Synthesis and Properties of Novel Highly Fluorescent Pyrrolopyridazine Derivatives

Autor: Michael Bendikov, Teruyuki Mitsumori, Fred Wudl, Josep Sedó
Rok vydání: 2003
Předmět:
Zdroj: Chemistry of Materials. 15:3759-3768
ISSN: 1520-5002
0897-4756
DOI: 10.1021/cm0340532
Popis: 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 calcula...
Databáze: OpenAIRE