80333 München, Germany
    Search for more papers by this author

  • Dedicated to Prof. Dr. Christoph Rüchardt on the occasion of his 65th birthday.

Abstract

Perylene-3,4-dicarboximides 2 are obtained by a decarboxylizing condensation of moderately sterically hindered primary amines with perylene-3,4,9,10-tetracarboxylic 3,4:9,10-bisanhydride (3) in the presence of water. Perylene-3,4-dicarboxylic anhydride (4) is prepared by hydrolysis of the imides with KOH in tert-butyl alcohol. The anhydride may be condensed with any primary amine to the corresponding imide. The imides are highly fluorescent and very photostable dyes.

Ancillary