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.

Highly fluorescent p-extended indenopyrido[2,1-a]isoindolone derivatives prepared by a palladium-catalyzed cascde reaction / Z. Chamas; E. Marchi; A. Modelli; Y. Fort; P. Ceroni; V. Mamane. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - STAMPA. - 2013:(2013), pp. 2316-2324. [10.1002/ejoc.201201575]

Highly fluorescent p-extended indenopyrido[2,1-a]isoindolone derivatives prepared by a palladium-catalyzed cascde reaction

MARCHI, ENRICO;MODELLI, ALBERTO;CERONI, PAOLA;
2013

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.
2013
Highly fluorescent p-extended indenopyrido[2,1-a]isoindolone derivatives prepared by a palladium-catalyzed cascde reaction / Z. Chamas; E. Marchi; A. Modelli; Y. Fort; P. Ceroni; V. Mamane. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - STAMPA. - 2013:(2013), pp. 2316-2324. [10.1002/ejoc.201201575]
Z. Chamas; E. Marchi; A. Modelli; Y. Fort; P. Ceroni; V. Mamane
File in questo prodotto:
Eventuali allegati, non sono esposti

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11585/136194
 Attenzione

Attenzione! I dati visualizzati non sono stati sottoposti a validazione da parte dell'ateneo

Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 15
  • ???jsp.display-item.citation.isi??? 15
social impact