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Open AccessArticle

Mono-, Bis-, and Tris-Chelate Zn(II) Complexes with Imidazo[1,5-a]pyridine: Luminescence and Structural Dependence

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Molecules 2023, 28(9), 3703; https://doi.org/10.3390/molecules28093703 - 25 Apr 2023

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Abstract

New mono-, bis-, and tris-chelate Zn(II) complexes have been synthesized starting from different Zn(II) salts and employing a fluorescent 1,3-substituted-imidazo[1,5-a]pyridine as a chelating ligand. The products have been characterized by single-crystal X-ray diffraction; mass spectrometry; and vibrational spectroscopy. The optical properties [...] Read more.

New mono-, bis-, and tris-chelate Zn(II) complexes have been synthesized starting from different Zn(II) salts and employing a fluorescent 1,3-substituted-imidazo[1,5-a]pyridine as a chelating ligand. The products have been characterized by single-crystal X-ray diffraction; mass spectrometry; and vibrational spectroscopy. The optical properties have been investigated to compare the performances of mono-, bis-, and tris-chelate forms. The collected data (in the solid state and in solution) elucidate an important modification of the ligand conformation upon metal coordination; which is responsible for a notable increase in the optical performance. An intense modification of the emission quantum yield along the series in the solid state is observed comparing mono-, bis-, and tris-chelate adducts; independently from the anionic ligand introduced by ionic exchange. Full article

(This article belongs to the Special Issue Synthesis and Applications of Transition Metal Complexes)

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Open AccessArticle

Effect of Metal Complexing on Mn–Fe/TS-1 Catalysts for Selective Catalytic Reduction of NO with NH₃

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Molecules 2023, 28(7), 3068; https://doi.org/10.3390/molecules28073068 - 29 Mar 2023

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Abstract

TS-1 zeolite with desirable pore structure, an abundance of acidic sites, and good thermal stability promising as a support for the selective catalytic reduction of NO with NH₃ (NH₃-SCR). Herein, a series of Mn–Fe/TS-1 catalysts have been synthesized, adopting tetraethylenepentamine [...] Read more.

TS-1 zeolite with desirable pore structure, an abundance of acidic sites, and good thermal stability promising as a support for the selective catalytic reduction of NO with NH₃ (NH₃-SCR). Herein, a series of Mn–Fe/TS-1 catalysts have been synthesized, adopting tetraethylenepentamine (TEPA) as a metal complexing agent using the one-pot hydrothermal method. The introduced TEPA can not only increase the loading of active components but also prompts the formation of a hierarchical structure through decreasing the size of TS-1 nanocrystals to produce intercrystalline mesopores during the hydrothermal crystallization process. The optimized Mn–Fe/TS-1(R-2) catalyst shows remarkable NH₃-SCR performance. Moreover, it exhibits excellent resistance to H₂O and SO₂ at low temperatures. The characterization results indicate that Mn–Fe/TS-1(R-2) possesses abundant surface Mn⁴⁺ and Fe²⁺ and chemisorbed oxygen, strong reducibility, and a high Brønsted acid amount. For comparison, Mn–Fe/TiO₂ displays a narrower active temperature window due to its poor thermostability. Full article

(This article belongs to the Special Issue Synthesis and Applications of Transition Metal Complexes)

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Open AccessArticle

Urea Decomposition Mechanism by Dinuclear Nickel Complexes

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Christian O. Martins

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Leticia K. Sebastiany

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Alejandro Lopez-Castillo

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Rafael S. Freitas

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Leandro H. Andrade

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Henrique E. Toma

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Caterina G. C. Marques Netto

Molecules 2023, 28(4), 1659; https://doi.org/10.3390/molecules28041659 - 09 Feb 2023

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Abstract

Urease is an enzyme containing a dinuclear nickel active center responsible for the hydrolysis of urea into carbon dioxide and ammonia. Interestingly, inorganic models of urease are unable to mimic its mechanism despite their similarities to the enzyme active site. The reason behind [...] Read more.

Urease is an enzyme containing a dinuclear nickel active center responsible for the hydrolysis of urea into carbon dioxide and ammonia. Interestingly, inorganic models of urease are unable to mimic its mechanism despite their similarities to the enzyme active site. The reason behind the discrepancy in urea decomposition mechanisms between inorganic models and urease is still unknown. To evaluate this factor, we synthesized two bis-nickel complexes, [Ni₂L(OAc)] (1) and [Ni₂L(Cl)(Et₃N)₂] (2), based on the Trost bis-Pro-Phenol ligand (L) and encompassing different ligand labilities with coordination geometries similar to the active site of jack bean urease. Both mimetic complexes produced ammonia from urea, (1) and (2), were ten- and four-fold slower than urease, respectively. The presence and importance of several reaction intermediates were evaluated both experimentally and theoretically, indicating the aquo intermediate as a key intermediate, coordinating urea in an outer-sphere manner. Both complexes produced isocyanate, revealing an activated water molecule acting as a base. In addition, the reaction with different substrates indicated the biomimetic complexes were able to hydrolyze isocyanate. Thus, our results indicate that the formation of an outer-sphere complex in the urease analogues might be the reason urease performs a different mechanism. Full article

(This article belongs to the Special Issue Synthesis and Applications of Transition Metal Complexes)

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Open AccessArticle

Ruthenium(II) Complexes Coupled by Erianin via a Flexible Carbon Chain as a Potential Stabilizer of c-myc G-Quadruplex DNA

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Molecules 2023, 28(4), 1529; https://doi.org/10.3390/molecules28041529 - 04 Feb 2023

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Abstract

Herein, two novel ruthenium(II) complexes coupled by erianin via a flexible carbon chain, [Ru(phen)₂(L₁-(CH₂)₄-erianin)](ClO₄)₂ (L₁ = 2-(2-(tri-fluoromethyphenyl))-imidazo [4,5f][1–10]phenanthroline (1) and [Ru(phen)₂(L₂-(CH₂)₄-eria)](ClO [...] Read more.

Herein, two novel ruthenium(II) complexes coupled by erianin via a flexible carbon chain, [Ru(phen)₂(L₁-(CH₂)₄-erianin)](ClO₄)₂ (L₁ = 2-(2-(tri-fluoromethyphenyl))-imidazo [4,5f][1–10]phenanthroline (1) and [Ru(phen)₂(L₂-(CH₂)₄-eria)](ClO₄)₂ (L₂ = 2-(4-(tri-fluoromethyphenyl))-imidazo [4,5f][1,10]phenanthroline (2), have been synthesized and investigated as a potential G-quadruplex(G4) DNA stabilizer. Both complexes, especially 2, can bind to c-myc G4 DNA with high affinity by electronic spectra, and the binding constant calculated for 1 and 2 is about 15.1 and 2.05 × 10⁷ M⁻¹, respectively. This was further confirmed by the increase in fluorescence intensity for both complexes. Moreover, the positive band at 265 nm in the CD spectra of c-myc G4 DNA decreased treated with 2, indicating that 2 may bind to c-myc G4 DNA through extern groove binding mode. Furthermore, fluorescence resonance energy transfer (FRET) assay indicated that the melting point of c-myc G4 DNA treated with 1 and 2 increased 15.5 and 16.5 °C, respectively. Finally, molecular docking showed that 1 can bind to c-myc G4 DNA in the extern groove formed by base pairs G7–G9 and G22–A24, and 2 inserts into the small groove of c-myc G4 DNA formed by base pairs T19–A24. In summary, these ruthenium(II) complexes, especially 2, can be developed as potential c-myc G4 DNA stabilizers and will be exploited as potential anticancer agents in the future. Full article

(This article belongs to the Special Issue Synthesis and Applications of Transition Metal Complexes)

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Studies on the Complexation of Platinum(II) by Some 4-Nitroisoxazoles and Testing the Cytotoxic Activity of the Resulting Complexes

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Molecules 2023, 28(3), 1284; https://doi.org/10.3390/molecules28031284 - 28 Jan 2023

Viewed by 637

Abstract

Two novel platinum(II) complexes (1 and 2) were synthesized by the reaction of the appropriate 3,5-dimethyl-4-nitroisoxazole with K₂PtCl₄ and characterized by elemental analysis, ESI MS spectrometry, ¹H NMR and far-IR spectroscopy. The structure of trans complex 2 [...] Read more.

Two novel platinum(II) complexes (1 and 2) were synthesized by the reaction of the appropriate 3,5-dimethyl-4-nitroisoxazole with K₂PtCl₄ and characterized by elemental analysis, ESI MS spectrometry, ¹H NMR and far-IR spectroscopy. The structure of trans complex 2 was additionally confirmed by X-ray diffraction. The cytotoxicity of the investigated compounds was examined in vitro on three human cancer cell lines (MCF-7 breast, ES-2 ovarian and A-549 lung adenocarcinomas) in both normoxia and hypoxia conditions. LogPs of complexes were measured using the shake-flask method. The trans complex 2 showed much better cytotoxic activity than cisplatin for all the tested cancer cell lines. Cis complex 1 was inferior to its trans isomer against all the cancer lines tested in normoxia conditions but proved superior to the reference cisplatin against the MCF-7 and A549 lines, and showed similar activity to cisplatin against the ES-2 line. To gain additional information that may facilitate the explanation of the pharmacological activity of the tested compounds, cellular platinum uptake and stability in L-glutathione solution were determined for both compounds 1 and 2. Full article

(This article belongs to the Special Issue Synthesis and Applications of Transition Metal Complexes)

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Open AccessArticle

Exploring the Co-Crystallization of Kojic Acid with Silver(I), Copper(II), Zinc(II), and Gallium(III) for Potential Antibacterial Applications

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Molecules 2023, 28(3), 1244; https://doi.org/10.3390/molecules28031244 - 27 Jan 2023

Cited by 1 | Viewed by 773

Abstract

Co-crystallization of kojic acid (HKA) with silver(I), copper(II), zinc(II), or gallium(III) salts yielded three 1D coordination polymers and one 0D complex in which kojic acid was present as a neutral or anionic terminal or bridging ligand. All reactions were conducted mechanochemically via ball [...] Read more.

Co-crystallization of kojic acid (HKA) with silver(I), copper(II), zinc(II), or gallium(III) salts yielded three 1D coordination polymers and one 0D complex in which kojic acid was present as a neutral or anionic terminal or bridging ligand. All reactions were conducted mechanochemically via ball milling and manual grinding, or via slurry. All solids were fully characterized via single-crystal and/or powder X-ray diffraction. As kojic acid is a mild antimicrobial compound that is widely used in cosmetics, and the metal cations possess antibacterial properties, their combinations were tested for potential antibacterial applications. The minimal inhibition concentrations (MICs) and minimal biocidal concentrations (MBCs) for all compounds were measured against standard strains of the bacteria P. aeruginosa, S. aureus, and E. coli. All compounds exerted appreciable antimicrobial activity in the order of silver, zinc, copper, and gallium complexes. Full article

(This article belongs to the Special Issue Synthesis and Applications of Transition Metal Complexes)

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Open AccessArticle

Remote Steric Control of the Tetrahedral Coordination Geometry around Heteroleptic Copper(I) Bis(Diimine) Complexes

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Jordan L. Appleton

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Christophe Gourlaouen

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Romain Ruppert

Molecules 2023, 28(3), 983; https://doi.org/10.3390/molecules28030983 - 18 Jan 2023

Viewed by 1040

Abstract

In this study, a series of new heteroleptic copper(I) bis(diimine) complexes are described. Using one highly hindered phenanthroline ligand and a second less-hindered diimine ligand led to unexpected results. Following a two-step one-pot method to obtain heteroleptic copper(I) complexes, an almost perfect tetrahedral [...] Read more.

In this study, a series of new heteroleptic copper(I) bis(diimine) complexes are described. Using one highly hindered phenanthroline ligand and a second less-hindered diimine ligand led to unexpected results. Following a two-step one-pot method to obtain heteroleptic copper(I) complexes, an almost perfect tetrahedral coordination geometry around the copper(I) ion was obtained in several cases, despite the fact that at least one ligand was not sterically encumbered near the coordination site (at the position α to the nitrogen atoms of the ligand). This was demonstrated in the solid state by resolution of crystal structures, and these findings, corroborated by calculations, showed that the non-covalent interactions between the two diimine ligands present in these complexes were governing these structural features. The electronic properties of all complexes were also determined and the fluorescence lifetimes of two complexes were compared. Full article

(This article belongs to the Special Issue Synthesis and Applications of Transition Metal Complexes)

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Open AccessArticle

N-Heterocyclic Carbene-Iridium Complexes as Photosensitizers for In Vitro Photodynamic Therapy to Trigger Non-Apoptotic Cell Death in Cancer Cells

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Molecules 2023, 28(2), 691; https://doi.org/10.3390/molecules28020691 - 10 Jan 2023

Cited by 1 | Viewed by 1362

Abstract

A series of seven novel iridium complexes were synthetized and characterized as potential photosensitizers for photodynamic therapy (PDT) applications. Among them, four complexes were evaluated in vitro for their anti-proliferative activity with and without irradiation on a panel of five cancer cell lines, [...] Read more.

A series of seven novel iridium complexes were synthetized and characterized as potential photosensitizers for photodynamic therapy (PDT) applications. Among them, four complexes were evaluated in vitro for their anti-proliferative activity with and without irradiation on a panel of five cancer cell lines, namely PC-3 (prostate cancer), T24 (bladder cancer), MCF7 (breast cancer), A549 (lung cancer) and HeLa (cervix cancer), and two non-cancerous cell models (NIH-3T3 fibroblasts and MC3T3 osteoblasts). After irradiation at 458 nm, all tested complexes showed a strong selectivity against cancer cells, with a selectivity index (SI) ranging from 8 to 34 compared with non-cancerous cells. The cytotoxic effect of all these complexes was found to be independent of the anti-apoptotic protein Bcl-xL. The compound exhibiting the best selectivity, complex 4a, was selected for further investigations. Complex 4a was mainly localized in the mitochondria. We found that the loss of cell viability and the decrease in ATP and GSH content induced by complex 4a were independent of both Bcl-xL and caspase activation, leading to a non-apoptotic cell death. By counteracting the intrinsic or acquired resistance to apoptosis associated with cancer, complex 4a could be an interesting therapeutic alternative to be studied in preclinical models. Full article

(This article belongs to the Special Issue Synthesis and Applications of Transition Metal Complexes)

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Open AccessArticle

Rhenium(I) Block Copolymers Based on Polyvinylpyrrolidone: A Successful Strategy to Water-Solubility and Biocompatibility

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Kristina S. Kisel

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Vadim A. Baigildin

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Anastasia I. Solomatina

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Molecules 2023, 28(1), 348; https://doi.org/10.3390/molecules28010348 - 01 Jan 2023

Viewed by 906

Abstract

A series of diphosphine Re(I) complexes Re1–Re4 have been designed via decoration of the archetypal core {Re(CO)₂(N^N)} through the installations of the phosphines P⁰ and P¹ bearing the terminal double bond, where N^N = 2,2′-bipyridine (N^N1 [...] Read more.

A series of diphosphine Re(I) complexes Re1–Re4 have been designed via decoration of the archetypal core {Re(CO)₂(N^N)} through the installations of the phosphines P⁰ and P¹ bearing the terminal double bond, where N^N = 2,2′-bipyridine (N^N1), 4,4′-di-tert-butyl-2,2′-bipyridine (N^N2) or 2,9-dimethyl-1,10-phenanthroline (N^N3) and P⁰ = diphenylvinylphosphine, and P¹ = 4-(diphenylphosphino)styrene. These complexes were copolymerized with the corresponding N-vinylpyrrolidone-based Macro-RAFT agents of different polymer chain lengths to give water-soluble copolymers of low-molecular p(VP-l-Re) and high-molecular p(VP-h-Re) block-copolymers containing rhenium complexes. Compounds Re1–Re4, as well as the copolymers p(VP-l-Re) and p(VP-h-Re), demonstrate phosphorescence from a ³MLCT excited state typical for this type of chromophores. The copolymers p(VP-l-Re#) and p(VP-h-Re#) display weak sensitivity to molecular oxygen in aqueous and buffered media, which becomes almost negligible in the model physiological media. In cell experiments with CHO-K1 cell line, p(VP-l-Re2) and p(VP-h-Re2) displayed significantly reduced toxicity compared to the initial Re2 complex and internalized into cells presumably by endocytic pathways, being eventually accumulated in endosomes. The sensitivity of the copolymers to oxygen examined in CHO-K1 cells via phosphorescence lifetime imaging microscopy (PLIM) proved to be inessential. Full article

(This article belongs to the Special Issue Synthesis and Applications of Transition Metal Complexes)

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Open AccessArticle

Synthesis and Characterization of Late Transition Metal Complexes of Mono-Acetate Pendant Armed Ethylene Cross-Bridged Tetraazamacrocycles with Promise as Oxidation Catalysts for Dye Bleaching

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Molecules 2023, 28(1), 232; https://doi.org/10.3390/molecules28010232 - 27 Dec 2022

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Abstract

Ethylene cross-bridged tetraazamacrocycles are known to produce kinetically stable transition metal complexes that can act as robust oxidation catalysts under harsh aqueous conditions. We have synthesized ligand analogs with single acetate pendant arms that act as pentadentate ligands to Mn, Fe, Co, Ni, [...] Read more.

Ethylene cross-bridged tetraazamacrocycles are known to produce kinetically stable transition metal complexes that can act as robust oxidation catalysts under harsh aqueous conditions. We have synthesized ligand analogs with single acetate pendant arms that act as pentadentate ligands to Mn, Fe, Co, Ni, Cu, and Zn. These complexes have been synthesized and characterized, including the structural characterization of four Co and Cu complexes. Cyclic voltammetry demonstrates that multiple oxidation states are stabilized by these rigid, bicyclic ligands. Yet, redox potentials of the metal complexes are modified compared to the “parent” ligands due to the pendant acetate arm. Similarly, gains in kinetic stability under harsh acidic conditions, compared to parent complexes without the pendant acetate arm, were demonstrated by a half-life seven times longer for the cyclam copper complex. Due to the reversible, high oxidation states available for the Mn and Fe complexes, the Mn and Fe complexes were examined as catalysts for the bleaching of three commonly used pollutant model dyes (methylene blue, methyl orange, and Rhodamine B) in water with hydrogen peroxide as oxidant. The efficient bleaching of these dyes was observed. Full article

(This article belongs to the Special Issue Synthesis and Applications of Transition Metal Complexes)

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Coordination Polymers Based on Rhenium Octahedral Chalcocyanide Cluster Anions and Ag⁺ Cations with Bipyridine Analogs

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Molecules 2022, 27(22), 7684; https://doi.org/10.3390/molecules27227684 - 09 Nov 2022

Cited by 1 | Viewed by 845

Abstract

A series of six coordination polymers based on octahedral cluster anions [Re₆Q₈(CN)₆]⁴⁻ (Q = S or Se) and Ag⁺ cations coordinated by bipyridine analogs were synthesized under solvothermal conditions. Their structures have been characterized by [...] Read more.

A series of six coordination polymers based on octahedral cluster anions [Re₆Q₈(CN)₆]⁴⁻ (Q = S or Se) and Ag⁺ cations coordinated by bipyridine analogs were synthesized under solvothermal conditions. Their structures have been characterized by single crystal X-ray diffraction. Compounds 1 and 2 described by the general formula [{Ag(phen)}₄Re₆Q₈(CN)₆] (Q = Se (1), S (2); phen = 1,10-phenanthroline) exhibit layered structures assembled into a supramolecular network by CH…π contacts. At the same time, compounds [{Ag(bipym)}₂Ag₂Re₆Se₈(CN)₆] (bipym = 2,2′-bipyrimidine) (3), [{Ag₂(bipy)}Ag₂Re₆Se₈(CN)₆]·CH₃CN (bipy = 4,4′-bipyridine) (4) and [{Ag(dpbp)}₄Re₆Q₈(CN)₆]·2H₂O·2CH₃CN (Q = Se (5), S (6); dpbp = 4,4′-Di(4-pyridyl)biphenyl)) evince framework structures. In 1, 2, 5 and 6 weak Ag⋯Ag interactions are observed. All the compounds show luminescence in the red region. The luminescence quantum yields and lifetimes were found to be notably higher than those for most of the coordination polymers based on the octahedral rhenium cluster complexes. Full article

(This article belongs to the Special Issue Synthesis and Applications of Transition Metal Complexes)

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Reactions of a Dioxidomolybdenum(VI) Complex with Thionation Reagents—Formation of Mo(IV) Species with Sulfur Donors

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Molecules 2022, 27(21), 7154; https://doi.org/10.3390/molecules27217154 - 22 Oct 2022

Viewed by 593

Abstract

Molecular molybdenum complexes with sulfur donor ligands are generally studied as soluble model compounds for molybdenum enzymes essential for life. The dioxidomolybdenum(VI) complex with tetradentate aminobisphenolate ligand undergoes a reaction with thionation reagent P₂S₅ or its organic derivative, Lawesson’s reagent, [...] Read more.

Molecular molybdenum complexes with sulfur donor ligands are generally studied as soluble model compounds for molybdenum enzymes essential for life. The dioxidomolybdenum(VI) complex with tetradentate aminobisphenolate ligand undergoes a reaction with thionation reagent P₂S₅ or its organic derivative, Lawesson’s reagent, to yield stable Mo(IV) aminobisphenolate complexes, where pristine oxido ligands have been replaced by bidentate sulfur donors tetrasulfide, S₄²⁻ or (4-methoxyphenyl)phosphonotrithioate residue derived from Lawesson’s reagent. This is in contrast to the behaviour of analogous dioxidotungsten(VI) complex, which, under similar conditions, yields W(VI) S₂ systems. The overall cis,trans,cis geometry of the parent dioxidomolybdenum(VI) aminobisphenolate is retained, namely, the neutral nitrogen donors are in cis positions, phenolate oxygens are trans to each other and sulfur donors are cis. Although formally Mo(IV), thus d² system, the studied complexes have diamagnetic singlet electron configurations as a result of the axially compressed octahedral structures. Full article

(This article belongs to the Special Issue Synthesis and Applications of Transition Metal Complexes)

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Open AccessArticle

Synthesis and Application of New Salan Titanium Complexes in the Catalytic Reduction of Aldehydes

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Joana Hipólito

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Ana M. Martins

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Luis G. Alves

Molecules 2022, 27(20), 6821; https://doi.org/10.3390/molecules27206821 - 12 Oct 2022

Cited by 1 | Viewed by 709

Abstract

Complexes of formula [(H₂N₂O₂)TiCl₂] and [(H₂N₂O₂)Ti(OⁱPr)₂] (H₂N₂O₂H₂ = HOPh’CH₂NH(CH₂)₂NHCH₂Ph’OH, where [...] Read more.

Complexes of formula [(H₂N₂O₂)TiCl₂] and [(H₂N₂O₂)Ti(OⁱPr)₂] (H₂N₂O₂H₂ = HOPh’CH₂NH(CH₂)₂NHCH₂Ph’OH, where Ph’ = 2,4-(CMe₂Ph)C₆H₂) were synthesized by the reaction of the salan ligand precursor H₂N₂O₂H₂ with TiCl₄ and Ti(OⁱPr)₄, respectively, in high yields. The dichlorido complex [(H₂N₂O₂)TiCl₂] revealed to be an efficient catalyst for the reduction of benzaldehyde in toluene. Full conversion was observed after 24 h at 55 °C in THF. The same catalyst also converted phenylacetaldehyde and hydrocinnamaldehyde into the corresponding alkanes quantitatively. Full article

(This article belongs to the Special Issue Synthesis and Applications of Transition Metal Complexes)

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Iron(II) Mediated Supramolecular Architectures with Schiff Bases and Their Spin-Crossover Properties

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Nandakumar Kalarikkal

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Madhu Thomas

Molecules 2023, 28(3), 1012; https://doi.org/10.3390/molecules28031012 - 19 Jan 2023

Viewed by 1018

Abstract

Supramolecular architectures, which are formed through the combination of inorganic metal cations and organic ligands by self-assembly, are one of the techniques in modern chemical science. This kind of multi-nuclear system in various dimensionalities can be implemented in various applications such as sensing, [...] Read more.

Supramolecular architectures, which are formed through the combination of inorganic metal cations and organic ligands by self-assembly, are one of the techniques in modern chemical science. This kind of multi-nuclear system in various dimensionalities can be implemented in various applications such as sensing, storage/cargo, display and molecular switching. Iron(II) mediated spin-crossover (SCO) supramolecular architectures with Schiff bases have attracted the attention of many investigators due to their structural novelty as well as their potential application possibilities. In this paper, we review a number of supramolecular SCO architectures of iron(II) with Schiff base ligands exhibiting varying geometrical possibilities. The structural and SCO behavior of these complexes are also discussed in detail. Full article

(This article belongs to the Special Issue Synthesis and Applications of Transition Metal Complexes)

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