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

Jessica C. Berrones-Reyes, Blanca M. Muñoz-Flores, Arelly M. Cantón-Diáz, Manuel A. Treto-Suárez, Dayan Páez-Hernández, Eduardo Schott, Ximena Zarate, Víctor M. Jiménez-Pérez

Research output: Contribution to journalArticlepeer-review

9 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)30778-30789
Number of pages12
JournalRSC Advances
Volume9
Issue number53
DOIs
Publication statusPublished - 1 Jan 2019

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)

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