Quantum chemical elucidation of the turn-on luminescence mechanism in two new Schiff bases as selective chemosensors of Zn 2+ : synthesis, theory and bioimaging applications.

Autor:	Berrones-Reyes JC; Universidad Autónoma de Nuevo León, Facultad de Ciencias Químicas, Ciudad Universitaria 66451 Nuevo León México victor.jimenezpr@uanl.edu.mx., Muñoz-Flores BM; Universidad Autónoma de Nuevo León, Facultad de Ciencias Químicas, Ciudad Universitaria 66451 Nuevo León México victor.jimenezpr@uanl.edu.mx., Cantón-Diáz AM; Universidad Autónoma de Nuevo León, Facultad de Ciencias Químicas, Ciudad Universitaria 66451 Nuevo León México victor.jimenezpr@uanl.edu.mx., Treto-Suárez MA; Doctorado en Fisicoquímica Molecular, Center of Applied Nanosciences (CENS), Universidad Andres Bello Ave. República #275 Santiago de Chile Chile., Páez-Hernández D; Doctorado en Fisicoquímica Molecular, Center of Applied Nanosciences (CENS), Universidad Andres Bello Ave. República #275 Santiago de Chile Chile., Schott E; Departamento de Química Inorgánica, UC Energy Research Center, Facultad de Química de Farmacia, Pontificia Universidad Católica de Chile Avenida Vicuña Mackenna, 4860 Macul Santiago Chile.; Millennium Nuclei on Catalytic Processes towards Sustainable Chemistry (CSC) Chile., Zarate X; Instituto de Ciencias Químicas Aplicadas, Theoretical and Computational Chemistry Center, Facultad de Ingeniería, Universidad Autónoma de Chile Av. Pedro de Valdivia 425 Santiago Chile jazminac@gmail.com., Jiménez-Pérez VM; Universidad Autónoma de Nuevo León, Facultad de Ciencias Químicas, Ciudad Universitaria 66451 Nuevo León México victor.jimenezpr@uanl.edu.mx.
Jazyk:	angličtina
Zdroj:	RSC advances [RSC Adv] 2019 Sep 30; Vol. 9 (53), pp. 30778-30789. Date of Electronic Publication: 2019 Sep 30 (Print Publication: 2019).
DOI:	10.1039/c9ra05010h
Abstrakt:	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 Zn 2+ ions, presented an enhancement in fluorescent emission intensity up to 30 times ( ϕ = A 50.10 and B 18.14%). The estimated LOD for compounds A and B was 1.17 and 1.20 μM respectively (mixture of acetonitrile : water 1 : 1). Theoretical research has enabled us to rationalize the behaviours of the two selective sensors to Zn 2+ 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 Zn 2+ 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 Zn 2+ in living cells. Competing Interests: There are no conflicts of interest. (This journal is © The Royal Society of Chemistry.)
Databáze:	MEDLINE
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