Copper(I) complexes of 2-methoxy-(5-trifluoromethyl-phenyl)-pyridine-2yl-methylene-amine: Impact of phosphine ancillary ligands on luminescence and catalytic properties of the copper(I) complexes

Chavan, S.S.; Sawant, S.K.; Pawal, S.B.; More, M.S.

doi:10.1016/j.poly.2015.11.050

Cited by 18 publications

(2 citation statements)

References 32 publications

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“…A similar shift was also seen in the signals of ν(C−O) between the ligands and complexes, indicating the coordination of phenol oxygen to the copper. These observations were consistent with other published works involving copper complexes [ 19 , 23 , 24 , 25 , 26 ]. The signals observed around 460 and 410 cm −1 in the spectra were assigned to the stretching frequencies of the copper-donor atom-chelating ligand, ν(Cu−O) and ν(Cu−N), respectively.…”

Section: Resultssupporting

confidence: 94%

Efficient Catalytic Reduction of 4-Nitrophenol Using Copper(II) Complexes with N,O-Chelating Schiff Base Ligands

et al. 2021

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The reduction of 4-nitrophenol to 4-aminophenol by sodium borohydride was used as a model to test the catalytic activity of copper(II) complexes containing N,O-chelating Schiff base ligands. In this study, a series of copper(II) complexes containing respective Schiff base ligands, N′-salicylidene-2-aminophenol (1), N′-salicylidene-2-aminothiazole (2), and N,N′-bis(salicylidene)-o-phenylenediamine (3), were synthesized and characterized by elemental analysis, Fourier transform infrared (FT-IR), and UV-Visible (UV-Vis) and electron paramagnetic resonance (EPR) spectroscopies. The results from the 4-nitrophenol reduction showed that 3 has the highest catalytic activities with 97.5% conversion, followed by 2 and 1 with 95.2% and 90.8% conversions, respectively. The optimization of the catalyst amount revealed that 1.0 mol% of the catalyst was the most optimized amount with the highest conversion compared to the other doses, 0.5 mol% and 1.5 mol%. Recyclability and reproducibility tests confirmed that all three complexes were active, efficient, and possess excellent reproducibility with consistent catalytic performances and could be used again without a major decrease in the catalytic activity.

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Section: Resultssupporting

confidence: 94%

Efficient Catalytic Reduction of 4-Nitrophenol Using Copper(II) Complexes with N,O-Chelating Schiff Base Ligands

et al. 2021

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“…In solution, the complexes are likely to be unstable upon oxidation, as indicated by an irreversible wave. [ 56–59 ]…”

Section: Resultsmentioning

confidence: 99%

Synthesis, structure, characterization and biological evaluation of 3‐substituted 1‐pyridin‐2‐ylimidazo[1,5‐a]pyridine‐based copper(I)–phosphine complexes for anticancer drug screening

Pathaw

Khamrang

Selvakumaran

et al. 2020

Applied Organom Chemis

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Copper(I) complexes of the types [Cu(N-N)(PPh 3) 2 ]NO 3 (LC41-LC44) and [Cu(N-N)(PPh 3)(NO 3)] (LC45) carrying 3-substituted 1-pyridine-2-ylimidazo[1,5-a]pyridine (N-N) derivatives and triphenylphosphine (PPh 3) ligands have been prepared. The synthesized copper(I)-phosphine complexes were fully characterized by NMR, IR, ESI-MS and UV-visible spectroscopy as well as by cyclic voltammetry. Selected structures such as LC42, LC43 and LC45 were additionally analysed by single-crystal X-ray method, which show that copper(I) centre adopts a highly distorted tetrahedral geometry. The 1 H and 13 C NMR spectral data of the complexes throw light on the nature of metal-ligand bonding. They display dπ-π* metal-to-ligand charge transfer (MLCT) transition and show quasireversible Cu I /Cu II metal oxidation. Among the copper(I)-phosphine complexes, LC41-LC44 exhibit moderate cytotoxicity (IC 50 : 24 h, 67-74 μM; 48 h, 58-70 μM) against human lung epithelial adenocarcinoma A549 cells, whereas LC45 displays the best activity (IC 50 : 24 h, 42 μM; 48 h, 34 μM) for A549 cancer cell line, which is better than that of the commercial antitumor drug cisplatin. All the complexes also displayed excellent selectivity by being relatively inactive against the human lung epithelial L132 normal cell line with selectivity index (SI) values ranging from 3.4 to 7.4. The complexes block cell cycle progression of A549 cells in G 0 /G 1 phase. FACSVerse analyses are suggestive of reactive oxygen species (ROS) generation and apoptotic cell death induced by the LC41, LC43 and LC45. The induction of apoptosis in A549 cells was shown by Annexin V with propidium iodide (PI) and 4 0 ,6-diamidino-2-phenylindole (DAPI) staining methods and established the ability of LC41, LC43 and LC45 to accumulate in the cell nuclei. Larica Pathaw and Themmila Khamrang contributed equally to this work.

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Copper(I) Complexes of N-(2-{[(2E)-2-(4-Nitrobenzylidenyl)Hydrazinyl]Carbonyl}Phenyl)Benzamide and Triphenylphosphine: Synthesis, Characterization and Luminescence Properties

Chavan

Pawal

et al. 2016

J Fluoresc

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Copper(I) complexes of the formula [Cu(L)(PPh)]X (1-4) (X = Cl(1), ClO(2), BF(3) and PF(4)) [where L = N-(2-{[(2E)-2-(4-nitrobenzylidenyl)hydrazinyl]carbonyl}phenyl)benzamide; PPh = triphenylphosphine] have been prepared by the condensation of N-[2-(hydrazinocarbonyl)phenyl]benzamide with 4-nitrobenzaldehyde followed by the reaction with CuCl, [Cu(MeCN)]ClO, [Cu(MeCN)]BF and [Cu(MeCN)]PF in presence of triphenylphosphine as a coligand. Complexes 1-4 were then characterized by elemental analyses, FTIR, UV-visible and H NMR spectroscopy. Mononuclear copper(I) complexes 1-4 were formed with L in its keto form by involvement of azomethine nitrogen and the carbonyl oxygen along with two PPh groups. A single crystal X-ray diffraction study of the representative complex [(Cu(L)(PPh)]CIO (2) reveals a distorted tetrahedral geometry around Cu(I). Crystal data of (2): space group = C2/c, a = 42.8596 (9) Å, b = 14.6207 (3) Å, c = 36.4643 (7) Å, V = 20,653.7 (7) Å, Z = 16. Complexes 1-4 exhibit quasireversible redox behaviour corresponding to a Cu(I)/Cu(II) couple. All complexes show blue-green emission as a result of fluorescence from an intra-ligand charge transition (ILCT), ligand to ligand charge transfer transition (LLCT) or mixture of both. Significant increase in size of the counter anion shows marked effect on quantum efficiency and lifetime of the complexes in solution.

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Copper(I) complexes of 2-methoxy-(5-trifluoromethyl-phenyl)-pyridine-2yl-methylene-amine: Impact of phosphine ancillary ligands on luminescence and catalytic properties of the copper(I) complexes

Cited by 18 publications

References 32 publications

Efficient Catalytic Reduction of 4-Nitrophenol Using Copper(II) Complexes with N,O-Chelating Schiff Base Ligands

Efficient Catalytic Reduction of 4-Nitrophenol Using Copper(II) Complexes with N,O-Chelating Schiff Base Ligands

Synthesis, structure, characterization and biological evaluation of 3‐substituted 1‐pyridin‐2‐ylimidazo[1,5‐a]pyridine‐based copper(I)–phosphine complexes for anticancer drug screening

Copper(I) Complexes of N-(2-{[(2E)-2-(4-Nitrobenzylidenyl)Hydrazinyl]Carbonyl}Phenyl)Benzamide and Triphenylphosphine: Synthesis, Characterization and Luminescence Properties

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