Metal Chelation Chemistry

Lee, Dongwhan

doi:10.1002/9781118019580.ch4

Cited by 4 publications

(4 citation statements)

References 117 publications

(128 reference statements)

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“…The fluorescence was monitored at the emission maximum of BPT fluorescence. Slope of the plot yielded the K SV value as 6.96 × 10 4 mol -1 dm 3 implying that the fluorescence quenching occurred because of binding of Cu(II) ion with BPT and not through diffusional collision between the two interacting species.…”

Section: O-h H8 H10 H12 H13 H11 O-h H8 H10 H12 H11 H13mentioning

confidence: 97%

“…3With the metal-chelator complexes, the potential exists to "tune" the selectivity and sensitivity of the probes by (i) taking advantage of cation affinity for specific atoms and (ii) controlling the size of the binding site through the intentional placement of the coordinating moieties in the sensors. (3) In most cases, a chelate arises from covalent or coordinate bonds between the metal and donorfunctional groups containing sulfur, nitrogen and/ or oxygen atoms. (4) Metal cations are of biological and ecological importance.…”

Section: Introductionmentioning

confidence: 99%

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Spectroscopic investigation of bis-appended 1,2,3-triazole probe for the detection of Cu(II) ion

Ghosh

Rhodes

Winder

et al. 2017

Journal of Molecular Structure

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A novel bis-1,4-disubstituted-1,2,3-triazole chemosensor, accessed with "Click Chemistry", was probed for its recognition of metal ions. The interaction of the sensor with various cation analytes was investigated by 1 H-NMR, UV-Vis absorption and fluorescence spectroscopy. The bis-triazole is selective for Cu(II) with a detection limit in the micromolarconcentration range and a clear to yellow colorimetric response that is exclusive to that ion is observed. The stoichiometry of probe to Cu(II), 2 : 1, was determined with Job's plots based on titration studies using UV-absorption and 1 H-NMR spectroscopy. Computational and spectroscopic investigations revealed that the sensor binds to Cu(II) via its triazole units. Keywords: , there are less reports for bis-triazole sensors that provide a colorimetric signal.(43) Additionally, in many instances the bistriazole sensors fail to respond exclusively to Cu(II).(31, 34, 37, 38) Herein, we report the synthesis of a novel bis-1,2,3triazole sensor appended with phenolic groups, (2,2-bis((1-(2hydroxyphenyl)-1H-1,2,3-triazol-4-yl)methyl)-5,5dimethylcyclohexane-1,3-dione) (BPT) (Scheme 1). BPT exhibits a selective colorimetric response to copper(II), clear to yellow. To verify the selectivity, BPT was screened against an series of metal ions

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Section: O-h H8 H10 H12 H13 H11 O-h H8 H10 H12 H11 H13mentioning

confidence: 97%

Section: Introductionmentioning

confidence: 99%

Spectroscopic investigation of bis-appended 1,2,3-triazole probe for the detection of Cu(II) ion

Ghosh

Rhodes

Winder

et al. 2017

Journal of Molecular Structure

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“…43–45 Many macrocyclic ligands bind lanthanide ions with extraordinary selectivity and stability, 46 and resultant complexes are highly water soluble, kinetically inert at neutral pH and cell-permeable. 47,48 We selected DO2A ( 1,4,7,10 -tetraazacyclododecane- 1,7 -bisacetate) as the ancillary ligand of choice 49 with the goal of improving bacterial spore detection based on Tb 3+ -DPA luminescence (Figure 2).…”

Section: Ancillary Ligand-induced Enhancementmentioning

confidence: 99%

“…Macrocyclic ligands, which have a semirigid backbone ring structure and variable ring diameter and functionalization, have a hydrophilic metal-ion binding cavity that is shielded from the environment by its lipophilic envelope. − Many macrocyclic ligands bind lanthanide ions with extraordinary selectivity and stability, and resultant complexes are highly water-soluble, kinetically inert at neutral pH, and cell-permeable. , We selected DO2A (1,4,7,10-tetraazacyclododecane-1,7-bisacetate) as the ancillary ligand of choice with the goal of improving bacterial spore detection based on Tb 3+ -DPA luminescence (Figure ).…”

Section: Ancillary Ligand-induced Enhancementmentioning

confidence: 99%

Enhancement of Anion Binding in Lanthanide Optical Sensors

Cable

Kirby²,

Gray

et al. 2013

Acc. Chem. Res.

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In the design of molecular sensors, researchers exploit binding interactions that are usually defined in terms of topology and charge complementarity. The formation of complementary arrays of highly cooperative, noncovalent bonding networks facilitates protein-ligand binding, leading to motifs such as the ‘lock-and-key.’ Synthetic molecular sensors often employ metal complexes as key design elements as a way to construct a binding site with the desired shape and charge to achieve target selectivity. In transition metal complexes, coordination number, structure and ligand dynamics are governed primarily by a combination of inner-sphere covalent and outer-sphere noncovalent interactions. These interactions provide a rich variable space that researchers can use to tune structure, stability and dynamics. In contrast, lanthanide(III)-ligand complex formation and ligand-exchange dynamics are dominated by reversible electrostatic and steric interactions, because the unfilled f shell is shielded by the larger, filled d shell. Luminescent lanthanides such as terbium, europium, dysprosium and samarium display many photophysical properties that make them excellent candidates for molecular sensor applications. Complexes of lanthanide ions act as receptors that exhibit a detectable change in metal-based luminescence upon binding of an anion. In our work on sensors for detection of dipicolinate, the unique biomarker of bacterial spores, we discovered that the incorporation of an ancillary ligand (AL) can enhance binding constants of target anions to lanthanide ions by as much as two orders of magnitude. In this Account, we show that selected ALs in lanthanide/anion systems greatly improve sensor performance for medical, planetary science and biodefense applications. We suggest that the observed anion binding enhancement could result from an AL-induced increase in positive charge at the lanthanide ion binding site. This effect depends on lanthanide polarizability, which can be established from the ionization energy of Ln3+ → Ln4+. These results account for the order Tb3+ > Dy3+ > Eu3+ ≈ Sm3+. As with many lanthanide properties, ranging from hydration enthalpy to vaporization energy, this AL-induced enhancement shows a large discrepancy between Tb3+ and Eu3+ despite their similarity in size, a phenomenon known as the ‘gadolinium break.’ This discrepancy, based on the unusual stabilities of the Eu2+ and Tb4+ oxidation states, results from the half-shell effect, as both of these ions have half-filled 4f-shells. The high polarizability of Tb3+ explains the extraordinarily large increase in the binding affinity of anions for terbium compared to other lanthanides. We recommend that researchers consider this AL-induced enhancement when designing lanthanide-macrocycle optical sensors. Ancillary ligands also can reduce the impact of interfering species such as phosphate) commonly found in environmental and physiological samples.

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BOIMPY: Fluorescent Boron Complexes with Tunable and Environment‐Responsive Light‐Emitting Properties

Lee

Park

Cho

et al. 2016

Chemistry A European J

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A series of air-stable boron complexes 1-5 were prepared by using N-aryl iminopyrrolide ligands. Designed as minimalist structural mimics of the privileged BODIPY motif, these new BOIMPY (BOron complexes of IMinoPYrrolide ligands) fluorophores feature low molecular symmetry that promotes emission from CT-type excited states with large Stokes shifts and little self-quenching. Through comparative studies on the homologous set of compounds 1-4, we have confirmed that a delicate interplay between conformational twisting and donor-acceptor interaction dictates the mechanism of de-excitation, which responds sensitively to solvent polarity as well as protonation states. Over a wide visible spectral range, the structure-dependent light-emitting properties of BOIMPY molecules are well manifested, even in the solid-state. In order to exploit the environment-sensitive nature of CT-type emission, the BOIMPY motif was elaborated further into a bioprobe molecule 5. Live-cell fluorescence imaging studies have established that 5 is localized exclusively at lipid droplets to produce well-resolved staining patterns without affecting cell viability. These findings promise future elaboration of BOIMPY-based functional molecules for applications in biological imaging, chemical sensing, and molecular switching.

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Metal Chelation Chemistry

Cited by 4 publications

References 117 publications

Spectroscopic investigation of bis-appended 1,2,3-triazole probe for the detection of Cu(II) ion

Spectroscopic investigation of bis-appended 1,2,3-triazole probe for the detection of Cu(II) ion

Enhancement of Anion Binding in Lanthanide Optical Sensors

BOIMPY: Fluorescent Boron Complexes with Tunable and Environment‐Responsive Light‐Emitting Properties

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