Quantum chemical elucidation of the turn-on luminescence mechanism in two new Schiff bases as selective chemosensors of Zn2+: synthesis, theory and bioimaging applications

被引:34
作者
Berrones-Reyes, Jessica C. [1 ]
Munoz-Flores, Blanca M. [1 ]
Canton-Diaz, Arelly M. [1 ]
Treto-Suarez, Manuel A. [2 ]
Paez-Hernandez, Dayan [2 ]
Schott, Eduardo [3 ,5 ]
Zarate, Ximena [4 ]
Jimenez-Perez, Victor M. [1 ]
机构
[1] Univ Autonoma Nuevo Leon, Fac Ciencias Quim, Ciudad Univ, San Nicolas De Los Garza 66451, Nuevo Leon, Mexico
[2] Univ Andres Bello, Ctr Appl Nanosci CENS, Doctorado Fisicoquim Mol, Ave Republ 275, Santiago, Chile
[3] Pontificia Univ Catolica Chile, Fac Quim Farm, UC Energy Res Ctr, Dept Quim Inorgan, Ave Vicuna Mackenna 4860, Santiago, Chile
[4] Univ Autonoma Chile, Fac Ingn, Theoret & Computat Chem Ctr, Inst Ciencias Quim Aplicadas, Ave Pedro de Valdivia 425, Santiago, Chile
[5] Millennium Nuclei Catalyt Proc Sustainable Chem C, Santiago, Chile
关键词
FLUORESCENT-PROBE; PHOTOPHYSICAL PROPERTIES; ELECTRON-TRANSFER; NICKEL-COMPLEXES; NATURAL ORBITALS; ZINC; FLUOROPHORES; TRIVALENT; LIGANDS; VALENCE;
D O I
10.1039/c9ra05010h
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We report the synthesis and characterization of two new selective zinc sensors (S,E)-11-amino-8-((2,4-di-tert-butyl-1-hydroxybenzylidene) amino)-11-oxopentanoic acid (A) and (S,E)-11-amino-8-((8-hydroxybenzylidene)amino)-11-oxopentanoic acid (B) based on a Schiff base and an amino acid. The fluorescent probes, after binding to Zn2+ ions, presented an enhancement in fluorescent emission intensity up to 30 times (phi = A 50.10 and B 18.14%). The estimated LOD for compounds A and B was 1.17 and 1.20 mu M respectively (mixture of acetonitrile : water 1 : 1). Theoretical research has enabled us to rationalize the behaviours of the two selective sensors to Zn2+ synthesized in this work. Our results showed that in the free sensors, PET and ESIPT are responsible for the quenching of the luminescence and that the turn-on of luminescence upon coordination to Zn2+ is mainly induced by the elimination of the PET, which is deeply analysed through EDA, NOCV, molecular structures, excited states and electronic transitions via TD-DFT computations. Confocal fluorescence microscopy experiments demonstrate that compound A could be used as a fluorescent probe for Zn2+ in living cells.
引用
收藏
页码:30778 / 30789
页数:12
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