One-Step Cascade Synthesis of --Imidazolo-Extended Perylene Biscarboximides (OBISIM) and Their Application as Broad-Spectrum Fluorescent Dyes.

A one-step synthesis of perylene dyes with lateral extension by condensed imidazoles in a cascade reaction of sodium amide and benzonitrile is described in which multiple extensions can be controlled by the reaction conditions. The extensions lead to bathochromic shifts in absorption and fluorescence while maintaining high fluorescence quantum yields. The condensed imidazole units cause additional absorption bands in the hypsochromic visible region, resulting in broad-band absorbers.

Thermochromism of perylenes: dynamics in aromatics.

A thermal equilibrium between planar and skew perylene derivatives induces thermochromism and may modulate molecular recognition. Thus, the long-lasting discussion about the geometry of perylene could be solved in terms of this equilibrium. Extension to other aromatics and practical applications such as for non contact fluorescence thermometers are discussed.

Laterally extended naphthalene tetracarboxylic bisimides.

The colorless naphthalene tetracarboxylic bisimides were laterally extended with imidazole rings to give colored and highly fluorescent materials. Donor-substituted phenyl groups at the imidazole rings cause further bathochromic shifts in fluorescence where the strong solvent influence in the spectra is typical for a TICT process. Applications are discussed.