Synthesis and properties of novel highly fluorescent pyrrolopyridazine derivatives

Teruyuki Mitsumori, Michael Bendikov, Josep Sedó, Fred Wudl

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72 Citations (Scopus)

Abstract

We report here the synthesis, X-ray structures, optical and electrochemical properties, and density functional calculations for new pyrrolopyridazine derivatives. Ten strongly luminescent heterocycles were synthesized by 1,3-dipolar cycloaddition reactions between alkylated pyridazine or cinnoline and naphthoquinone or dimethyl acetylenedicarboxylate (DMAD). They are benzo[f]pyridazino[6,1-a]isoindole-5,10-diones (BPID) 1-4, benzo[f]-pyridazino[6,1-a]isoindole (BPI) 5, pyrrolo[1,2-b]cinnolines (PC) 6 and 7, and pyrrolo[1,2-b]pyridazines (PP) 8-10. The relative luminescence quantum yield can be as high as 90% and the heterocycles are luminescent in the solid state, which indicates that there is little self-quenching in these systems. Furthermore, we have shown that the optical properties of pyrrolopyridazines can be tuned by substitutions in different ring positions. An unexpected blue shift and a large red shift with a different π conjugation system were explained by aromaticity arguments using DFT calculations and X-ray crystal structures. Electrochemical investigation has shown that the redo potentials of the new heterocycles could be controlled by design. The synthesis of a series of compounds allowed detailed analysis of substituent effects on structures, frontier orbitals, and luminescent and electrochemical properties.

Original languageEnglish
Pages (from-to)3759-3768
Number of pages10
JournalChemistry of Materials
Volume15
Issue number20
DOIs
Publication statusPublished - Oct 7 2003

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ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)
  • Materials Chemistry

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