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Nitrogen Ligands

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

Deadline for manuscript submissions: closed (30 November 2023) | Viewed by 29429

Special Issue Editors

Prof. Dr. Mário J. F. Calvete

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Guest Editor
Centro de Química de Coimbra (CQC), Department of Chemistry, University of Coimbra, Rua Larga, 3004-535 Coimbra, Portugal
Prof. Dr. Mariette M. Pereira

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Guest Editor
Department of Chemistry, University of Coimbra, Coimbra, Portugal
Interests: organic synthesis; CO2-based polymeric materials; medicinal chemistry; sustained catalytic processes
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Nitrogen containing ligands (abbreviated as N-Ligands) enjoy a prominent role in many aspects of Chemistry, namely in Coordination Chemistry, Metal-Organic Chemistry, Inorganic and Bioinorganic Chemistry, Biomedicinal Chemistry, Bioconjugate Chemistry, Materials Chemistry, Catalysis (both homogeneous and heterogeneous), Supramolecular Chemistry, among other multidisciplinary fields were N-Ligands are central.

This special issue aims to provide a global view on the synthesis, properties and applications involving this type of ligands, considering approaches from the fundamental to applied ones, including multidisciplinary studies.

It is a great pleasure to invite you to participate in this Special Issue, disseminating your work in form of communication, full paper and reviews on the abovementioned or related topics.

Prof. Dr. Mário J. F. Calvete
Prof. Dr. Mariette M. Pereira
Guest Editors

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Keywords

  • N-ligands
  • Organic synthesis
  • Coordination chemistry
  • Metal–organic chemistry
  • Inorganic and bioinorganic chemistry
  • Biomedicinal chemistry
  • Bioconjugate chemistry
  • Materials chemistry
  • Homogeneous catalysis
  • Heterogeneous catalysis
  • Supramolecular chemistry

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Published Papers (9 papers)

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Research

16 pages, 2966 KiB  
Article
Synthesis, Characterization, and Reactivity Studies of New Cyclam-Based Y(III) Complexes
by Filipe Madeira, Luis F. Veiros, Luis G. Alves and Ana M. Martins
Molecules 2023, 28(24), 7998; https://doi.org/10.3390/molecules28247998 - 7 Dec 2023
Viewed by 1344
Abstract
[(Bn2Cyclam)Y(N(SiMe3)2)] was prepared by reaction of H2Bn2Cyclam with Y[N(SiMe3)2]3. The protonation of the macrocycle ligand in [(Bn2Cyclam)Y(N(SiMe3)2)] is observed upon reaction [...] Read more.
[(Bn2Cyclam)Y(N(SiMe3)2)] was prepared by reaction of H2Bn2Cyclam with Y[N(SiMe3)2]3. The protonation of the macrocycle ligand in [(Bn2Cyclam)Y(N(SiMe3)2)] is observed upon reaction with [HNMe3][BPh4] leading to the formation of [(HBn2Cyclam)Y(N(SiMe3)2)][BPh4]. DFT analysis of [(Bn2Cyclam)Y(N(SiMe3)2)] showed that the HOMO is located on the anionic nitrogen atoms of the cyclam ring indicating that protonation follows orbital control. Addition of H2Bn2Cyclam and H2(3,5-tBu2Bn)2Cyclam to a 1:3 mixture of YCl3 and LiCH2SiMe3 in THF resulted in the formation of [((C6H4CH2)BnCyclam)Y(THF)(µ-Cl)Li(THF)2] and [Y{(η3-3,5-tBu2Bn)2Cyclam}Li(THF)], respectively. The reaction of H23,5-tBu2Bn2Cyclam with Y(CH2SiMe3)3(THF)2 was studied and monitored by a temperature variation NMR experiment revealing the formation of [(3,5-tBu2Bn2Cyclam)Y(CH2SiMe3)]. Preliminary catalytic assays have shown that [Y{(η3-3,5-tBu2Bn)2Cyclam}Li(THF)] is a very efficient catalyst for the intramolecular hydroamination of 2,2-diphenyl-pent-4-enylamine. Full article
(This article belongs to the Special Issue Nitrogen Ligands)
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19 pages, 7122 KiB  
Article
Enhancing Visible-Light Photocatalysis with Pd(II) Porphyrin-Based TiO2 Hybrid Nanomaterials: Preparation, Characterization, ROS Generation, and Photocatalytic Activity
by Dawid Malec, Marta Warszyńska, Paweł Repetowski, Anton Siomchen and Janusz M. Dąbrowski
Molecules 2023, 28(23), 7819; https://doi.org/10.3390/molecules28237819 - 28 Nov 2023
Cited by 2 | Viewed by 1596
Abstract
Novel hybrid TiO2-based materials were obtained by adsorption of two different porphyrins on the surface of nanoparticles—commercially available 5,10,15,20-tetrakis(4-sulfonatophenyl)porphyrin (TPPS) and properly modified metalloporphyrin—5,10,15,20-tetrakis(2,6-difluoro-3-sulfophenyl)porphyrin palladium(II) (PdF2POH). The immobilization of porphyrins on the surface of TiO2 was possible due [...] Read more.
Novel hybrid TiO2-based materials were obtained by adsorption of two different porphyrins on the surface of nanoparticles—commercially available 5,10,15,20-tetrakis(4-sulfonatophenyl)porphyrin (TPPS) and properly modified metalloporphyrin—5,10,15,20-tetrakis(2,6-difluoro-3-sulfophenyl)porphyrin palladium(II) (PdF2POH). The immobilization of porphyrins on the surface of TiO2 was possible due to the presence of sulfonyl groups. To further elevate the adsorption of porphyrin, an anchoring linker—4-hydroxybenzoic acid (PHBA)—was used. The synthesis of hybrid materials was proven by electronic absorption spectroscopy, dynamic light scattering (DLS), and photoelectrochemistry. Results prove the successful photosensitization of TiO2 to visible light by both porphyrins. However, the presence of the palladium ion in the modifier structure played a key role in strong adsorption, enhanced charge separation, and thus effective photosensitization. The incorporation of halogenated metalloporphyrins into TiO2 facilitates the enhancement of the comprehensive characteristics of the investigated materials and enables the evaluation of their performance under visible light. The effectiveness of reactive oxygen species (ROS) generation was also determined. Porphyrin-based materials with the addition of PHBA seemed to generate ROS more effectively than other composites. Interestingly, modifications influenced the generation of singlet oxygen for TPPS but not hydroxyl radical, in contrast to PdF2POH, where singlet oxygen generation was not influenced but hydroxyl radical generation was increased. Palladium (II) porphyrin-modified materials were characterized by higher photostability than TPPS-based nanostructures, as TPPS@PHBA-P25 materials showed the highest singlet oxygen generation and may be oxidized during light exposure. Photocatalytic activity tests with two model pollutants—methylene blue (MB) and the opioid drug tramadol (TRML)—confirmed the light dose-dependent degradation of those two compounds, especially PdF2POH@P25, which led to the virtually complete degradation of MB. Full article
(This article belongs to the Special Issue Nitrogen Ligands)
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15 pages, 2111 KiB  
Article
A Comparative Evaluation of the Photosensitizing Efficiency of Porphyrins, Chlorins and Isobacteriochlorins toward Melanoma Cancer Cells
by Kelly A. D. F. Castro, Nuno M. M. Moura, Mário M. Q. Simões, Mariana M. Q. Mesquita, Loyanne C. B. Ramos, Juliana C. Biazzotto, José A. S. Cavaleiro, M. Amparo F. Faustino, Maria Graça P. M. S. Neves and Roberto S. da Silva
Molecules 2023, 28(12), 4716; https://doi.org/10.3390/molecules28124716 - 12 Jun 2023
Cited by 6 | Viewed by 1744
Abstract
Skin cancer is one of the cancers that registers the highest number of new cases annually. Among all forms of skin cancer, melanoma is the most invasive and deadliest. The resistance of this form of cancer to conventional treatments has led to the [...] Read more.
Skin cancer is one of the cancers that registers the highest number of new cases annually. Among all forms of skin cancer, melanoma is the most invasive and deadliest. The resistance of this form of cancer to conventional treatments has led to the employment of alternative/complementary therapeutic approaches. Photodynamic therapy (PDT) appears to be a promising alternative to overcome the resistance of melanoma to conventional therapies. PDT is a non-invasive therapeutic procedure in which highly reactive oxygen species (ROS) are generated upon excitation of a photosensitizer (PS) when subjected to visible light of an adequate wavelength, resulting in the death of cancer cells. In this work, inspired by the efficacy of tetrapyrrolic macrocycles to act as PS against tumor cells, we report the photophysical characterization and biological assays of isobacteriochlorins and their corresponding chlorins and porphyrins against melanoma cancer cells through a photodynamic process. The non-tumoral L929 fibroblast murine cell line was used as the control. The results show that the choice of adequate tetrapyrrolic macrocycle-based PS can be modulated to improve the performance of PDT. Full article
(This article belongs to the Special Issue Nitrogen Ligands)
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17 pages, 2024 KiB  
Article
Field-Induced Single-Ion Magnet Behavior in Nickel(II) Complexes with Functionalized 2,2′:6′-2″-Terpyridine Derivatives: Preparation and Magneto-Structural Study
by Francisco Ramón Fortea-Pérez, Julia Vallejo, Teresa F. Mastropietro, Giovanni De Munno, Renato Rabelo, Joan Cano and Miguel Julve
Molecules 2023, 28(11), 4423; https://doi.org/10.3390/molecules28114423 - 29 May 2023
Cited by 5 | Viewed by 7824
Abstract
Two mononuclear nickel(II) complexes of the formula [Ni(terpyCOOH)2](ClO4)2∙4H2O (1) and [Ni(terpyepy)2](ClO4)2 MeOH (2) [terpyCOOH = 4′-carboxyl-2,2′:6′,2″-terpyridine and terpyepy = 4′-[(2-pyridin-4-yl)ethynyl]-2,2′:6′,2″-terpyridine] have been prepared and their structures [...] Read more.
Two mononuclear nickel(II) complexes of the formula [Ni(terpyCOOH)2](ClO4)2∙4H2O (1) and [Ni(terpyepy)2](ClO4)2 MeOH (2) [terpyCOOH = 4′-carboxyl-2,2′:6′,2″-terpyridine and terpyepy = 4′-[(2-pyridin-4-yl)ethynyl]-2,2′:6′,2″-terpyridine] have been prepared and their structures determined by single-crystal X-ray diffraction. Complexes 1 and 2 are mononuclear compounds, where the nickel(II) ions are six-coordinate by the six nitrogen atoms from two tridentate terpy moieties. The mean values of the equatorial Ni-N bond distances [2.11(1) and 2.12(1) Å for Ni(1) at 1 and 2, respectively, are somewhat longer than the axial ones [2.008(6) and 2.003(6) Å (1)/2.000(1) and 1.999(1) Å (2)]. The values of the shortest intermolecular nickel–nickel separation are 9.422(1) (1) and 8.901(1) Å (2). Variable-temperature (1.9–200 K) direct current (dc) magnetic susceptibility measurements on polycrystalline samples of 1 and 2 reveal a Curie law behavior in the high-temperature range, which corresponds to magnetically isolated spin triplets, the downturn of the χMT product at lower temperatures being due to zero-field splitting effects (D). Values of D equal to −6.0 (1) and −4.7 cm−1 (2) were obtained through the joint analysis of the magnetic susceptibility data and the field dependence of the magnetization. These results from magnetometry were supported by theoretical calculations. Alternating current (ac) magnetic susceptibility measurements of 1 and 2 in the temperature range 2.0–5.5 K show the occurrence of incipient out-phase signals under applied dc fields, a phenomenon that is characteristic of field-induced Single-Molecule Magnet (SMM) behavior, which herein concerns the 2 mononuclear nickel(II) complexes. This slow relaxation of the magnetization in 1 and 2 has its origin in the axial compression of the octahedral surrounding at their nickel(II) ions that leads to negative values of D. A combination of an Orbach and a direct mechanism accounts for the field-dependent relation phenomena in 1 and 2. Full article
(This article belongs to the Special Issue Nitrogen Ligands)
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29 pages, 6922 KiB  
Article
Tuning Photophysical Properties by p-Functional Groups in Zn(II) and Cd(II) Complexes with Piperonylic Acid
by Francisco Sánchez-Férez, Joaquim Mª Rius-Bartra, José A. Ayllón, Teresa Calvet, Mercè Font-Bardia and Josefina Pons
Molecules 2022, 27(4), 1365; https://doi.org/10.3390/molecules27041365 - 17 Feb 2022
Cited by 15 | Viewed by 2696
Abstract
Aggregation between discrete molecules is an essential factor to prevent aggregation-caused quenching (ACQ). Indeed, functional groups capable of generating strong hydrogen bonds are likely to assemble and cause ACQ and photoinduced electron transfer processes. Thus, it is possible to compare absorption and emission [...] Read more.
Aggregation between discrete molecules is an essential factor to prevent aggregation-caused quenching (ACQ). Indeed, functional groups capable of generating strong hydrogen bonds are likely to assemble and cause ACQ and photoinduced electron transfer processes. Thus, it is possible to compare absorption and emission properties by incorporating two ligands with a different bias toward intra- and intermolecular interactions that can induce a specific structural arrangement. In parallel, the π electron-donor or electron-withdrawing character of the functional groups could modify the Highest Ocuppied Molecular Orbital (HOMO)–Lowest Unocuppied Molecular Orbital (LUMO) energy gap. Reactions of M(OAc)2·2H2O (M = Zn(II) and Cd(II); OAc = acetate) with 1,3-benzodioxole-5-carboxylic acid (Piperonylic acid, HPip) and 4-acetylpyridine (4-Acpy) or isonicotinamide (Isn) resulted in the formation of four complexes. The elucidation of their crystal structure showed the formation of one paddle-wheel [Zn(μ-Pip)2(4-Acpy)]2 (1); a mixture of one dimer and two monomers [Zn(µ-Pip)(Pip)(Isn)2]2·2[Zn(Pip)2(HPip)(Isn)]·2MeOH (2); and two dimers [Cd(μ-Pip)(Pip)(4-Acpy)2]2 (3) and [Cd(μ-Pip)(Pip)(Isn)2]2·MeOH (4). They exhibit bridged (1, µ2-η1:η1), bridged, chelated and monodentated (2, µ2-η1:η1, µ1-η1:η1 and µ1-η1), or simultaneously bridged and chelated (3 and 4, µ2-η2:η1) coordination modes. Zn(II) centers accommodate coordination numbers 5 and 6, whereas Cd(II) presents coordination number 7. We have related their photophysical properties and fluorescence quantum yields with their geometric variations and interactions supported by TD-DFT calculations. Full article
(This article belongs to the Special Issue Nitrogen Ligands)
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19 pages, 2438 KiB  
Article
Synthesis of Computationally Designed 2,5(6)-Benzimidazole Derivatives via Pd-Catalyzed Reactions for Potential E. coli DNA Gyrase B Inhibition
by Rafael T. Aroso, Rita C. Guedes and Mariette M. Pereira
Molecules 2021, 26(5), 1326; https://doi.org/10.3390/molecules26051326 - 2 Mar 2021
Cited by 5 | Viewed by 3360
Abstract
A pharmacophore model for inhibitors of Escherichia coli’s DNA Gyrase B was developed, using computer-aided drug design. Subsequently, docking studies showed that 2,5(6)-substituted benzimidazole derivatives are promising molecules, as they possess key hydrogen bond donor/acceptor groups for an efficient interaction with this [...] Read more.
A pharmacophore model for inhibitors of Escherichia coli’s DNA Gyrase B was developed, using computer-aided drug design. Subsequently, docking studies showed that 2,5(6)-substituted benzimidazole derivatives are promising molecules, as they possess key hydrogen bond donor/acceptor groups for an efficient interaction with this bacterial target. Furthermore, 5(6)-bromo-2-(2-nitrophenyl)-1H-benzimidazole, selected as a core molecule, was prepared on a multi-gram scale through condensation of 4-bromo-1,2-diaminobenzene with 2-nitrobenzaldehyde using a sustainable approach. The challenging functionalization of the 5(6)-position was carried out via palladium-catalyzed Suzuki–Miyaura and Buchwald-Hartwig amination cross-coupling reactions between N-protected-5-bromo-2-nitrophenyl-benzimidazole and aryl boronic acids or sulfonylanilines, with yields up to 81%. The final designed molecules (2-(aminophen-2-yl)-5(6)-substituted-1H-benzimidazoles), which encompass the appropriate functional groups in the 5(6)-position according to the pharmacophore model, were obtained in yields up to 91% after acid-mediated N-boc deprotection followed by Pd-catalyzed hydrogenation. These groups are predicted to favor interactions with DNA gyrase B residues Asn46, Asp73, and Asp173, aiming to promote an inhibitory effect. Full article
(This article belongs to the Special Issue Nitrogen Ligands)
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14 pages, 2783 KiB  
Article
Click Conjugation of Boron Dipyrromethene (BODIPY) Fluorophores to EGFR-Targeting Linear and Cyclic Peptides
by Tyrslai M. Williams, Nichole E. M. Kaufman, Zehua Zhou, Sitanshu S. Singh, Seetharama D. Jois and Maria da Graça H. Vicente
Molecules 2021, 26(3), 593; https://doi.org/10.3390/molecules26030593 - 23 Jan 2021
Cited by 6 | Viewed by 3481
Abstract
Through a simple 1,3-cycloaddition reaction, three BODIPY-peptide conjugates that target the extracellular domain of the epidermal growth factor receptor (EGFR) were prepared and their ability for binding to EGFR was investigated. The peptide ligands K(N3)LARLLT and its cyclic analog cyclo(K(N3 [...] Read more.
Through a simple 1,3-cycloaddition reaction, three BODIPY-peptide conjugates that target the extracellular domain of the epidermal growth factor receptor (EGFR) were prepared and their ability for binding to EGFR was investigated. The peptide ligands K(N3)LARLLT and its cyclic analog cyclo(K(N3)larllt, previously shown to have high affinity for binding to the extracellular domain of EGFR, were conjugated to alkynyl-functionalized BODIPY dyes 1 and 2 via a copper-catalyzed click reaction. This reaction produced conjugates 3, 4, and 5 in high yields (70–82%). In vitro studies using human carcinoma HEp2 cells that overexpress EGFR demonstrated high cellular uptake, particularly for the cyclic peptide conjugate 5, and low cytotoxicity in light (~1 J·cm−2) and darkness. Surface plasmon resonance (SPR) results show binding affinity of the three BODIPY-peptide conjugates for EGFR, particularly for 5 bearing the cyclic peptide. Competitive binding studies using three cell lines with different expressions of EGFR show that 5 binds specifically to EGFR-overexpressing colon cancer cells. Among the three conjugates, 5 bearing the cyclic peptide exhibited the highest affinity for binding to the EGFR protein. Full article
(This article belongs to the Special Issue Nitrogen Ligands)
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10 pages, 2465 KiB  
Article
Synthesis of Iron(II)–N-Heterocyclic Carbene Complexes: Paving the Way for a New Class of Antibiotics
by Carolina S. Vinagreiro, Rita Lopes, Beatriz Royo, Gabriela Jorge Da Silva and Mariette M. Pereira
Molecules 2020, 25(12), 2917; https://doi.org/10.3390/molecules25122917 - 24 Jun 2020
Cited by 6 | Viewed by 2824
Abstract
The synthesis and structural modulation of five pro-ligand salts was achieved using alternative sustainable synthetic strategies, the use of microwaves being the method of choice, with an 81% yield and an E factor of 43 for 3d. After complexation with Fe3 [...] Read more.
The synthesis and structural modulation of five pro-ligand salts was achieved using alternative sustainable synthetic strategies, the use of microwaves being the method of choice, with an 81% yield and an E factor of 43 for 3d. After complexation with Fe3(CO)12 by direct reaction with the appropriate pro-ligands at 130 °C, a set of iron(II) N-heterocyclic carbene (NHC) complexes were isolated and fully characterized (via 1H and 13C NMR and IR spectroscopy and elemental analysis). The antibacterial activities of the iron(II)-NHC complexes were tested against standard World Health Organization priority bacterial strains: Staphylococcus aureus ATCC 29213 and Escherichia coli ATCC 25922. The results showed a significant effect of the Fe(II)-NHC side-chain on the antibacterial activity against both Gram-negative and Gram-positive bacteria. Among all compounds, the most lipophilic iron complex, 3b, was found to be the most active one, with a minimum inhibitory concentration of 8 µg/mL. Pioneering mechanistic studies suggested an alternative mechanism of action (OH· formation), which opens the way for the development of a new class of antibiotics. Full article
(This article belongs to the Special Issue Nitrogen Ligands)
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13 pages, 1863 KiB  
Article
Syntheses, Reactivities, Characterization, and Crystal Structures of Dipalladium Complexes Containing the 1,3-pyrimidinyl Ligand: Structures of [Pd(PPh3)(Br)]2(μ,η2-C4H3N2)2, [Pd(Br)]2(μ,η2-Hdppa)2, and [{Pd(PPh3)(CH3CN)}2(μ,η2-C4H3N2)2][BF4]2
by Hsiao-Fen Wang, Kuang-Hway Yih and Gene-Hsiang Lee
Molecules 2020, 25(9), 2035; https://doi.org/10.3390/molecules25092035 - 27 Apr 2020
Viewed by 2890
Abstract
In a refluxing chloroform solution, the η1-pyrimidinyl {pyrimidinyl = C4H3N2} palladium complex [Pd(PPh3)2(η1-C4H3N2)(Br)], 1 exhibited intermolecular displacement of two triphenylphosphine ligands to form [...] Read more.
In a refluxing chloroform solution, the η1-pyrimidinyl {pyrimidinyl = C4H3N2} palladium complex [Pd(PPh3)2(η1-C4H3N2)(Br)], 1 exhibited intermolecular displacement of two triphenylphosphine ligands to form the doubly bridged η2-pyrimidinyl Dipalladium complex [Pd(PPh3)(Br)]2(μ,η2-C4H3N2)2, 3. The treatment of 1 with Hdppa {Hdppa = N,N-bisdiphenyl phosphinoamine} in refluxing dichloromethane yielded the doubly bridged Hdppa dipalladium complex [Pd(Br)]2(μ,η2-Hdppa)2, 4. Complex 1 reacted with the bidentate ligand, NH4S2CNC4H8 and, NaS2COEt, and the tridentate ligand, KTp {Tp = tris(pyrazoyl-1-yl)borate}, to form the η2-dithio η1-pyrimidinyl complex [Pd(PPh3)(η1-C4H3N2)(η2-SS)], (5: SS = S2CNC4H8; 6: SS = S2COEt) and η2-Tp η1-pyrimidinyl complex [Pd(PPh3)(η1-C4H3N2)(η2-Tp)], 7, respectively. Treatment of 1 with AgBF4 in acetonitrile at room temperature resulted in the formation of the doubly bridged η2-pyrimidinyl dipalladium complex [{Pd(PPh3)(CH3CN)}2(μ,η2-C4H3N2)2][BF4]2, 8. All of the complexes were identified using spectroscopic methods, and complexes 3, 4, and 8 were determined using single-crystal X-ray diffraction analyses. Full article
(This article belongs to the Special Issue Nitrogen Ligands)
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