Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Bis-BODIPY linked-triazole based on catechol core for selective dual detection of Ag⁺ and Hg².

ABSTRACT: Herein, we introduced a new chemosensor, bis-BODIPY linked-triazole based on catechol (BODIPY-OO) prepared by bridging two units of BODIPY fluorophore/triazole binding group with a catechol unit. A solution of this compound displayed 4- and 2-fold enhancements in fluorescence intensity after adding a mole equivalent amount of Ag⁺ and Hg²⁺ ions in methanol media, respectively. ¹H NMR titrations of BODIPY-OO with Ag⁺ and Hg²⁺ suggested that the triazole was involved in the recognition process. BODIPY-OO showed high sensitivity toward Ag⁺ and Hg²⁺ over other metal ions with detection limits of 0.45 μM and 1 μM, respectively. It can also distinguish Hg²⁺ from Ag⁺ by addition of an EDTA. This compound can therefore be employed as practical fluorescent probe for monitoring the presence of Ag⁺ and Hg²⁺ ions.

SUBMITTER: Saiyasombat W

PROVIDER: S-EPMC8694132 | biostudies-literature | 2021 Jan

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Bis-BODIPY linked-triazole based on catechol core for selective dual detection of Ag+ and Hg2.

Saiyasombat Worakrit W Kiatisevi Supavadee S

RSC advances 20210119 6

Herein, we introduced a new chemosensor, bis-BODIPY linked-triazole based on catechol (BODIPY-OO) prepared by bridging two units of BODIPY fluorophore/triazole binding group with a catechol unit. A solution of this compound displayed 4- and 2-fold enhancements in fluorescence intensity after adding a mole equivalent amount of Ag+ and Hg2+ ions in methanol media, respectively. 1H NMR titrations of BODIPY-OO with Ag+ and Hg2+ suggested that th ...[more]

PMID: 35424275

Similar Datasets

1,3-Alternate Calix[4]arene Functionalized With Pyrazole and Triazole Ligands as a Highly Selective Fluorescent Sensor for Hg2+ and Ag+ Ions.

Project description:We report here the synthesis of a 1,3-alternate calix[4]arene 8, with bis-pyrazolylmethylpyrenes on the one end and bis-triazolylmethylphenyls on the other end, as a homoditropic fluorescent sensor for both Hg2+ and Ag+ ions. Calix[4]arene 3, with lower-rim bis-pyrazolylmethylpyrenes in cone conformation, was also synthesized as a control compound. UV-Vis and fluorescence spectra were used for metal ions screening, and we found that both ligands 8 and 3 showed strong excimer emission of pyrenes when they are as a free ligand in CHCl3/MeOH (v/v, 3:1) solution; however, they both showed a high selectivity toward Hg2+ and Ag+ ions with strong fluorescence quenching and yet with different binding ratios. The fluorescence of ligand 8 was strongly quenched by Hg2+ but was only partially quenched by Ag+ ions; however, the fluorescence of ligand 3 was strongly quenched by Hg2+, Ag+, and Cu2+ ions. Job plot experiments showed that ligand 8 formed a 1:2 complex with both Hg2+ and Ag+ ions; ligand 3 formed a 1:1 complex with Hg2+, but it formed a 2:3 complex with Ag+. The binding constant of ligand 3 with Hg2+ and Ag+ ions was determined by the Benesi-Hildebrand plot of UV-vis titration experiments to be 2.99 × 103 and 3.83 × 103 M-1, respectively, while the association constant of ligand 8 with Hg2+ and Ag+ was determined by Hill plot to be 1.46 × 1012 and 9.24 × 1011 M-2, respectively. Ligand 8 forms a strong complex with either two Hg2+ or two Ag+ ions using both the upper and lower rims of the 1,3-alternate calix[4]arene as the binding pockets; hence, it represents one of the highly selective fluorescent sensors for the homoditropic sensing of Hg2+ and Ag+ ions.

| S-EPMC7688584 | biostudies-literature

Unconventional OFF-ON Response of a Mono(calix[4]arene)-Substituted BODIPY Sensor for Hg2+ through Dimerization Reversion.

Project description:A new selective fluorogenic chemosensor for Hg2+, which combines a calixarene derivative with a BODIPY core as a fluorescent reporter, is described. The remarkable change in its fluorogenic properties in DMSO and CHCl3 has been analyzed. A study of its spectral properties on dilution, along with molecular modeling studies, allowed us to explain that this behavior involves the formation of a J-dimer, as well as how the sensing mechanism of Hg2+ proceeds.

| S-EPMC9835786 | biostudies-literature

Bis-Pyridine-Based Organogel with AIE Effect and Sensing Performance towards Hg2.

Project description:A novel gelator (1) based on a bis-pyridine derivative was designed and synthesized, which could form stable gels in methanol, ethanol, acetonitrile, ethyl acetate, DMF/H2O (4/1, v/v) and DMSO/H2O (4/1, v/v). The self-assembly process of gelator 1 was studied by field emission scanning electron microscopy (FESEM), UV-vis absorption spectroscopy, fluorescence emission spectroscopy, Fourier transform infrared spectroscopy (FT-IR), X-ray powder diffraction and a water contact angle experiment. Gelator 1 exhibited obvious AIE behavior. On the base of its AIE, the gel of 1 could detect Hg2+, which resulted in fluorescence quenching and a gel-sol transition. 1H NMR titration experiments with Hg2+ revealed that the metal coordination interaction induced the fluorescence quenching and the breakdown of the noncovalent interaction in the gel system. This research provides a new molecular mode for designing a functional self-assembly gel system.

| S-EPMC9331886 | biostudies-literature

Directed Assembly of Au Nanostar@Ag Satellite Nanostructures for SERS-Based Sensing of Hg2+ Ions.

Project description:Embedding Raman reporters within nanosized gaps of metallic nanoparticles is an attractive route for surface-enhanced Raman spectroscopy (SERS) applications, although often this involves complex synthesis procedures that limit their practical use. Herein, we present the tip-selective direct growth of silver satellites surrounding gold nanostars (AuNSt@AgSAT), mediated by a dithiol Raman reporter 1,4-benzenedithiol (BDT). We propose that BDT is embedded within nanogaps which form between the AuNSt tips and the satellites, and plays a key role in mediating the satellite growth. Not only proposing a rationale for the mechanistic growth of the AuNSt@AgSAT, we also demonstrate an example for its use for the detection of Hg2+ ions in water. The presence of Hg2+ resulted in amalgamation of the AuNSt@AgSAT, which altered both its structural morphology and Raman enhancement properties. This provides a basis for the detection where the Raman intensity of BDT is inversely proportional to the Hg2+ concentrations. As a result, Hg2+ could be detected at concentrations as low as 0.1 ppb. This paper not only provides important mechanistic insight into the tip-selective direct growth of the anisotropic nanostructure but also proposes its excellent Raman enhancement capability for bioimaging as well as biological and chemical sensing applications.

| S-EPMC10294701 | biostudies-literature

A one-dimensional HgII coordination polymer based on bis-(pyridin-3-ylmeth-yl)sulfane.

Project description:The reaction of mercury(II) chloride with bis-(pyridin-3-ylmeth-yl)sulfane (L, C12H12N2S) in methanol afforded the title crystalline coordination polymer catena-poly[[di-chlorido-mercury(II)]-μ-bis-(pyridin-3-ylmeth-yl)sulfane-κ2N:N'], [HgCl2L] n . The asymmetric unit consists of one HgII cation, one L ligand and two chloride anions. Each HgII ion is coordinated by two pyridine N atoms from separate L ligands and two chloride anions. The metal adopts a highly distorted tetra-hedral geometry, with bond angles about the central atom in the range 97.69 (12)-153.86 (7)°. Each L ligand bridges two HgII ions, forming an infinite -(Hg-L) n - zigzag chain along the b axis, with an Hg⋯Hg separation of 10.3997 (8) Å. In the crystal, adjacent chains are connected by inter-molecular C-H⋯Cl hydrogen bonds, together with Hg-Cl⋯π inter-actions [chloride-to-centroid distance = 3.902 (3) Å], that form between a chloride anion and the one of the pyridine rings of L, generating a two-dimensional layer extending parallel to (101). These layers are further linked by inter-molecular C-H⋯π hydrogen bonds, forming a three-dimensional supra-molecular network.

| S-EPMC5730242 | biostudies-literature

Triazole-Linked Quinoline Conjugate of Glucopyranose: Selectivity Comparison among Zn2+, Cd2+, and Hg2+ Based on Spectroscopy, Thermodynamics, and Microscopy, and Reversible Sensing of Zn2+ and the Structure of the Complex Using DFT.

Project description:A water-soluble triazole-linked quinoline conjugate of glucopyranose (L) has been synthesized and characterized, and its single-crystal X-ray diffraction (XRD) structure has been established. Binding of L toward different biologically relevant metal ions has been studied using fluorescence and absorption spectroscopy in HEPES buffer at pH 7.4. The conjugate L detects Zn2+ and Cd2+ with 30 ± 2 and 14 ± 1-fold fluorescence enhancement, respectively, but in the case of Hg2+, only a fluorescence quench was observed. The stoichiometry of the complex is 1:2 metal ion to the ligand in the case of Zn2+ and Cd2+ resulting in [Zn(L)2] and [Cd(L)2], and it is 1:1 in the case of Hg2+, as confirmed from their electrospray ionization mass spectrometry (ESIMS) spectra. Zn2+ shows greater exothermicity over Cd2+, whereas Hg2+ shows endothermicity , which supports the differences in their binding strength and the nature of the corresponding complex. L exhibits rod-shaped particles and upon complexation with Zn2+, it exhibits sphere-like morphological features in scanning electron microscopy (SEM) images. However, clustered aggregates are observed in Cd2+, whereas the [HgL] complex exhibits small fused spherical structures, and therefore the signature of these ions is seen in microscopy images. The computational studies revealed that the syn-[Zn(L)2] complex is stabilized by 9.7 kcal mol-1 more than that in the case of anti-[Zn(L)2] owing to the formation of hydrogen bonds between the two glucosyl moieties within the syn-complex. Among the anions studied, [Zn(L)2] is sensitive and selective toward the phosphate ion (H2PO4 -) with a minimum detection limit of 16 ± 2 ppb. Similarly, the [HgL] can act as a secondary sensor for CN- while also exhibiting reversibility. Based on the input-output characteristics, INHIBIT logic gate was built in the case of Zn2+ vs H2PO4 - and IMPLICATION logic gate was built in the case of Hg2+ vs CN-.

| S-EPMC6640762 | biostudies-literature

Aqueous synthesis of functionalized copper sulfide quantum dots as near-infrared luminescent probes for detection of Hg2+, Ag+ and Au3.

Project description:Stable water-soluble copper sulfide(Cu2S) quantum dots(QDs) with near-infrared emission were synthesized using N-acetyl-L-cysteine(NAC) as a modifier in aqueous solution and nitrogen atmosphere at room temperature. The product was characterized by TEM, XRD, XPS, FT-IR, FL and UV-VIS spectrometers. Effects of preparation conditions such as pH values, the molar ratio of reactants, temperature, and metal ions on the fluorescence properties of Cu2S QDs were discussed. Under optimal conditions, the prepared Cu2S QDs with average diameter about 2-5 nm show a near-infrared emission at 770 nm with the excitation wavelength of 466 nm, and have a good detection sensitivity for ions of Hg2+, Ag+ and Au3+, based on the characteristic of fluorescence quenching. The fluorescence quenching mechanism was proposed via electron transfer with cation exchange, which based on the theory of Hard-Soft-Acid-Base (HSAB) and Ksp value of metal-sulfide.

| S-EPMC5597581 | biostudies-literature

Triazole-based novel bis Schiff base colorimetric and fluorescent turn-on dual chemosensor for Cu2+ and Pb2+: application to living cell imaging and molecular logic gates.

Project description:A triazole-based novel bis Schiff base colorimetric and fluorescent chemosensor (L) has been designed, synthesized and characterized by elemental analysis, 1H-NMR, ESI-MS, FTIR spectra and DFT studies. The receptor L showed selective and sensitive colorimetric sensing ability for Cu2+ and Pb2+ ions by changing color from colorless to yellow and light yellow respectively in CH3OH-tris-buffer (1 : 1, v/v). However, it displayed strong fluorescence enhancement upon the addition of both Cu2+ and Pb2+ ions, attributed to the blocking of PET. The fluorometric detection limits for Cu2+ and Pb2+ were found to be 12 × 10-7 M and 9 × 10-7 M and the colorimetric detection limits were 3.7 × 10-6 M and 1.2 × 10-6 M respectively; which are far below the permissible concentration in drinking water determined by WHO. Moreover, it was found that chemosensor L worked as a reversible fluorescence probe towards Cu2+ and Pb2+ ions by the accumulation of S2- and EDTA respectively. Based on the physicochemical and analytical methods like ESI-mass spectrometry, Job plot, FT-IR, 1H-NMR spectra and DFT studies the detection mechanism may be explained as metal coordination, photoinduced electron transfer (PET) as well as an internal charge transfer (ICT) process. The sensor could work in a pH span of 4.0-12.0. The chemosensor L shows its application potential in the detection of Cu2+ and Pb2+ in real samples, living cells and building of molecular logic gate.

| S-EPMC9070313 | biostudies-literature

"Turn on" and label-free core-shell Ag@SiO2 nanoparticles-based metal-enhanced fluorescent (MEF) aptasensor for Hg(2+).

Project description:A turn on and label-free fluorescent apasensor for Hg(2+) with high sensitivity and selectivity has been demonstrated in this report. Firstly, core-shell Ag@SiO2 nanoparticles (NPs) were synthetized as a Metal-Enhanced Fluorescent (MEF) substrate, T-rich DNA aptamers were immobilized on the surface of Ag@SiO2 NPs and thiazole orange (TO) was selected as fluorescent reporter. After Hg(2+) was added to the aptamer-Ag@SiO2 NPs and TO mixture buffer solution, the aptamer strand can bind Hg(2+) to form T-Hg(2+)-T complex with a hairpin structure which TO can insert into. When clamped by the nucleic acid bases, the fluorescence quanta yield of TO will be increased under laser excitation and emitted a fluorescence emission. Furthermore, the fluorescence emission can be amplified largely by the MEF effect of the Ag@SiO2 NPs. The whole experiment can be finished within 30 min and the limit of detection is 0.33 nM even with interference by high concentrations of other metal ions. Finally, the sensor was applied for detecting Hg(2+) in different real water samples with satisfying recoveries over 94%.

| S-EPMC4377581 | biostudies-other

Selective determination of Ag+ in the presence of Cd2+, Hg2+ and Cu2+ based on their different interactions with gold nanoclusters.

Project description:In this work, a fluorescence method was developed for selective detection of Ag+ in the presence of Cd2+, Hg2+, and Cu2+ based on gold nanoclusters (AuNCs). That is, bovine serum albumin (BSA) templated AuNCs with double emission peaks were synthesized using BSA as a protective agent. AuNCs with uniform distribution and average size between 2.0 and 2.2 nm were synthesized using a green and simple method, and showed bright orange-red fluorescence under ultraviolet light. AuNCs have two emission peaks at 450 nm and 630 nm with an excitation wavelength of 365 nm. Under alkaline conditions, Cd2+ can combine with the surface sulfhydryl groups of BSA-AuNCs to form Cd-S bonds, which cause AuNCs to aggregate, resulting in an increase in fluorescence intensity at 630 nm. Conversely, due to the d10-d10 metal affinity interaction, the addition of Hg2+ can reduce the fluorescence peak at 630 nm. Ag+ was reduced to Ag0 by gold nuclei in AuNCs, forming a stable hybrid Au@ AgNCs species with blue-shifted and enhanced fluorescence. Finally, the paramagnetic behavior of Cu2+ combined with BSA causes the excited electrons of the gold cluster to lose their energy via ISC, eventually leading to simultaneous quenching of the two emission peaks. The results show that the limit of detection (LOD) of Ag+, Hg2+, Cd2+ and Cu2+ is 1.19 μM, 3.39 μM, 1.83 μM and 5.95 μM, respectively.

| S-EPMC9056666 | biostudies-literature