Water-Soluble Sulfonate Schiff-Base Ligands as Fluorescent Detectors for Metal Ions in Drinking Water and Biological Systems

Reimann, Meredith J.; Salmon, Duncan; Horton, Jacqueline T.; Gier, Eric C.; Jefferies, Latisha R.

doi:10.1021/acsomega.8b02750

Cited by 47 publications

(21 citation statements)

References 53 publications

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“…25−27 On the other hand, Schiff base molecules have good complexation for most transition metal ions since the lone pair electrons contained in nitrogen atoms and carbon–nitrogen double bonds can be used as electron donors to coordinate with most metal ions to form stable complexes. 17,18 The introduction of a naphthalene ring with a planar structure, large volume, and strong rigidity increases the π conjugate of Schiff base molecules, thereby facilitating assembly with the host resin material. When chelated with a metal ion, the phenolic hydroxyl oxygen atom on the naphthalene ring of the Schiff base is also involved in coordination and can be complexed with a plurality of transition metal ions to form a more stable coordinated chelate.…”

Section: Resultsmentioning

confidence: 99%

“…16 A Schiff base is a kind of compound with an imine (−C=N) structure formed by the reaction of active carbonyl and amino compounds in the molecule and can form stable complexes with transition metal elements. 17,18 Schiff base compounds and their metal complex compounds have wide applications in medicine, catalysis, and analytical chemistry. 19−21 Schiff bases, especially some aromatic Schiff bases, tend to form stable complexes with copper due to the presence of −C=N double bonds and −OH group of the aromatic ring.…”

Section: Introductionmentioning

confidence: 99%

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Self-Assembled Naphthylidene-Containing Schiff Base Anchored Polystyrene Nanocomposites Targeted for Selective Cu(II) Ion Removal from Wastewater

et al. 2019

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Self-assembled composite adsorbents that combine the controllability of self-assembly with a mild operation process are promising for removal of heavy metal ions in wastewater. The design and preparation of functionalized composite adsorbent materials with multiple-site adsorption ability remain the most attractive in effectively removing heavy metal ions. Inspired by the macroporous structure of charged polystyrene (PS) resin and chelation of Schiff bases with heavy metal ions, smart composite adsorbents are constructed based on the combination and synergistic effect of multiple hydrophobic, π–π stacking, and electrostatic noncovalent interactions between polystyrene resin and naphthylidene-containing Schiff base (NSB). The resulting hybrid nanomaterials (PS-NSB) have uniform porous structures and well-defined and multiple target sites. These properties promote diffusion of the target ion, increase the binding site, and enhance the removal efficacy. This study offers a new strategy to harness a self-assembled Schiff base with integrated flexibility and multifunctions to enhance target metal ion specific binding and removal effects, highlighting opportunities to develop smart composite adsorbents.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Self-Assembled Naphthylidene-Containing Schiff Base Anchored Polystyrene Nanocomposites Targeted for Selective Cu(II) Ion Removal from Wastewater

et al. 2019

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“…In recent years, flexible ligands may provide more possibilities for constructing unique frameworks due to their free conformation. [1][2][3][4] It is found that some factors such as the types of metal salts and ligand structures may affect the construction of "multidecker" complexes. There has been considerable interest in multinuclear selfassemblies [5][6][7][8] designed and synthesized by transition metal ions and organic ligands.…”

Section: Introductionmentioning

confidence: 99%

Construction of novel hexanuclear Co(II) and dinuclear Ni(II) bis(salamo)‐type complexes

Feng

et al. 2021

Applied Organom Chemis

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Two novel homomultinuclear complexes [Co 6 (L) 2 (μ-OAc) 4 ]Á2CHCl 3 ÁCH 3 COCH 3 (1) and [Ni 2 (L)(H 2 O) 2 (Py) 2 ]Á2CHCl 3 (2) with a newly designed rigid bis(salamo)-type tetraoxime ligand (H 4 L) were synthesized and characterized by elemental analyses, Fourier transform infrared (FT-IR) spectra, UV-Vis absorption spectra, and X-ray single-crystal diffractions. Complex 1 is a novel triple-decker symmetrical six-core cluster structure with twofold axis and inversion center. The Co(II) atoms were sandwiched between the bis(salamo)type ligands and possess two different geometries of distorted tetragonal pyramid and octahedron, respectively. Complex 2 possesses a dinuclear structure and the Ni(II) atoms are located in the N 2 O 2 cavities of the ligand, and axial coordination atoms come from the coordinated water and pyridine molecules. Both Ni(II) atoms adopt distorted octahedral geometries. The interactions were quantitatively determined by Hirshfeld surfaces analyses of complexes 1 and 2. The coordination ratios were determined by studying the fluorescence properties of complexes 1 and 2. The results of fluorescence titration experiment show that the metals to ligand binding ratios are 6:2 and 2:1 for complexes 1 and 2, respectively.

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“…Moreover, Schiff bases bearing a salicylidene moiety are also used as chemosensors for sensing of specific ions. In addition, some derivatives also show NLO activity [25,[34][35][36][37].…”

Section: Introductionmentioning

confidence: 99%

Styryl-based new organic chromophores bearing free amino and azomethine groups: synthesis, photophysical, NLO, and thermal properties

Putra¹,

Çakmaz²,

Seferoğlu³

et al. 2020

Beilstein J. Org. Chem.

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Herein we report the synthesis and characterization of a new series of styryl-based push-pull dyes containing a free amino group and their Schiff base derivatives. The dyes include the dicyanomethylene group as an acceptor and different para-substituted alkylamines as donors. Morever as a proton-sensitive group a pyridin-2-yl substituent was attached to the para-position of the phenyl moiety in both series of compounds. The photophysical properties of the dyes were examined in various solvents with different polarities and showed absorption in the visible region and green-red emission with low quantum yields. The absorption and the emission maxima were shifted bathocromically by increasing the solvent’s polarity. However, there was no correlation with the polarity parameters of the solvents. The pH-sensitive properties of all prepared Schiff bases were examined against TBAOH in DMSO, via deprotonation of the OH group in the salicylidene moiety and their reverse protonation was also investigated using TFA. The Schiff bases exhibited a bathochromic shift upon the addition of TBAOH to their solutions in DMSO. Therefore, they showed potential to be utilized as colorimetric and luminescence pH sensors. The second-order nonlinear optical (NLO) responses of the dyes were measured by the electric field-induced second harmonic (EFISH) generation method. The highest μβ values were obtained for the dyes bearing the julolidine donor as 1430 × 10−48 esu (for free amino derivative) and 1950 × 10−48 esu (for Schiff base derivative), respectively. The structural and electronic properties of the dyes as well as their NLO properties were further studied using DFT calculations. The thermal stabilities of all dyes were evaluated by thermogravimetric analysis (TGA). The TGA data showed that all dyes were thermally stable up to 250 °C.

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Water-Soluble Sulfonate Schiff-Base Ligands as Fluorescent Detectors for Metal Ions in Drinking Water and Biological Systems

Cited by 47 publications

References 53 publications

Self-Assembled Naphthylidene-Containing Schiff Base Anchored Polystyrene Nanocomposites Targeted for Selective Cu(II) Ion Removal from Wastewater

Self-Assembled Naphthylidene-Containing Schiff Base Anchored Polystyrene Nanocomposites Targeted for Selective Cu(II) Ion Removal from Wastewater

Construction of novel hexanuclear Co(II) and dinuclear Ni(II) bis(salamo)‐type complexes

Styryl-based new organic chromophores bearing free amino and azomethine groups: synthesis, photophysical, NLO, and thermal properties

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