Chalcone-based fluorescent chemosensors as new tools for detecting Cu2+ ions

Gomes, Liliana J; Moreira, Teresa; Rodrı̀guez, Laura; Moro, Artur J.

doi:10.1016/j.dyepig.2021.109845

Cited by 11 publications

(9 citation statements)

References 28 publications

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“…Chemosensor 1 was designed to possess the flavylium chromophoric unit coupled to a DPA metal chelating moiety. The synthesis was performed by condensation of (E)-2-(4-((2-(bis(pyridin-2-ylmethyl)amino)ethyl)(methyl)amino)benzylidene)cyclohexanone ( A ) [ 41 ] with 4-(diethylamino)salicylaldehyde ( B ) allowed to obtain styrylflavylium 1 ( Figure 2 ).…”

Section: Resultsmentioning

confidence: 99%

A Near InfraRed Emissive Chemosensor for Zn2+ and Phosphate Derivatives Based on a Di-(2-picolyl)amine-styrylflavylium Push-Pull Fluorophore

Gomes

Carrilho

Pereira

et al. 2023

Sensors

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A new Near InfraRed (NIR) fluorescent chemosensor for metal ions and anions is herein presented. The fluorophore is based on a styrylflavylium dye, a synthetic analogue of the natural anthocyanin family, with a di-(2-picolyl)amine (DPA) moiety as the metal chelating unit. The substitution pattern of the styrylflavylium core (with tertiary amines on positions 7 and 4′) shifts the optical properties of the dye towards the NIR region of the electronic spectra, due to a strong push-pull character over the π-conjugated system. The NIR chemosensor is highly sensitive to the presence of Zn2+, which induces a strong CHelation Enhanced Fluorescence (CHEF) effect upon binding to the DPA unit (2.7 fold increase). The strongest competing ion is Cu2+, with a complete fluorescence quenching, while other metals induce lower responses on the optical properties of the chemosensor. Subsequent anion screening of the Zn2+-chemosensor coordination compound has demonstrated a distinct selectivity towards adenosine 5′-triphosphate (ATP) and adenosine 5′-diphosphate (ADP), with high association constants (K ~ 106 M−1) and a strong CHEF effect (2.4 and 2.9 fold fluorescence increase for ATP and ADP, respectively). Intracellular studies with the Zn2+-complexed sensor showed strong luminescence in the cellular membrane of Gram– bacteria (E. coli) and mitochondrial membrane of mammalian cells (A659), which highlights its possible application for intracellular labelling.

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Section: Resultsmentioning

confidence: 99%

A Near InfraRed Emissive Chemosensor for Zn2+ and Phosphate Derivatives Based on a Di-(2-picolyl)amine-styrylflavylium Push-Pull Fluorophore

Gomes

Carrilho

Pereira

et al. 2023

Sensors

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“…DPA-based sensors for Cu 2+ with several different fluorophores have been reported, including ruthenium (II) [7,8] and iridium (II) [9] complexes, naphthalimide [10][11][12], chalcones [13] and BODIPY dyes [14,15], among others [16].…”

Section: Introductionmentioning

confidence: 99%

An NIR Emissive Donor-π-Acceptor Dicyanomethylene-4H-Pyran Derivative as a Fluorescent Chemosensor System towards Copper (II) Detection

Karkosik

Moro

2022

Chemosensors

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A novel donor-π-acceptor fluorescent dye as a chemosensor for Cu2+ ions is herein presented. The fluorophoric core consists of a 3,5-diphenyl-dicyanomethylene-4H-pyran (DCM), with extended styryl chains on positions 2 and 6, bearing terminal di-(2-picolyl)amine (DPA) groups for metal coordination. Optical characterization of the chemosensor dye reveals an absorption maximum at ca. 500 nm and a strong bathochromic shift in the emission, reaching ca. 750 nm in polar solvents. This solvatochromic behavior, which yields very large Stokes shifts (up to ~6700 cm−1), is characteristic of the strong intramolecular Charge Transfer (CT) nature of this chromophoric system. While the chemosensor has demonstrated no changes in its optical properties over a wide pH range (2–12), a strong quenching effect was observed upon Cu2+ coordination, with a 1:1 binding stoichiometry, indicating that only one DPA unit is capable of effectively chelating Cu2+, rendering the second DPA motif inactive. The binding constant was determined to be 7.5 × 107 M−1, indicating a very high sensitivity, and an LOD of 90.1 nM. Competition assays have demonstrated that the chemosensor is highly selective towards Cu2+, even in the presence of excesses of other mono- and di-valent cations. Co2+ and Ni2+ proved to be the strongest interferents, particularly in the luminescent response. Paper test-strips prepared with the embedded sensor showed a fluorometric response in the presence of different copper (II) concentrations, which attested to the potential of this chemosensor to be used in the determination of Cu2+ content in aqueous media, for in-field applications.

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“…Relevant distances in Å: 1L 1 : Pd-Cl = 2.2903(7), Pd-P = 2.3231(7), CvC (olefin) = 1.314(4). 4L 1 : Pd-C = 1.990(4), Pd-P = 2.3388(10), CvC (olefin) = 1.320(6). 5L 1 : Pt-Cl = 2.3029(11), Pt-P = 2.3241(11), CvC (olefin) = 1.303(7).…”

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confidence: 99%

“…5 Moreover, chemosensors with chalcone-based chromophores have been applied for the selective detection of Cu 2+ in aqueous media. 6 Besides, there is a report on the application of chalcone-derived liquid crystals for NH 3 (g) sensing. 7 Our pursuit of hemilabile ligands able to promote challenging Pd-catalysed C-C couplings (e.g.…”

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confidence: 99%

“…In the free phosphine ligands, the chalcone moiety is clearly affected by the orbital influence of the R substituents at the P atom, as supported by the variations in their λ emis values (Table 1, entries 1-3). In the complexes, additional dependence on the MX 2 metal fragment at which phosphine is coordinated is obvious (Table 1, entries [4][5][6][7][8][9][10][11].…”

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Solid state luminescence of phosphine-EWO ligands with fluorinated chalcone skeletons and their PdX₂ complexes: metal-promoted phosphorescence enhancement

et al. 2023

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Chalcone-based fluorescent chemosensors as new tools for detecting Cu2+ ions

Cited by 11 publications

References 28 publications

A Near InfraRed Emissive Chemosensor for Zn2+ and Phosphate Derivatives Based on a Di-(2-picolyl)amine-styrylflavylium Push-Pull Fluorophore

A Near InfraRed Emissive Chemosensor for Zn2+ and Phosphate Derivatives Based on a Di-(2-picolyl)amine-styrylflavylium Push-Pull Fluorophore

An NIR Emissive Donor-π-Acceptor Dicyanomethylene-4H-Pyran Derivative as a Fluorescent Chemosensor System towards Copper (II) Detection

Solid state luminescence of phosphine-EWO ligands with fluorinated chalcone skeletons and their PdX₂ complexes: metal-promoted phosphorescence enhancement

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Chalcone-based fluorescent chemosensors as new tools for detecting Cu2+ ions

Cited by 11 publications

References 28 publications

A Near InfraRed Emissive Chemosensor for Zn2+ and Phosphate Derivatives Based on a Di-(2-picolyl)amine-styrylflavylium Push-Pull Fluorophore

A Near InfraRed Emissive Chemosensor for Zn2+ and Phosphate Derivatives Based on a Di-(2-picolyl)amine-styrylflavylium Push-Pull Fluorophore

An NIR Emissive Donor-π-Acceptor Dicyanomethylene-4H-Pyran Derivative as a Fluorescent Chemosensor System towards Copper (II) Detection

Solid state luminescence of phosphine-EWO ligands with fluorinated chalcone skeletons and their PdX2 complexes: metal-promoted phosphorescence enhancement

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Solid state luminescence of phosphine-EWO ligands with fluorinated chalcone skeletons and their PdX₂ complexes: metal-promoted phosphorescence enhancement