Isoquinolinylpyrazoles and pyridylisoxazoles as luminescent materials with sensorial ability towards pollutant toxic metal ions. Experimental and computational studies

Cristián Cuerva, Nuno Morais, José A. Campo, Mercedes Cano, Carlos Lodeiro

Research output: Contribution to journalArticle

Abstract

The crystal structure and photoluminescence behaviour of two series of azole-based derivatives have been investigated. In the solid state, the compounds form head-to-tail dimers through intermolecular hydrogen bonds and emit bluish light in the range of 340–500 nm. The geometry parameters have been optimised by DFT calculations to analyse the molecular electrostatic potential (MEP) and the charge distribution in order to find the favourable molecular sites for metal interactions. The electronic properties of the frontier orbitals and their energy levels have been also measured. The compounds behave as fluorescent materials in solution and they exhibit sensorial abilities towards Hg2+, Pd2+, Pt4+, Cu2+, Zn2+ and Cd2+ metal ions. The ion sensing properties that the azoles present upon complexation have been followed by spectrophotometric and spectrofluorimetric titrations. Additionally, the stability constants of the complexes formed as well as the detection and quantification limits have been calculated. The best results are obtained for the detection of Zn2+ at concentration lower than 0.3 µM.

Original languageEnglish
Pages (from-to)517-530
Number of pages14
JournalJournal of Luminescence
Volume198
DOIs
Publication statusPublished - 1 Jun 2018

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Azoles
Poisons
azoles
contaminants
Metal ions
metal ions
Metals
Ions
Charge distribution
Complexation
Static Electricity
Titration
Discrete Fourier transforms
Electronic properties
Dimers
Electron energy levels
Limit of Detection
Hydrogen
Electrostatics
Photoluminescence

Keywords

  • Azoles
  • Chelation
  • Ion sensing
  • Luminescence
  • Toxic ions

Cite this

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title = "Isoquinolinylpyrazoles and pyridylisoxazoles as luminescent materials with sensorial ability towards pollutant toxic metal ions. Experimental and computational studies",
abstract = "The crystal structure and photoluminescence behaviour of two series of azole-based derivatives have been investigated. In the solid state, the compounds form head-to-tail dimers through intermolecular hydrogen bonds and emit bluish light in the range of 340–500 nm. The geometry parameters have been optimised by DFT calculations to analyse the molecular electrostatic potential (MEP) and the charge distribution in order to find the favourable molecular sites for metal interactions. The electronic properties of the frontier orbitals and their energy levels have been also measured. The compounds behave as fluorescent materials in solution and they exhibit sensorial abilities towards Hg2+, Pd2+, Pt4+, Cu2+, Zn2+ and Cd2+ metal ions. The ion sensing properties that the azoles present upon complexation have been followed by spectrophotometric and spectrofluorimetric titrations. Additionally, the stability constants of the complexes formed as well as the detection and quantification limits have been calculated. The best results are obtained for the detection of Zn2+ at concentration lower than 0.3 µM.",
keywords = "Azoles, Chelation, Ion sensing, Luminescence, Toxic ions",
author = "Cristi{\'a}n Cuerva and Nuno Morais and Campo, {Jos{\'e} A.} and Mercedes Cano and Carlos Lodeiro",
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year = "2018",
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T1 - Isoquinolinylpyrazoles and pyridylisoxazoles as luminescent materials with sensorial ability towards pollutant toxic metal ions. Experimental and computational studies

AU - Cuerva, Cristián

AU - Morais, Nuno

AU - Campo, José A.

AU - Cano, Mercedes

AU - Lodeiro, Carlos

N1 - info:eu-repo/grantAgreement/FCT/5876/147258/PT# Project CTQ2015-63858-P (MINECO/FEDER). Sem PDF conforme despacho.

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N2 - The crystal structure and photoluminescence behaviour of two series of azole-based derivatives have been investigated. In the solid state, the compounds form head-to-tail dimers through intermolecular hydrogen bonds and emit bluish light in the range of 340–500 nm. The geometry parameters have been optimised by DFT calculations to analyse the molecular electrostatic potential (MEP) and the charge distribution in order to find the favourable molecular sites for metal interactions. The electronic properties of the frontier orbitals and their energy levels have been also measured. The compounds behave as fluorescent materials in solution and they exhibit sensorial abilities towards Hg2+, Pd2+, Pt4+, Cu2+, Zn2+ and Cd2+ metal ions. The ion sensing properties that the azoles present upon complexation have been followed by spectrophotometric and spectrofluorimetric titrations. Additionally, the stability constants of the complexes formed as well as the detection and quantification limits have been calculated. The best results are obtained for the detection of Zn2+ at concentration lower than 0.3 µM.

AB - The crystal structure and photoluminescence behaviour of two series of azole-based derivatives have been investigated. In the solid state, the compounds form head-to-tail dimers through intermolecular hydrogen bonds and emit bluish light in the range of 340–500 nm. The geometry parameters have been optimised by DFT calculations to analyse the molecular electrostatic potential (MEP) and the charge distribution in order to find the favourable molecular sites for metal interactions. The electronic properties of the frontier orbitals and their energy levels have been also measured. The compounds behave as fluorescent materials in solution and they exhibit sensorial abilities towards Hg2+, Pd2+, Pt4+, Cu2+, Zn2+ and Cd2+ metal ions. The ion sensing properties that the azoles present upon complexation have been followed by spectrophotometric and spectrofluorimetric titrations. Additionally, the stability constants of the complexes formed as well as the detection and quantification limits have been calculated. The best results are obtained for the detection of Zn2+ at concentration lower than 0.3 µM.

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KW - Ion sensing

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KW - Toxic ions

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