Unprecedented rearrangement of diketopyrrolopyrroles leads to structurally unique chromophores
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Updated: Feb 20, 2026

Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
Published on: June 10, 2021
Olena Vakuliuk1, Shota Ooi1, Irena Deperasińska2
1Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland. dtgryko@icho.edu.pl.
Abstract:
Diketopyrrolopyrroles possessing thienyl, furyl and benzofuryl substituents undergo unprecedented skeletal rearrangement in the presence of trimethylsilyl bromide resulting in the formation of thieno[2,3-f]isoindole-5,8-diones and furo[2,3-f]isoindole-5,8-diones. These relatively small dyes possess favorable photophysical properties with the emission maxima within the range of 573-624 nm, large fluorescence quantum yields, moderate sensitivity of emission to solvent polarity and a HOMO-LUMO gap of ca. 1.8 eV.
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