Synthesis and Photophysical Properties of Fluorescent 6-Aryl-D-π-A Coumarin Derivatives

Andrea Cocco
Primo
Membro del Collaboration Group
;
Paola Caria
Membro del Collaboration Group
;
Giuseppina Sanna
Membro del Collaboration Group
;
Enzo Cadoni
Membro del Collaboration Group
;
Riccardo Corpino
Membro del Collaboration Group
;
Pier Carlo Ricci
Membro del Collaboration Group
;
Carlo Maria Carbonaro
Penultimo
;
Francesco Secci
Ultimo
Membro del Collaboration Group
2021

Abstract

A series of 6-aryl coumarin dyes were synthesized in satisfactory yields by Pd-catalyzed Suzuki cross-coupling reactions with a panel of boronic acids and coumarin bromides. Photophysical studies highlighted a large Stoke shift and interesting fluorescence quantum yield for these compounds. Optical properties were also investigated with the aid of quantum chemical calculations. The treatment of selected coumarin dyes with increasing amounts of trifluoroacetic acid showed that their fluorescence can be strongly influenced by pH (fluorescence quenching at high acid concentrations), while the addition of Fe3+ and Al3+ metal ions allowed to highlight dichotomous behavior with the corresponding reduction in fluorescence with the increase of [Fe3+] or [Al3+]. Finally, biological assays and fluorescence microscopy imaging investigations indicated that these compounds can be used as potential biomarkers in living and fixed cells.
Inglese
6
49
33708
33716
9
Esperti anonimi
internazionale
scientifica
Coumarins; Donor-acceptor; Bioimaging
no
Cocco, Andrea; Caria, Paola; Sanna, Giuseppina; Stagi, Luigi; Cadoni, Enzo; Corpino, Riccardo; Ricci, PIER CARLO; Carbonaro, CARLO MARIA; Secci, Francesco
1.1 Articolo in rivista
info:eu-repo/semantics/article
1 Contributo su Rivista::1.1 Articolo in rivista
262
9
open
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