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

Abstract : 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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https://hal.univ-lorraine.fr/hal-01493936
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Submitted on : Wednesday, March 22, 2017 - 1:53:12 PM
Last modification on : Friday, February 26, 2021 - 3:24:02 PM

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Zein El Abidine Chamas, Enrico Marchi, Alberto Modelli, Yves Fort, Paola Ceroni, et al.. Highly Fluorescent, pi-Extended Indenopyrido[2,1-a]isoindolone Derivatives Prepared by a Palladium-Catalysed Cascade Reaction. European Journal of Organic Chemistry, Wiley-VCH Verlag, 2013, pp.2316-2324. ⟨10.1002/ejoc.201201575⟩. ⟨hal-01493936⟩

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