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

被引:12
|
作者
Cocco, Andrea [1 ]
Caria, Paola [2 ]
Sanna, Giuseppina [2 ]
Stagi, Luigi [3 ]
Cadoni, Enzo [1 ]
Corpino, Riccardo [4 ]
Ricci, Pier Carlo [4 ]
Carbonaro, Carlo Maria [4 ]
Secci, Francesco [1 ]
机构
[1] Univ Cagliari, Dept Chem & Geol Sci, I-09042 Cagliari, Italy
[2] Univ Cagliari, Dept Biomed Sci, I-09042 Cagliari, Italy
[3] Univ Sassari, Dept Chem & Pharm, Lab Mat Sci & Nanotechnol, CR INSTM, I-07100 Sassari, Italy
[4] Univ Cagliari, Dept Phys, I-09042 Cagliari, Italy
来源
ACS OMEGA | 2021年 / 6卷 / 49期
关键词
QUANTUM YIELDS; CELL; TRIPHENYLAMINE; MOLECULE; DYES;
D O I
10.1021/acsomega.1c04810
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
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 AN. Finally, biological assays and fluorescence microscopy imaging investigations indicated that these compounds can be used as potential biomarkers in living and fixed cells.
引用
收藏
页码:33708 / 33716
页数:9
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