Pyrene based Schiff base ligand: A highly selective fluorescence chemosensor for the detection of Cu2+ ions

A Schiff base ligand L has been designed and synthesized by the condensation of 1′-Hydroxy-2′-acetonaphthonehydrazide with pyrene aldehyde for the detection of Cu²⁺ ions. The ligand was spectroscopically characterized by all possible techniques. Among different metal ions, Cu²⁺ ions give a tremendous enhancement of fluorescence intensity in 20% water with THF. The “Turn-On” fluorescence for Cu²⁺ ions utilizes the Photo-induced Electron Transfer (PET) mechanism. It has been observed that the presence of relevant cations and anions did not affect the probe's fluorescence intensity. The stoichiometric binding mode of the complex is confirmed using Job's method. The low detection limit and reversibility make it cost-effective.     

A highly selective and sensitive fluorescent turn-on chemosensor for Al3+ based on a chromone Schiff base

A Schiff-base fluorescent sensor, 7-methoxychromone-3-carbaldehyde-(3′,4′-dimethyl)pyrrole hydrazone (MCPH), was synthesized. The new sensor showed high selectivity for Al³⁺ over other metal ions examined in acetonitrile. Upon binding Al³⁺, a significant fluorescence enhancement with a turn-on ratio over 101-fold was triggered. The detection limit of MCPH for Al³⁺ was 2.5?×?10^?7?mol?L^?1.     

A highly selective and sensitive dual-channel chemosensor for cyanide based on sulfahydrazone derivative

A colorimetric and fluorescent cyanide probe bearing naphthol and sulfahydrazone groups has been designed and synthesized. This structurally simple probe displays a rapid response and high selectivity for cyanide in DMSO/EtOH (v/v = 2:8) solution. The addition of CN^? to the sensor p-toluenesulfonyl-2-hydroxy-1-naphthylhydrazone (L3) induced a remarkable color change from pale-yellow to yellow, and green fluorescence changed to yellow. The ¹H NMR titration and DFT calculations suggested that the selective sensing process is based on a nucleophilic addition reaction of cyanide to imine. Test strips based on sensor L3 were fabricated, which could act as a convenient and efficient test kit to detect CN^? for “in-the-field” measurements.     

A highly selective fluorescent chemosensor for Pb2+

A new fluorescent sensor based on rhodamine B for Pb2+ was synthesized. The new fluorescent sensor showed an extreme selectivity for Pb2+ over other metal ions examined in acetonitrile. Upon the addition of Pb2+, an overall emission change of 100-fold was observed, and the selectivity was calculated to be 200 times that of Zn2+. The signal transduction occurs via of reversible CHEF (chelation-enhanced fluorescence) with this inherent quenching metal ion.     

A highly selective and sensitive fluorescent chemosensor for Hg2+ in neutral buffer aqueous solution

A selective and sensitive fluorescent chemosensor for Hg2+, which was composed of two aminonaphthalimide fluorophores and a receptor of 2,6-bis(aminomethyl)pyridine, was synthesized through the reaction of 2,6-bis(chloromethyl)pyridine and N-[2-(2-hydroxyethoxy)ethyl]-4-piperazino-1,8-naphthalimide. The chemosensor showed an about 17-fold increase in fluorescence quantum yield upon addition of 1 equiv of Hg2+ in neutral buffer aqueous solution, and the other common metal ions did not notably disturb the detection of Hg2+.     

A novel 5-mercapto triazole Schiff base as a selective chromogenic chemosensor for Cu2+

A novel colorimetric cation sensor bearing phenol, thiol and HCN groups was designed and synthesized. In a DMSO/H2O (9:1, v/v) solution, the sensor exhibited highly selective recognition of Cu2+ among a range of metal ions tested. In the presence of Cu2+, solutions of the sensor underwent a dramatic color change from colorless to yellow, while the presence of other metal cations such as Zn2+, Pb2+, Cd2+, Ni2+, Co2+, Fe3+, Hg2+, Ag+ and Ca2+ had no effect on the color. The detection limit of the sensor toward Cu2+ is 8.0×10(-7) M and an association constant Ka of 4.3×10(5) M(-1) was measured. The sensing of Cu2+ by this sensor was found to be reversible, with the Cu2+-induced color being lost upon addition of EDTA.     

A highly selective redox, chromogenic, and fluorescent chemosensor for Hg2+ in aqueous solution based on ferrocene-glycine bioconjugates

The synthesis, electrochemical, optical, and metal-cation-sensing properties of ferrocene-glycine conjugates C(30)H(38)O(8)N(8)Fe (2) and C(20)H(24)O(4)N(4)Fe (3) have been documented. Both compounds 2 and 3 behave as very selective redox (ΔE(1/2) = 217 mV for 2 and ΔE(1/2) = 160 mV for 3), chromogenic, and fluorescent chemosensors for Hg(2+) cations in an aqueous environment. The considerable changes in their absorption spectra are accompanied by the appearance of a new low-energy peak at 630 nm (2, ε = 1600 M(-1) cm(-1); 3, ε = 822 M(-1) cm(-1)). This is also accompanied by a strong color change from yellow to purple, which allows a prospective for the "naked eye" detection of Hg(2+) cations. These chemosensors present immense brightness and fluorescence enhancement (chelation-enhanced fluorescence = 91 for 2 and 42 for 3) following Hg(2+) coordination within the limit of detection for Hg(2+) at 7.5 parts per billion.     

Highly sensitive and selective chemosensor for Hg2+ based on the rhodamine fluorophore

A novel tren-based tripodal chemosensor 1 bearing a rhodamine and two tosyl groups was synthesized and its sensing behavior toward metal ions was investigated by UV/vis and fluorescence spectroscopies. Addition of a Hg2+ ion to a CH3CN solution of 1 gave a visual color change as well as significantly enhanced fluorescence, while other ions including Pb2+, Zn2+, Cu2+, Ca2+, Ba2+, Cd2+, Co2+, Mg2+, Ag+, Cs+, Li+, and Na+ induced no or much smaller color/spectral changes, which constituted a Hg2+-selective fluorescent chemosensor (OFF-ON).     

Selective sensing of Cu2+ ion by naphthalene based Schiff base

Research is going on to synthesize materials for acting as sensors of metal ions and are also published in different journals but the cause for sensing has not been clearly explained. In this paper, the reason for selective sensing of Cu²⁺ ions has been explained. A novel Schiff base fluorescent probe 3-[(2-hydroxy-naphthalen-1-ylmethylene)-hydrazono]-butan-2-one oxime (NPTH) was designed and synthesized to use as Cu²⁺ sensor. From our recent experiments, it has been found that only Cu²⁺ among different metal ions has been sensed by the synthesized ligand. The reason for selection and sensing of Cu²⁺ by the ligand was established by different spectroscopic techniques. The detection limit of NPTH was calculated as low as 4.11 ​× ​10^-4M for Cu²⁺. Therefore, these results indicate that sensor NPTH has great prospective to detect Cu²⁺ ion in environmental analysis systems. Density functional theory (DFT) calculations have been done to ascertain the ground state geometry of NPTH.     

A Schiff base fluorescence probe for highly selective turn-on recognition of Zn2+

A simple Schiff base CTS, synthesized between 2-hydroxy-1-naphthaldehyde and 2-benzylthio-ethanamine, was found to be a good turn-on fluorescence probe for the detection of Zn²⁺, due to the restriction of the rotation of the bond between CN and naphthalene ring and/or the blocking of the photo-induced electron transfer (PET) mechanism of the nitrogen atom to naphthalene ring. Excellent selectivity for Zn²⁺ was evidenced, over many other competing ions, including Fe³⁺, Cr³⁺, Ni²⁺, Co²⁺, Fe²⁺,Mn²⁺, Ca²⁺, Hg²⁺, Pb²⁺, Cu²⁺, Mg²⁺, Ba²⁺, Cd²⁺, Ag⁺, Li⁺, K⁺, and Na⁺, in EtOH/HEPES buffer (95:5, v/v, pH = 7.4). It was noteworthy that Cd²⁺ had no interference with Zn²⁺. The stoichiometric complex of CTS-Zn²⁺ was determined to be 2:1 for CTS and Zn²⁺ in molar, based on the Job plot and single crystal X-ray diffraction data. The binding constant of the complex was 85.7 M^?2 with a detection limit of 5.03 × 10^?7 M. The fluorescence bio-imaging capability of CTS to detect Zn²⁺ in live cells was also studied. These results indicated that CTS could serve as a favorable probe for Zn²⁺.     

A highly selective ratiometric chemosensor for Hg based on the anthraquinone derivative with urea groups

Anthraquinone derivatives with different substituents 1-3 were synthesized by introducing the urea group. Their cations' binding properties were investigated by UV-vis absorption spectroscopy. Compared with 1 and 2, 3 with electron-withdrawing group (-NO₂) showed a remarkable absorption change for Hg²⁺ over the other metal ions. The anthraquinone moiety and the N-H fragment of the urea moiety played key roles in sensing Hg²⁺. The different acidity of N-H fragments of the urea moiety, caused by electron push-pull properties of the substituents on the phenyl para position, is the main reason for recognition.     

A novel sensitive turn-on fluorescent Zn2+ chemosensor based on an easy to prepare C3-symmetric Schiff-base derivative in 100% aqueous solution

A C(3)-symmetric Schiff-base example of the new simple, low cost, highly water soluble, and sensitive turn-on fluorescent Zn(2+) chemosensor is described. The sensor was successfully applied to the detection of intracellular Zn(2+). Moreover, the sensor could also serve as a potential recyclable component in sensing materials. Notably, the color change is so obvious that all of the recycling process can be seen clearly by the naked eye.     

A simple Schiff base as selective and sensitive fluorescent-colorimetric hydrazine chemosensor

ABSTRACT

A new fluorescent-colorimetric chemosensor L has been synthesised by Schiff base condensation reaction between 1,8-diaminooctane and 4-nitro-benzaldehyde in very good yields. Its photo-luminescent properties and selective detection properties for hydrazine have been examined. The synthesised chemosensor exhibited highly selective fluorescence on-off response for hydrazine amongst a wide range of different metal cations, anions and amines, along with the bare eye colour change from colourless to yellow based on intermolecular hydrogen-bond interaction. The limit of detection of the chemosensor L was estimated as 9.77 × 10^?8 M or 3.12 × 10^?6 g L^?1 for hydrazine which is extremely below the limit set by the World Health Organization (WHO) and the binding stoichiometry was proposed to be 1 : 2 based on ¹H NMR spectroscopic techniques and the Job’s plot analysis. The proposed sensing mechanism is the hydrogen-bonding interaction which has further been established by Density Functional Theory (Functional Density Theory (DFT)) studies. This recognition feature of sensor L makes it an efficient chemosensor for hydrazine detection in different water samples.     

A highly selective and colorimetric naked-eye chemosensor for Cu2+

A sample and practical colorimetric naked-eye chemosensor 3-nitro-4-ethylenediamido-nitrobenzene (2) for metal cations was designed and synthesized. It displays high selectivity and sensitivity for Cu2+ by the UV absorption which appeared a new peak at 525 nm and color change from yellow to red by naked-eye in CH3OH/H2O pH 7.6.     

A highly selective and sensitive fluorescent chemosensor for Zn^2＋

A new selective Zn^2＋ fluorescent chemosensor, o-vanillin-4-ethoxybenzoylhydrazone （1）, was designed and prepared. Free 1 mainly displayed very weak fluorescence at 480 nm upon excitation at 403 nm. It displayed high selectivity for Zn^2＋ and had a 518- fold fluorescent enhancement upon binding of Zn^2＋, while the other cation ions had only little influence on the fluorescence of 1. Mechanism of enhancement of l＇s fluorescence by Zn^2＋ was briefly discussed.     

A highly selective ratiometric fluorescent chemosensor for Zn2+ ion based on a polyimine macrocycle

A new ratiometric fluorescent chemosensor based on a polyimine macrocycle ligand 1 has been synthesized. The chemosensor can exhibit a pronounced fluorescence response and high selectivity to Zn²⁺ ion over other 15 metal ions, including Cd²⁺. Sensor 1 appears an emission peak at 370 nm. Upon the addition of Zn²⁺ ion, the typical emission peak for 1 at 370 nm is obviously quenched, but a new emission peak at around 470 nm appears and shows a large enhancement due to the formation of a 1:1 Zn²⁺-1 complex. In addition, there is a good linear relationship between the fluorescence ratio I_470nm/I_370nm and the concentration of Zn²⁺, which makes a ratiometric assay of Zn²⁺ ion possible.     

A "turn-on" fluorescent Hg2+ chemosensor based on Ferrier carbocyclization

A "turn-on" fluorescent chemosensor with excellent selectivity and satisfactory sensitivity on Hg(2+) detection in 100% water media has been established employing a carbohydrate based Ferrier carbocyclization reaction. The probe has also presented satisfactory results for the imaging of Hg(2+) ions in cells and organisms.     

A sugar-quinoline fluorescent chemosensor for selective detection of Hg2+ ion in natural water

A selective and sensitive fluorescent sensor for detection of Hg2+ in natural water was achieved by incorporating the well-known fluorophore quinoline group and a water-soluble D-glucosamine group within one molecule.     

A highly selective chemosensor for copper ion based on ICT fluorescence

Simple structural compounds 1 to 3 were synthesized.The presence of Cu²⁺ resulted in the fluorescence and absorption spectra change of 1 and 2,which indicated that 1 and 2 showed a highly selective response to Cu²⁺ over other metal ions.However,3 showed no selectivity for metal ions,which means that the compound could bind with several metal ions,such as,Ni²⁺,Zn²⁺,Cd²⁺.Hg²⁺, Pb²⁺,Fe³⁺,Mg²⁺,Ca²⁺,and Co²⁺,except Cu²⁺ and Ag⁺.The different spectral responses were attributed to the difference in binding sites for 1 and 3.     

Fluorescent chemosensor based on Schiff base for selective detection of zinc(II) in aqueous solution

A chemosensor 1, based on the Schiff base, is easily prepared by reacting tryptophan and 2-hydroxy-1-naphthaldehyde in methanol. The optical properties of 1 are investigated in buffered aqueous solution, which displays specific recognition to Zn²⁺, and especially avoids the interference of Cd²⁺ when 1 is tested against a range of physiological and environmentally relevant metal ions. Such a novel fluorescent probe can also be used to detect Zn²⁺ in live cells.