Highly Fluorescent, pi-Extended Indenopyrido[2,1-a]isoindolone Derivatives Prepared by a Palladium-Catalysed Cascade Reaction

Autor: Chamas, Zein el Abidine, Marchi, Enrico, Modelli, Alberto, Fort, Yves, Ceroni, Paola, Mamane, Victor
Přispěvatelé: Structure et Réactivité des Systèmes Moléculaires Complexes (SRSMC), Institut de Chimie du CNRS (INC)-Université de Lorraine (UL)-Centre National de la Recherche Scientifique (CNRS), Alma Mater Studiorum Università di Bologna [Bologna] (UNIBO)
Jazyk: angličtina
Rok vydání: 2013
Předmět:
Zdroj: European Journal of Organic Chemistry
European Journal of Organic Chemistry, Wiley-VCH Verlag, 2013, pp.2316-2324. ⟨10.1002/ejoc.201201575⟩
ISSN: 1434-193X
1099-0690
DOI: 10.1002/ejoc.201201575⟩
Popis: International audience; A new family of heterocyclic pentacyclic compounds have been prepared by a cascade reaction involving 2,5-dihalopyridines and (2-formylphenyl)boronic acids. Most of the compounds exhibit high quantum yields of fluorescence in dichloromethane. In some cases, small changes in the substitution pattern caused fluorescence quenching. To rationalize this effect, a detailed photophysical study combined with electrochemical and computational studies was performed on four representative derivatives. It appears that the fluorescence quenching is caused by a thermally activated non-radiative deactivation process that can be prevented in a rigid matrix such as ethanol at 77 K or a PMMA polymer.
Databáze: OpenAIRE
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