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Three New Metal Complexes with Imidazole-Containing Tripodal Ligands as Fluorophores for Nitroaromatics- and Ion-Selective Sensing.

ABSTRACT: Three new metal-organic complexes [Cd(TIPA)(suc)_0.5(NO₃)·1/2H₂O]_n (1), [Ni(TIPA)(tda)_0.5(H₂O)·1/4H₂O]_n (2) and [Cd(TIPA)(tda)_0.5·11/2H₂O] (3) were synthesized via rigid tripodal ligand tris(4-(1H-imidazol-1-yl)phenyl)amine (TIPA) and three dicarboxylic acids; either succinic acid (H₂suc) or 2,5-thiophenedicarboxylic acid (H₂tda). Crystallographic data for 1 - 3 reveal three-dimensional (3D) networks and channels in the structures. The structure of 2 is unique featuring an interpenetrating 2D network, 2D + 2D ? 3D, with the two associated 2D networks existing in two opposite spiral channels. TGA plots exhibit a loss of mass corresponding to the loss of the solvated water molecules in the 100 - 200 °C temperature region and begin to lose additional fragments only at T > 300 °C revealing the robust nature of the 3D framework in the complexes. The metal-organic frameworks (MOFs) are screened for their potential application in the detection and removal of environmentally hazardous industrial pollutants. Fluorescence emission spectra for 1 and 2 show that the two MOFs are capable of sensing nitrobenzene (NB), with the nickel complex 2 exhibiting significantly higher sensing ability. Powder XRD data measured for 1 and 2 and those of NB-treated 1 and 2 show significant differences in their patterns, providing further support for the strong interaction between the MOF complexes and NB. The fluorescence emission observed for 1 is more effectively quenched by the presence of Fe³⁺ than the series of 17 other metal ions investigated. Complex 3 possesses some ability to adsorb inorganic pollutants.

SUBMITTER: Huo J

PROVIDER: S-EPMC7453589 | biostudies-literature | 2020 Mar

REPOSITORIES: biostudies-literature

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Three New Metal Complexes with Imidazole-Containing Tripodal Ligands as Fluorophores for Nitroaromatics- and Ion-Selective Sensing.

Huo Jianqiang J Li Haiqiang H Yu Donghui D Arulsamy Navamoney N

Inorganica chimica acta 20191202

Three new metal-organic complexes [Cd(TIPA)(suc)0.5(NO3)·1/2H2O]n (1), [Ni(TIPA)(tda)0.5(H2O)·1/4H2O]n (2) and [Cd(TIPA)(tda)0.5·11/2H2O] (3) were synthesized via rigid tripodal ligand tris(4-(1H-imidazol-1-yl)phenyl)amine (TIPA) and three dicarboxylic acids; either succinic acid (H2suc) or 2,5-thiophenedicarboxylic acid (H2tda). Crystallographi ...[more]

PMID: 32863422

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Project description:Cuprous and cupric complexes with the new imidazolyl containing tripodal tetradentate ligands {L(MIm), (1H-imidazol-4-yl)-N,N-bis((pyridin-2-yl)methyl)methanamine, and L(EIm), 2-(1H-imidazol-4-yl)-N,N-bis((pyridin-2-yl)methyl)ethanamine}, have been investigated to probe differences in their chemistry, especially in copper(I)-dioxygen chemistry, compared to that already known for the pyridyl analogue TMPA, tris(2-pyridyl)methyl)amine. Infrared (IR) stretching frequencies obtained from carbon monoxide adducts of [(L(MIm))Cu(I)](+) (1a) and [(L(EIm))Cu(I)](+) (2a) show that the imidazolyl donor is stronger than its pyridyl analogue. Electrochemical data suggest differences in the binding constant of Cu(II) to L(EIm) compared to TMPA and L(MIm), reflecting geometric changes. Oxygenation of [(L(MIm))Cu(I)](+) (1a) in 2-methyltetrahydrofuran (MeTHF) solvent at -128 degrees C leads to an intensely purple colored species with a UV-vis spectrum characteristic of an end-on bound peroxodicopper(II) complex [{(L(MIm))Cu(II)}(2)(mu-1,2-O(2)(2-))](2+) (1b(P)) {lambda(max) = 528 nm}, very similar to the previously well characterized complex [{(TMPA)Cu(II)}(2)(mu-1,2-O(2)(2-))](2+) {lambda(max) = 520 nm (epsilon = 12 000 M(-1) cm(-1)), in MeTHF; resonance Raman (rR) spectroscopy: nu(O-O) = 832 (Delta((18)O(2)) = -44) cm(-1)}. In the low-temperature oxygenation of 2a, benchtop (-128 degrees C) and stopped-flow (-90 degrees C) experiments reveal the formation of an initial superoxo-Cu(II) species [(L(EIm))Cu(II)(O(2)(*-))](+) (2b(S)), lambda(max) = 431 nm in THF) . This converts to the low-temperature stable peroxo complex [{(L(EIm))Cu(II)}(2)(mu-1,2-O(2)(2-))](2+) (2b(P)) {rR spectroscopy: nu(O-O) = 822 (Delta((18)O(2)) = -46) cm(-1)}. Complex 2b(P) possess distinctly reduced Cu-O and O-O stretching frequencies and a red-shifted UV-vis feature {to lambda(max) = 535 nm (epsilon = 11 000 M(-1) cm(-1))} compared to the TMPA analogue due to a distortion from trigonal bipyramidal (TBP) to a square pyramidal ligand field. This distortion is supported by the structural characterization of related ligand-copper(II) complexes: A stable tetramer cluster complex [(mu(2)-L(EIm-))(4)(Cu(II))(4)](4+), obtained from thermal decomposition of 2b(P) (with formation of H(2)O(2)), also exhibits a distorted square pyramidal Cu(II) ion geometry as does the copper(II) complex [(L(EIm))Cu(II)(CH(3)CN)](2+) (2c), characterized by X-ray crystallography and solution electron paramagnetic resonance (EPR) spectroscopy.

Project description:Novel lanthanide (Ln) compounds [Ln(L)2]Cl.xH2O (Ln = La3+, Ce3+, Sm3+) containing aromatic N,O-chelate ligands [HL1 = 4-amino-2-(1H-benzimidazol-2-yl)phenol; HL2 = 5-amino-2-(1H-benzimidazol-2-yl)phenol] have been synthesized and structurally characterized by elemental analysis, NMR and IR spectroscopy, molar conductance measurements, and mass spectrometry (MS). The spectroscopic data suggested that the benzimidazolyl-phenol ligands act as N,O-chelate ligands through the iminic nitrogen and phenolic oxygen atoms. Elemental analysis indicated that lanthanide compounds were formed in a 1:2 stoichiometry (metal:ligand). In vitro biological evaluation was carried out using these complexes, exhibiting moderate cytotoxicity against six different human tumor cell lines (U251, human glioblastoma; HCT-15, colorectal carcinoma; MCF-7, breast epithelial adenocarcinoma; PC-3, prostate cancer; K562, myelogenous leukemia; SKLU-1, lung carcinoma) and lower toxicity against a non-cancerous cell line (COS-7, primate kidney). In addition, the antibacterial activity of the compounds was assessed against two gram-positive strains (Staphylococcus aureus ATCC 25923, Listeria monocytogenes ATCC 19115) and two gram-negative strains (Escherichia coli ATCC 25922, Pseudomonas aeruginosa ATCC 27583) using the microdilution method. The results obtained show that the metal complexes exhibit higher biological activity than the free ligands, confirming a synergistic effect. Further benzimidazolyl-phenol derivatives were explored for the detection of bacteria using fluorescence imaging studies. Interestingly, the fluorescent properties of these compounds make them potential candidates to monitor the morphology of bacteria at different compound concentrations. Hence, the interaction of the ligand and complexes with model membranes mimicking those of bacteria was studied by using differential scanning calorimetry (DSC) and molecular dynamics (MD), showing that both compounds decreased the enthalpy of transition in two model membranes as the concentration of the compounds increased. In addition, the main transition temperature was slightly reduced as a result of these interactions.

Dataset Information

Three New Metal Complexes with Imidazole-Containing Tripodal Ligands as Fluorophores for Nitroaromatics- and Ion-Selective Sensing.

Publications

Three New Metal Complexes with Imidazole-Containing Tripodal Ligands as Fluorophores for Nitroaromatics- and Ion-Selective Sensing.

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