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Recent Advance in Transition Metal Complexes and Their Applications

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A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Applied Chemistry".

Deadline for manuscript submissions: closed (30 September 2023) | Viewed by 23205

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Dr. Yungen Liu

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Guest Editor

Department of Chemistry, Southern University of Science and Technology, Shenzhen 518055, China
Interests: C-H bond functionalization; non-precious transition metals; organic synthesis; catalysis; iron; nitrenoids; amination; oxidation
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Special Issue Information

Dear Colleagues,

Transition-metal complexes are widely applied in various transformation reactions and crucial in synthetic organic chemistry, especially for the preparation of complex natural molecules, pharmaceuticals and fine chemicals. Traditionally, these metal complexes heavily depend on the second- and third-row transition metals, such as palladium, rhodium and iridium. With the pressing need for green and sustainable synthetic processes, there has been a shift towards investigating catalytic reactions involving the use of first-row transition-metal catalysts , which are more abundant and less toxic compared to their second- and third-row counterparts.

This Special Issue presents the latest research on transition-metal complexes and their applications, including characterization and property studies on structurally interesting metal complexes, applications of metal complexes in various transformation reactions and mechanistic studies.

Dr. Yungen Liu
Guest Editor

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Keywords

transition metals
applications
organic synthesis
atom/group transfer
C-H bond activation/functionalization
pharmaceuticals and natural products

Related Special Issue

Recent Advance in Transition Metal Complexes and Their Applications II in Molecules (1 article)

Published Papers (13 papers)

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Research

22 pages, 6435 KiB

Open AccessArticle

Stereochemical Properties of Two Schiff-Base Transition Metal Complexes and Their Ligand by Using Multiple Chiroptical Spectroscopic Tools and DFT Calculations

by Guojie Li, Dan Li, Mutasem Alshalalfeh, Joseph Cheramy, Hui Zhang and Yunjie Xu

Molecules 2023, 28(6), 2571; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules28062571 - 12 Mar 2023

Cited by 5 | Viewed by 1677

Abstract

Two transition metal complexes were synthesized with Ni(II) and Cu(II) using a tetradentate Schiff-base ligand, (R,R) and (S,S)-N,N′-Bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine. The stereochemical properties of the ligand and the metal complexes were investigated using a combined experimental and theoretical approach. Multiple spectroscopic techniques, which include IR, vibrational circular dichroism (VCD), UV-Vis and electronic circular dichroism (ECD), as well as Raman and the newly discovered ECD-circularly polarized Raman (i.e., eCP-Raman) spectroscopies were utilized. The good agreement achieved between the experimental and simulated IR, VCD, UV-Vis and ECD spectra of the ligand allowed one to identify the presence of three main ligand conformers in solution, thanks, especially to the high VCD sensitivity to the conformations associated with the tertbutyl groups. The helicity of the metal complexes was identified to be M and P for those with the (R,R) and (S,S) ligands, respectively. Furthermore, eCP-Raman measurements were carried out for the two metal complexes under (near) resonance. Their induced solvent chiral Raman features were explained, and the potential application of eCP-Raman was discussed. Full article

(This article belongs to the Special Issue Recent Advance in Transition Metal Complexes and Their Applications)

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12 pages, 2871 KiB

Open AccessArticle

Ln(III) Complexes Embedded in Biocompatible PLGA Nanoparticles as Potential Vis-to-NIR Optical Probes

by Fabio Piccinelli, Silvia Mizzoni, Giorgia Zanella, Salvatore Calogero Gaglio, Massimiliano Perduca, Alessandro Romeo, Silvia Ruggieri, Chiara Nardon and Enrico Cavalli

Molecules 2023, 28(5), 2251; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules28052251 - 28 Feb 2023

Cited by 1 | Viewed by 1426

Abstract

In this contribution, we present the spectroscopic study of two NIR emitting hydrophobic heteroleptic (R,R)-YbL1(tta) and (R,R)-NdL1(tta) complexes (with tta = 2-thenoyltrifluoroacetonate and L1 = N,N′-bis(2-(8-hydroxyquinolinate)methylidene)-1,2-(R,R or S,S)-cyclohexanediamine), both in methanol solution and embedded in water dispersible and biocompatible poly lactic-co-glycolic acid (PLGA) nanoparticles. Thanks to their absorption properties in a wide range of wavelengths extending from the UV up to the blue and green visible regions, the emission of these complexes can be effectively sensitized using visible radiation, which is much less harmful to tissues and skin than the UV one. The encapsulation of the two Ln(III)-based complexes in PLGA allows us to preserve their nature, making them stable in water and to test their cytotoxicity on two different cell lines, with the aim of using them in the future as potential bioimaging optical probes. Full article

(This article belongs to the Special Issue Recent Advance in Transition Metal Complexes and Their Applications)

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14 pages, 18571 KiB

Open AccessArticle

Structurally-New Hexadecanuclear Ni-Containing Silicotungstate with Catalytic Hydrogen Generation Activity

by Yequn Wang, Xing Xin, Yeqin Feng, Manzhou Chi, Ruijie Wang, Tianfu Liu and Hongjin Lv

Molecules 2023, 28(5), 2017; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules28052017 - 21 Feb 2023

Viewed by 1794

Abstract

A structurally-new, carbon-free hexadecanuclear Ni-containing silicotungstate, [Ni₁₆(H₂O)₁₅(OH)₉(PO₄)₄(SiW₉O₃₄)₃]^19-, has been facilely synthesized using a one-pot, solution-based synthetic method systematically characterized by single-crystal X-ray diffraction and several other techniques. The resulting complex works as a noble-metal-free catalyst for visible-light-driven catalytic generation of hydrogen, by coupling with a [Ir(coumarin)₂(dtbbpy)][PF₆] photosensitizer and a triethanolamine (TEOA) sacrificial electron donor. Under minimally optimized conditions, a turnover number (TON) of 842 was achieved for TBA-Ni₁₆P₄(SiW₉)₃-catalyzed hydrogen evolution system. The structural stability of TBA-Ni₁₆P₄(SiW₉)₃ catalyst under photocatalytic conditions was evaluated by the mercury-poisoning test, FT-IR, and DLS measurements. The photocatalytic mechanism was elucidated by both time-solved luminescence decay and static emission quenching measurements. Full article

(This article belongs to the Special Issue Recent Advance in Transition Metal Complexes and Their Applications)

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16 pages, 3569 KiB

Open AccessArticle

Slow Magnetic Relaxation and Modulated Photoluminescent Emission of Coordination Polymer Based on 3-Amino-4-hydroxybenzoate Zn and Co Metal Ions

by Estitxu Echenique-Errandonea, Sara Rojas, Javier Cepeda, Duane Choquesillo-Lazarte, Antonio Rodríguez-Diéguez and José M. Seco

Molecules 2023, 28(4), 1846; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules28041846 - 15 Feb 2023

Cited by 2 | Viewed by 1215

Abstract

As a starting point, a new 3D porous framework with the {[CoL]·0.5DMF·H₂O}_n chemical formula (where L = 3-amino-4-hydroxybenzoate) is described. Its performance as a single molecule magnet was explored. The study of magnetic properties reveals that Co-MOF shows no frequency-fdependant alternating current (ac) signals under zero direct current (dc) magnetic field, whereas single-molecule magnet behaviour is achieved when Co^II ions are diluted in a Zn^II based matrix. Interestingly, this strategy renders a bifunctional [Co_xZn_1-xL]_n material that is also characterized by a strong photoluminescent emitting capacity. Full article

(This article belongs to the Special Issue Recent Advance in Transition Metal Complexes and Their Applications)

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28 pages, 8328 KiB

Open AccessArticle

A Bridge too Far? Comparison of Transition Metal Complexes of Dibenzyltetraazamacrocycles with and without Ethylene Cross-Bridges: X-ray Crystal Structures, Kinetic Stability, and Electronic Properties

by Ashlie N. Walker, Megan A. Ayala, Somrita Mondal, Mackenzie C. Bergagnini, Phuong John D. Bui, Stephanie N. Chidester, Chad I. Doeden, Louise Esjornson, Brian R. Sweany, Leslie Garcia, Jeanette A. Krause, Allen G. Oliver, Timothy J. Prior and Timothy J. Hubin

Molecules 2023, 28(2), 895; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules28020895 - 16 Jan 2023

Cited by 1 | Viewed by 1835

Abstract

Tetraazamacrocycles, cyclic molecules with four nitrogen atoms, have long been known to produce highly stable transition metal complexes. Cross-bridging such molecules with two-carbon chains has been shown to enhance the stability of these complexes even further. This provides enough stability to use the resulting compounds in applications as diverse and demanding as aqueous, green oxidation catalysis all the way to drug molecules injected into humans. Although the stability of these compounds is believed to result from the increased rigidity and topological complexity imparted by the cross-bridge, there is insufficient experimental data to exclude other causes. In this study, standard organic and inorganic synthetic methods were used to produce unbridged dibenzyl tetraazamacrocycle complexes of Co, Ni, Cu, and Zn that are analogues of known cross-bridged tetraazamacrocycles and their transition metal complexes to allow direct comparison of molecules that are identical except for the cross-bridge. The syntheses of the known tetraazamacrocycles and the new transition metal complexes were successful with high yields and purity. Initial chemical characterization of the complexes was conducted by UV-Visible spectroscopy, while cyclic voltammetry showed more marked differences in electronic properties from bridged versions. Direct comparison studies of the unbridged and bridged compounds’ kinetic stabilities, as demonstrated by decomposition using high acid concentration and elevated temperature, showed that the cyclen-based complex stability did not benefit from cross-bridging. This is likely due to poor complementarity with the Cu²⁺ ion while cyclam-based complexes benefited greatly. We conclude that ligand–metal complementarity must be maintained in order for the topological and rigidity constraints imparted by the cross-bridge to contribute significantly to complex robustness. Full article

(This article belongs to the Special Issue Recent Advance in Transition Metal Complexes and Their Applications)

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10 pages, 1084 KiB

Open AccessArticle

Phosphine Oxide-Promoted Rh(I)-Catalyzed C–H Cyclization of Benzimidazoles with Alkenes

by Mingzhen Lu, Weiwei Xu and Mengchun Ye

Molecules 2023, 28(2), 736; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules28020736 - 11 Jan 2023

Viewed by 1507

Abstract

Ligands play a critical role in promoting transition-metal-catalyzed C–H activation reactions. However, owing to high sensitivity of the reactivity of C–H activation to metal catalysts, the development of effective ligands has been a formidable challenge in the field. Rh(I)-catalyzed C–H cyclization of benzimidazoles with alkenes has been faced with low reactivity, often requiring very harsh conditions. To address this challenge, a phosphine oxide-enabled Rh(I)–Al bimetallic catalyst was developed for the reaction, significantly promoting the reactivity and allowing the reaction to run at 120 °C with up to 97% yield. Full article

(This article belongs to the Special Issue Recent Advance in Transition Metal Complexes and Their Applications)

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14 pages, 3495 KiB

Open AccessArticle

Green Emissive Copper(I) Coordination Polymer Supported by the Diethylpyridylphosphine Ligand as a Luminescent Sensor for Overheating Processes

by Kamila R. Enikeeva, Aliia V. Shamsieva, Anna G. Strelnik, Robert R. Fayzullin, Dmitry V. Zakharychev, Ilya E. Kolesnikov, Irina R. Dayanova, Tatiana P. Gerasimova, Igor D. Strelnik, Elvira I. Musina, Andrey A. Karasik and Oleg G. Sinyashin

Molecules 2023, 28(2), 706; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules28020706 - 10 Jan 2023

Cited by 4 | Viewed by 1613

Abstract

Tertiary diethylpyridylphosphine was synthesized by the reaction of pyridylphosphine with bromoethane in a suberbasic medium. The reaction of phosphine with the copper(I) iodide led to the formation of a copper(I) coordination polymer, which, according to the X-ray diffraction data, has an intermediate structure with a copper-halide core between the octahedral and stairstep geometries of the Cu₄I₄ clusters. The obtained coordination polymer exhibits a green emission in the solid state, which is caused by the ³(M+X)LCT transitions. The heating up of the copper(I) coordination polymer to 138.5 °C results in its monomerization and the formation of a new solid-state phase. The new phase exhibits a red emission, with the emission band maximum at 725 nm. According to the experimental data and quantum chemical computations, it was concluded that depolymerization probably leads to a complex that is formed with the octahedral structure of the copper-halide core. The resulting solid-state phase can be backward-converted to the polymer phase via recrystallization from the acetone or DMF. Therefore, the obtained coordination polymer can be considered a sensor or detector for the overheating of processes that should be maintained at temperatures below 138 °C (e.g., engines, boiling liquids, solar heat systems, etc.). Full article

(This article belongs to the Special Issue Recent Advance in Transition Metal Complexes and Their Applications)

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10 pages, 8419 KiB

Open AccessArticle

Effect of 3d Transition Metal Atom Intercalation Concentration on the Electronic and Magnetic Properties of Graphene/MoS₂ Heterostructure: A First-Principles Study

by Feng Wu, Zijin Wang, Jiaqi He, Zhenzhe Li, Lijuan Meng and Xiuyun Zhang

Molecules 2023, 28(2), 509; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules28020509 - 4 Jan 2023

Cited by 1 | Viewed by 1525

Abstract

The electronic and magnetic properties of graphene/MoS₂ heterostructures intercalated with 3d transition metal (TM) atoms at different concentrations have been systematically investigated by first principles calculations. The results showed that all the studied systems are thermodynamically stable with large binding energies of about 3.72 eV–6.86 eV. Interestingly, all the TM-intercalated graphene/MoS₂ heterostructures are ferromagnetic and their total magnetic moments increase with TM concentration. Furthermore, TM concentration-dependent spin polarization is obtained for the graphene layer and MoS₂ layer due to the charge transfer between TM atoms and the layers. A significant band gap is opened for graphene in these TM-intercalated graphene/MoS₂ heterostructures (around 0.094 eV–0.37 eV). With the TM concentration increasing, the band gap of graphene is reduced due to the enhanced spin polarization of graphene. Our study suggests a research direction for the manipulation of the properties of 2D materials through control of the intercalation concentration of TM atoms. Full article

(This article belongs to the Special Issue Recent Advance in Transition Metal Complexes and Their Applications)

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12 pages, 2303 KiB

Open AccessArticle

Mechanism and Selectivity of Electrochemical Reduction of CO₂ on Metalloporphyrin Catalysts from DFT Studies

by Zaheer Masood and Qingfeng Ge

Molecules 2023, 28(1), 375; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules28010375 - 2 Jan 2023

Cited by 1 | Viewed by 2366

Abstract

Electrochemical reduction of CO₂ to value-added chemicals has been hindered by poor product selectivity and competition from hydrogen evolution reactions. This study aims to unravel the origin of the product selectivity and competitive hydrogen evolution reaction on [MP]⁰ catalysts (M = Fe, Co, Rh and Ir; P is porphyrin ligand) by analyzing the mechanism of CO₂ reduction and H₂ formation based on the results of density functional theory calculations. Reduction of CO₂ to CO and HCOO⁻ proceeds via the formation of carboxylate adduct ([MP-COOH]⁰ and ([MP-COOH]⁻) and metal-hydride [MP-H]⁻, respectively. Competing proton reduction to gaseous hydrogen shares the [MP-H]⁻ intermediate. Our results show that the pK_a of [MP-H]⁰ can be used as an indicator of the CO or HCOO⁻/H₂ preference. Furthermore, an ergoneutral pH has been determined and used to determine the minimum pH at which selective CO₂ reduction to HCOO⁻ becomes favorable over the H₂ production. These analyses allow us to understand the product selectivity of CO₂ reduction on [FeP]⁰, [CoP]⁰, [RhP]⁰ and [IrP]⁰; [FeP]⁰ and [CoP]⁰ are selective for CO whereas [RhP]⁰ and [IrP]⁰ are selective for HCOO⁻ while suppressing H₂ formation. These descriptors should be applicable to other catalysts in an aqueous medium. Full article

(This article belongs to the Special Issue Recent Advance in Transition Metal Complexes and Their Applications)

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15 pages, 3637 KiB

Open AccessArticle

Unsymmetrical Strategy on α-Diimine Nickel and Palladium Mediated Ethylene (Co)Polymerizations

by Xin Ma, Yixin Zhang and Zhongbao Jian

Molecules 2022, 27(24), 8942; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules27248942 - 15 Dec 2022

Cited by 1 | Viewed by 1394

Abstract

Among various catalyst design strategies used in the α-diimine nickel(II) and palladium(II) catalyst systems, the unsymmetrical strategy is an effective and widely utilized method. In this contribution, unsymmetrical nickel and palladium α-diimine catalysts (Ipty/ⁱPr-Ni and Ipty/ⁱPr-Pd) derived from the dibenzobarrelene backbone were constructed via the combination of pentiptycenyl and diisopropylphenyl substituents, and investigated toward ethylene (co)polymerization. Both of these catalysts were capable of polymerizing ethylene in a broad temperature range of 0–120 °C, in which Ipty/ⁱPr-Ni could maintain activity in the level of 10⁶ g mol⁻¹ h⁻¹ even at 120 °C. The branching densities of polyethylenes generated by both nickel and palladium catalysts could be modulated by the reaction temperature. Compared with symmetrical Ipty-Ni and ⁱPr-Ni, Ipty/ⁱPr-Ni exhibited the highest activity, the highest polymer molecular weight, and the lowest branching density. In addition, Ipty/ⁱPr-Pd could produce copolymers of ethylene and methyl acrylate, with the polar monomer incorporating both on the main chain and the terminal of branches. Remarkably, the ratio of the in-chain and end-chain polar monomer incorporations could be modulated by varying the temperature. Full article

(This article belongs to the Special Issue Recent Advance in Transition Metal Complexes and Their Applications)

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9 pages, 2777 KiB

Open AccessArticle

An Iron-NDC Framework with a Cage Structure and an Optothermal Conversion in NIR Window

by Bin Tan, Zhao-Feng Wu and Xiao-Ying Huang

Molecules 2022, 27(24), 8789; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules27248789 - 11 Dec 2022

Cited by 1 | Viewed by 1436

Abstract

Pursuing novel materials with efficient photothermal conversion under irradiation at the near-infrared region windows (NIR, 750–850 nm; NIR-I and NIR-II, 1000–1320 nm)) is of great importance due to their irreplaceable applications, especially in the biomedical field. Herein, on the basis of a coordination chemistry strategy, an iron-based metal-organic framework (MOF) of [N(CH₃)₄]₂[Fe₃(NDC)₄]·DMF·3H₂O (Fe-NDC, 1,4-H₂NDC = 1,4-naphthalenedicarboxylic acid, N(CH₃)₄⁺ = tetramethyl-ammonium, and DMF = N,N-dimethylformamide) was prepared and characterized. Due to the d-d transition effect introduced by coordination with the transition-metal ion of iron and the highly conjugated naphthalenic moiety in 1,4-H₂NDC, guaranteeing an energy transfer between iron and the organic module, Fe-NDC shows a remarkable broad absorption, which could be extended into the NIR-II section. As a result, Fe-NDC could be irradiated by NIR laser (both 808 and 1064 nm) to achieve photothermal conversion. This work sets a good example to inspire the future designation of NIR light-irradiated photothermal materials based on the first-row transition metals. Full article

(This article belongs to the Special Issue Recent Advance in Transition Metal Complexes and Their Applications)

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15 pages, 4337 KiB

Open AccessArticle

Silver(I) Complexes Based on Oxadiazole-Functionalized α-Aminophosphonate: Synthesis, Structural Study, and Biological Activities

by Shaima Hkiri, Kübra Açıkalın Coşkun, Elvan Üstün, Ali Samarat, Yusuf Tutar, Neslihan Şahin and David Sémeril

Molecules 2022, 27(23), 8131; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules27238131 - 22 Nov 2022

Cited by 6 | Viewed by 1831

Abstract

Two silver(I) complexes, bis{diethyl[(5-phenyl-1,3,4-oxadiazol-2-yl-κN³:κN⁴-amino) (4-trifluoromethylphenyl)methyl]phosphonate-(tetrafluoroborato-κF)}-di-silver(I) and tetrakis-{diethyl[(5-phenyl-1,3,4-oxadiazol-2-yl-κN³-amino)(4-trifluoromethylphenyl)methyl]phosphonate} silver(I) tetrafluoroborate, were prepared starting from the diethyl[(5-phenyl-1,3,4-oxadiazol-2-yl-amino)(4-trifluoromethylphenyl)methyl]phosphonate (1) ligand and AgBF₄ salt in Ag/ligand ratios of 1/1 and 1/4, respectively. The structure, stoichiometry, and geometry of the silver complexes were fully characterized by elemental analyses, infrared, single-crystal X-ray diffraction studies, multinuclear NMR, and mass spectroscopies. The binuclear complex ([Ag₂(1)₂(BF₄)₂]; 2) crystallizes in the monoclinic asymmetric space group P2₁/c and contains two silver atoms adopting a {AgN₂F} planar trigonal geometry, which are simultaneously bridged by two oxadiazole rings of two ligands, while the mononuclear complex ([Ag(1)₄]BF₄; 3) crystallizes in the non-usual cubic space group Fd-3c in which the silver atom binds to four distinct electronically enriched nitrogen atoms of the oxadiazole ring, in a slightly distorted {AgN₄} tetrahedral geometry. The α-aminophosphonate and the monomeric silver complex were evaluated in vitro against MCF-7 and PANC-1 cell lines. The silver complex is promising as a drug candidate for breast cancer and the pancreatic duct with half-maximal inhibitory concentration (IC₅₀) values of 8.3 ± 1.0 and 14.4 ± 0.6 μM, respectively. Additionally, the interactions of the ligand and the mononuclear complex with Vascular Endothelial Growth Factor Receptor-2 and DNA were evaluated by molecular docking methods. Full article

(This article belongs to the Special Issue Recent Advance in Transition Metal Complexes and Their Applications)

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11 pages, 2719 KiB

Open AccessArticle

Synthesis and Characterization of New Ruthenium (II) Complexes of Stoichiometry [Ru(p-Cymene)Cl₂L] and Their Cytotoxicity against HeLa-Type Cancer Cells

by Marta G. Fuster, Imane Moulefera, Mercedes G. Montalbán, José Pérez, Gloria Víllora and Gabriel García

Molecules 2022, 27(21), 7264; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules27217264 - 26 Oct 2022

Viewed by 2043

Abstract

When the [Ru(p-cymene)(μ-Cl)Cl]₂ complex is made to react, in dichloromethane, with the following ligands: 2-aminobenzonitrile (2abn), 4-aminobenzonitrile (4abn), 2-aminopyridine (2ampy) and 4-aminopyridine (4ampy), after addition of hexane, the following compounds are obtained: [Ru(p-cymene)Cl₂(2abn)] (I), [Ru(p-cymene)Cl₂(4abn)] (II), [Ru(p-cymene)Cl₂(2ampy] (III) and [Ru(p-cymene)Cl₂(μ-(4ampy)] (IV). All the compounds are characterized by elemental analysis of carbon, hydrogen and nitrogen, proton nuclear magnetic resonance, COSY ¹H-¹H, high-resolution mass spectrometry (ESI), thermogravimetry and single-crystal X-ray diffraction (the crystal structure of III is reported and compared with the closely related literature of II). The cytotoxicity effects of complexes were described for cervical cancer HeLa cells via 3-(4.5-dimethylthiazol-2-yl)-2.5-diphenyltetrazolium bromide (MTT) assay. The results demonstrate a low in vitro anticancer potential of the complexes. Full article

(This article belongs to the Special Issue Recent Advance in Transition Metal Complexes and Their Applications)

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