European Journal of Organic Chemistry p. 2316 - 2324 (2013)
Update date:2022-08-04
Topics: Derivatives Cascade reaction Fluorescent Palladium-catalysed
El Abidine Chamas, Zein
Marchi, Enrico
Modelli, Alberto
Fort, Yves
Ceroni, Paola
Mamane, Victor
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.
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