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Updated: May 1, 2026

Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
Published on: June 10, 2021
Azacyanines of the pyrrolopyrrole series
Timo Marks1, Ewald Daltrozzo, Andreas Zumbusch
1Fachbereich Chemie, Universität Konstanz, 78457 Konstanz (Germany), Fax: (+49) 7531-88-3139.
Abstract:
The reaction of POCl3-activated, readily soluble diketopyrrolopyrrole (DPP) with 2-aminoheteroaromatics to yield 1:1 and 1:2 hydrogen chelates is described. Complexation of these hydrogen chelates with boron reagents results in thermally and photochemically stable fluorescent dyes (PP-azacyanines). The 1:2 complexes in particular absorb at long wavelengths and are brightly fluorescing. The rich photophysics of the new compounds are presented. Both the pronounced vibrational fine structure of the S0 → S1 transitions and the observed fluorescence phenomena allow detailed conclusions to be made on the correlation between molecular structure and optical properties.
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