A selective Fluorescence Chemosensor: Pyrene motif Schiff base derivative for detection of Cu2+ ions in living cells (original) (raw)
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Applied Organometallic Chemistry, 2020
A new "on-off-on" fluorescence chemosensor (DPD) was designed, synthesized, and characterized based on pyrene and benzothiozole hydrazide. The probe DPD shows high affinity towards Cu 2+ ions and the DPD-Cu 2+ ensemble shows high sensitivity towards S 2− ions through the displacement method in the presence of other interfering ions. The detection limits of DPD for Cu 2+ and S 2− ions were found to be 0.73 and 0.87 nM, respectively. Furthermore, the receptor was effectively applied to recognize Cu 2+ and S 2− ions in real samples and live A549 cells through imaging studies.
Dyes and Pigments, 2014
A new, simple and symmetric thiophene based Schiff base 1 as highly selective and fluorescent sensor for Cu 2þ ion detection in aqueous medium over other metal ions has been synthesized. Structure of the receptor 1 was confirmed by single crystal X-ray diffraction and other spectroscopic techniques. Absorption and emission spectra were used to study the cation sensing properties. Receptor 1 displays colorimetric response as yellow to colorless and fluorescence "turn-on" property in presence of Cu 2þ ion. Receptor 1-Cu 2þ complex show 35 folds higher fluorescence response than that of receptor 1. Binding constant for receptor 1-Cu 2þ complex was found as 4.23 Â 10 5 with the detection limit of 0.418 nM. Further the recognition of Cu 2þ ion in the living cell was achieved using fluoresce microscope. Theoretical calculations were done to support the above findings.
Inorganic Chemistry, 2014
A new benzoyl hydrazone based chemosensor R is synthesized by Schiff base condensation of 2,6-diformyl-4methylphenol and phenyl carbohydrazide and acts as a highly selective fluorescence sensor for Cu 2+ and Zn 2+ ions in aqueous media. The reaction of R with CuCl 2 or ZnCl 2 forms the corresponding dimeric dicopper(II) [Cu 2 (R)(CH 3 O)-(NO 3 )] 2 (CH 3 O) 2 (R-Cu 2+ ) and dizinc(II) [Zn 2 (R) 2 ](NO 3 ) 2 (R-Zn 2+ ) complexes, which are characterized, as R, by conventional techniques including single-crystal X-ray analysis. Electronic absorption and fluorescence titration studies of R with different metal cations in a CH 3 CN/0.02 M HEPES buffer medium (pH = 7.3) show a highly selective binding affinity only toward Cu 2+ and Zn 2+ ions even in the presence of other commonly coexisting ions such as Na + , K + , Mg 2+ , Ca 2+ , Mn 2+ , Fe 2+ , Fe 3+ , Co 2+ , Ni 2+ , Cd 2+ , and Hg 2+ . Quantification of the fluorescence titration analysis shows that the chemosensor R can indicate the presence of Cu 2+ and Zn 2+ even at very low concentrations of 17.3 and 16.5 ppb, respectively. R-Zn 2+ acts as a selective metal-based fluorescent sensor for inorganic pyrophosphate ion PPi) even in the presence of other common anions such as F − , Cl − , Br − , I − , CH 3 COO − , CO 3 2− , HCO 3 − , N 3 − , SO 4 2−
A Schiff-based fluorescence sensor for the detection of Cu2+ and its application in living cells
Journal of Photochemistry and Photobiology A: Chemistry, 2019
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Chemically diverse small molecule fluorescent chemosensors for copper ion
The development of sensitive chromogenic chemosensors for sensing Cu 2+ has been receiving much attention in recent years because of their potential application in clinical biochemistry and the environment studies. Numerous chemosensors have been developed for selective recognition of different species on the basis of host–guest interactions such as hydrogen-bonding, electrostatic force, metal–ligand coordination , hydrophobic and van der Waals force of interactions. The simple and rapid sensing of Cu 2+ ions in biological and environmental systems is desirable and the development of selective and sensitive imaging tools capable of monitoring Cu 2+ ions rapidly has attracted considerable attention. Fluorescent chemosensors have served as useful tool for detecting metal ions owing to their intrinsic sensitivity, selectivity and capacity for rapid, real-time monitoring. Small-molecule fluorescent probes can make use of selective, bio-orthogonal chemistries to report on specific analytes in cells and in more complex biological specimens. This review presents a survey of strategies for using small-molecule fluorescent probes to detect Cu 2+ ions which cover UV to NIR regions such as anthracene, pyrene, quinoline, quina-zoline, dansyl, naphthalimide, rhodamine, fluorescein, BODIPY and cyanine dyes.
A new fluorene derived Schiff-base as a dual selective fluorescent probe for Cu2+ and CN−
Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2019
A new fluorene based fluorogenic chemosensor, 2-[(9H-Fluoren-2-ylmethylene)-amino]-phenol (L), has been designed, synthesized, and characterized by CHN analyses and different spectroscopic methods. This turn-on fluorogenic chemosensor shows high selectivity and sensitivity toward Cu 2+ and CN¯ with low detection limits of 1.54 × 10-9 M and 1.83 × 10-7 M, respectively. The stoichiometry ratio of L-Cu 2+ in solution is 1:1, by the method of Job's plot and ESI-MS. The microcrystalline solid product of the chemosensor reaction with copper is characterized as CuL 2. The χT value for CuL 2 is temperature independent at a value of 0.403 cm 3 K mol-1 , which is in agreement with a mononuclear copper(II) complex with an isotropic g-value of 2.075. The fluorescence turn-on recognition process for detection of Cu 2+ is attributed to the restricted imine isomerization and blocking of intramolecular charge transfer (ICT) quenching process in the analyte-bound sensor. The selectivity of L for Cu 2+ is based on the chelationenhanced fluorescence effect (CHEF) mechanism. Other interfering ions such as
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.
Inorganica Chimica Acta, 2017
Schiff base sensors have the advantage of being used through easy, fast, cost-effective and reliable optical methods for sensing toxic metal ions in the environment. In this work, a, simple but highly specific benzildihydrazone based smart probe (1E,2E)-1,2-diphenyl-1,2-bis((E)-(pyridin-2-ylmethylene)hydrazono) ethane (L) has been used for colorimetric detection of Cu 2+ at physiological pH range. Binding interaction between L and various metal ions has been established by UV-Vis spectroscopic measurements, showing favourable coordination towards Cu 2+ and almost no interference with the presence of other metal ions, i.