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Issue 53, 2019
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Quantum chemical elucidation of the turn-on luminescence mechanism in two new Schiff bases as selective chemosensors of Zn2+: synthesis, theory and bioimaging applications

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Abstract

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 (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 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.

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

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Article information


Submitted
02 Jul 2019
Accepted
21 Aug 2019
First published
30 Sep 2019

This article is Open Access

RSC Adv., 2019,9, 30778-30789
Article type
Paper

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

J. C. Berrones-Reyes, B. M. Muñoz-Flores, A. M. Cantón-Diáz, M. A. Treto-Suárez, D. Páez-Hernández, E. Schott, X. Zarate and V. M. Jiménez-Pérez, RSC Adv., 2019, 9, 30778
DOI: 10.1039/C9RA05010H

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