A pyrene-based simple but highly selective fluorescence sensor for Cu2+ ions via a static excimer mechanism (original) (raw)
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Selective fluorescence detection of Cu2+ in aqueous solution and living cells
Journal of Luminescence, 2014
A rhodamine B semicarbazide 3 was synthesized by the reaction of rhodamine B acid chloride 2 with hydrazine carboxamide hydrochloride under reflux with triethyl amine in acetonitrile. It was used as selective fluorescent and colorimetric sensor for visual detection of Cu 2 þ over competitive ions (Fe 3 þ , Fe 2 þ , Cr 3 þ , Cd 2 þ , Pb 2 þ , Zn 2 þ , Hg 2 þ , Co 2 þ , Ni 2 þ , Ca 2 þ , Mg 2 þ , Ag 2 þ , Mn 2 þ , Sr 2 þ , Cs 2 þ , Na þ , K þ , Li þ ) in aqueous methanol (1:1, v/v), exhibiting a fast response time, less than few second and a detection limit of 1.6 Â 10 À 7 mol/L at neutral pH. The proposed sensing system can be successfully applicable for determination of Cu 2 þ in waste water samples showing turn on fluorescence response and for further monitoring of intracellular Cu 2 þ levels in living cells with high sensitivity and selectivity at micro molar level concentrations using confocal fluorescence spectroscopy. The synthesis of probe 3 was confirmed by 1 H NMR, 13 C NMR and mass spectrometric analysis.
ACS Omega
Herein, we report the synthesis and characterization of a chemosensor, 5-(diethylamino)-2-(2,3-dihydro-1H-perimidin-2-yl)phenol (HL), synthesized from a condensation between 4-(diethylamino)salicylaldehyde and 1,8-diaminonaphthalene. Upon investigation of the sensing properties of HL, it was found that this sensor may be employed for simple yet efficient detection of Cu 2+ in aqueous methanol solutions. The selective and ratiometric response to Cu 2+ yielded an outstandingly low limit of detection of 3.7 nM by spectrophotometry and is also useful as a naked-eye sensor from 2.5 μM. The system was studied by spectrophotometric pH titrations to determine Cu 2+ binding constants and complex speciation. Binding of Cu 2+ to HL occurs in 1:1 stoichiometry, in good agreement with high-resolution electrospray ionization mass spectrometry (ESI-HRMS) results, Cu 2+ titrations, and Job's plot experiments, while the coordination geometry was tentatively assigned as square pyramidal by spectroscopic studies.
Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2019
A fluorescein-based nano probe was designed and synthesized for ultra-sensitive detection of Cu 2+ in aqueous solution. The formation of fluorescent organic nanoparticles confirmed by using particle size analysis and scanning electron microscopy. UV-Vis. absorption and fluorescence spectroscopy displays excellent photophysical properties of prepared nanoparticles as compared to parent molecule i.e. N-(3′,6′-dihydroxy-3-oxo-3,3adihydrospiro[isoindole-1,9′-xanthene]-2(7aH)-yl)-1-naphthamide (FNH) in acetone. A series of 18 metal ion was examined with FNH nanoparticles (FNHNPs) to examine the change in fluorescence response. Pleasingly, only copper ion (Cu 2+) shows selective and sensitive fluorescence enhancement effect, which discussed on chelation-enhanced fluorescence phenomenon. Other competing metal ions does not affect the FNHNPs fluorescence enhancement induced by Cu 2+ ion. The excited state complexation through chelation-enhanced fluorescence of FNHNPs was further supported by UV-Vis. absorption and fluorescence decay titration of FNHNPs with and without the addition of Cu 2+. The present investigation approach serves extremely low detection limit of 1.62 ng/mL (0.024 μM) for Cu 2+ in aqueous solution. In addition, benefit of present study includes practical application for the quantitative estimation of Cu 2+ in drinking water sample and intracellular cell imaging for Cu 2+ .
“ ON – OFF ” probe for colorimetric and fl uorometric sensing of Cu 2 + in water †
2017
Department of Chemistry, University of Ca India. E-mail: sgchem@caluniv.ac.in; goswa Departament de Qúımica, Universitat de les 07122 Palma de Mallorca, Baleares, Spain Department of Microbiology, University of Kolkata, India † Electronic supplementary information (E of H5dpm, photophysical characterization CCDC 1529126. For ESI and crystallogr format see DOI: 10.1039/c6ra27017d Cite this: RSC Adv., 2017, 7, 11312
Tetrahedron Letters, 2010
Schiff base sensor 1, containing naphthalene and naphthalimide fluorophores with separate and distinct emission wavelengths, showed good selectivity for Cu(II) over other tested physiological and environmentally important cations through changes in its fluorescence spectra in THF/H 2 O (9:1) HEPES buffered solution. By taking the ratiometric change of the emissions at 435 nm (naphthalene-Schiff base) and 510 nm (naphthalimide) good linearity was observed in the 0-10 lM range. The enhancement of the 435 nm emission upon binding Cu 2+ was attributed to a prevention of the rapid C@N isomerisation that otherwise leads to non-radiative decay, while the quenching of the naphthalimide emission was attributed to electron transfer between the excited naphthalimide fluorophore and the redox active Cu 2+ .
Fluorescence Chemosensory Determination of Cu2+ Using a New Rhodamine–Morpholine Conjugate
Chemosensors
A new rhodamine-B carbonyl-morpholine derivative (denoted as RECM) was prepared by a two-step synthesis procedure. The employed method allowed a lactam ring development of rhodamine-B and ethylenediamine to demonstrate a facile amide bond formation. The obtained RECM was confirmed by 1 H NMR, 13 C NMR, and mass spectrometry analysis. RECM was formed to detect copper ion (Cu 2+) due to its problematic toxicity features in aquatic ecosystems. It showed a high selectivity toward Cu 2+ in comparison with some environmentally relevant alkali, alkaline earth, and transition metal cations at 50 µM in acetonitrile. Moreover, non-fluorescent RECM showed fluorescence intensity and UV-Vis absorbance increases in the presence of Cu 2+ with high linear dependent coefficients (R 2 = 0.964 and R 2 = 0.982 respectively) as well as a color change from colorless to pink owing to the ring opening of the rhodamine spirolactam form. Binding capability experiments presented a clear 1:1 stoichiometry of RECM-Cu 2+ complex with the binding constant (K a) as 2.25 × 10 4 M −1. The calculation of limits of detection (LOD) was 0.21 µM based on the linear regression method, which is below the maximum contaminant level goal (MCLG) value of Cu 2+ (1.3 ppm equals to 20.46 µM) in drinking water. These characteristics make the RECM a promising candidate for the real-time detection of toxic Cu 2+ in environmental monitoring applications.
Materials advances, 2022
In this work, we developed a simple fluorescent colorimetric chemosensor H 2 L [6,6 0-((1,1 0)-hydrazine-1,2-diylidene bis(methanylylidene)) bis(2-(6-methoxy)) phenol] for rapid detection of Cu 2+ in aqueous solution. The method for synthesis of H 2 L is very simple and environment friendly. This organic Schiff base probe was characterized by 1 H-NMR, FT-IR and ESI-MS spectroscopy along with single-crystal XRD analysis. It exhibited binding-induced colour change with Cu 2+ ion from colourless to intense yellow and fluorescence enhancement. The LOD values of H 2 L towards Cu 2+ were calculated to be 7.1 Â 10 À8 M (colorimetrically) and 3.8 Â 10 À8 M (fluorometrically). The interactions between H 2 L and Cu 2+ were studied by Job's plot, ESI-MS, FT-IR spectroscopy and DFT calculations. The crystal structure of the L-Cu 2+ adduct was also determined by single-crystal X-ray analysis, and it was found that two molecules of L coordinate with three molecules of Cu 2+ ions. The receptor H 2 L could operate in a wide pH range and can be successfully applied for detection and quantification of Cu 2+ ions in environmental samples and logic applications.
Colorimetric detection of cyanide in water using a highly selective Cu 2+ chemosensor
Inorganic Chemistry Communications, 2009
In this manuscript, we report that easily available N,N-dimethyldipyrromethane (1) demonstrates a high chromogenic selectivity for Cu 2+ over other cations with detection limit 4.76 ppm. The complex of Cu 2+ with 1 displayed ability to detect up to 6.5 ppm CN À from water. Both the processes proceed with distinct visual color changes.