Tetraaza macrocyclic Schiff base metal complexes bearing pendant groups: Synthesis, characterization and bioactivity studies

Paulpandiyan, Rajakkani; Arunadevi, Alagarraj; Andavan, Gurusamy Thangavelu Senthil

doi:10.1016/j.inoche.2021.108989

Cited by 18 publications

(6 citation statements)

References 63 publications

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“…Thus, they give stable metal complexes with many metal ions. Macrocyclic Schiff bases are used in the fields of biochemistry [ 1 , 2 , 3 ], supramolecular chemistry [ 4 , 5 ], materials science [ 6 ], molecular recognition [ 7 , 8 ], and catalysis [ 9 , 10 ].…”

Section: Introductionmentioning

confidence: 99%

Experimental and Theoretical Studies of the Optical Properties of the Schiff Bases and Their Materials Obtained from o-Phenylenediamine

et al. 2022

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Two macrocyclic Schiff bases derived from o-phenylenediamine and 2-hydroxy-5-methylisophthalaldehyde L1 or 2-hydroxy-5-tert-butyl-1,3-benzenedicarboxaldehyde L2, respectively, were obtained and characterized by X-ray crystallography and spectroscopy (UV-vis, fluorescence and IR). X-ray crystal structure determination and DFT calculations for compounds confirmed their geometry in solution and in the solid phase. Moreover, intermolecular interactions in the crystal structure of L1 and L2 were analyzed using 3D Hirshfeld surfaces and the related 2D fingerprint plots. The 3D Hirschfeld analyses show that the most numerous interactions were found between hydrogen atoms. A considerable number of such interactions are justified by the presence of bulk tert-butyl groups in L2. The luminescence of L1 and L2 in various solvents and in the solid state was studied. In general, the quantum efficiency between 0.14 and 0.70 was noted. The increase in the quantum efficiency with the solvent polarity in the case of L1 was observed (λex = 350 nm). For L2, this trend is similar, except for the chloroform. In the solid state, emission was registered at 552 nm and 561 nm (λex = 350 nm) for L1 and L2, respectively. Thin layers of the studied compounds were deposited on Si(111) by the spin coating method or by thermal vapor deposition and studied by scanning electron microscopy (SEM/EDS), atomic force microscopy (AFM), spectroscopic ellipsometry and fluorescence spectroscopy. The ellipsometric analysis of thin materials obtained by thermal vapor deposition showed that the band-gap energy was 3.45 ± 0.02 eV (359 ± 2 nm) and 3.29 ± 0.02 eV (377 ± 2 nm) for L1/Si and L2/Si samples, respectively. Furthermore, the materials of the L1/Si and L2/Si exhibited broad emission. This feature can allow for using these compounds in LED diodes.

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Section: Introductionmentioning

confidence: 99%

Experimental and Theoretical Studies of the Optical Properties of the Schiff Bases and Their Materials Obtained from o-Phenylenediamine

et al. 2022

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“…After 20 min, a 6 mm well got cut at the center of agar plates and each well were lled with prepared samples of synthesized complexes, keeping solvent media having Gentamycin as + ive control and solvent media alone as -ive control. Each plate was analyzed for measuring the zone of inhibition after 20 hr of incubation at 37 C and for fungus, zone of inhibition was measured after incubation for 48 hr at 28 C [25][26][27].…”

Section: Biological Activitymentioning

confidence: 99%

Phenyl conjugation effect on Fe3+/2+ formal potential of FeN4-macryclic complex

Ravinder

Das

Kumar

2023

J Incl Phenom Macrocycl Chem

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The monitoring of shifting of the redox potential of macrocyclic complexes towards anodic or cathodic regions, which acts as a mediator in many electrocatalytic events, is made possible by inserting electron donating or withholding groups into their frameworks. Herein, using a template strategy, two [14]membered N 4 -macrocyclic complexes (denoted as complex A and complex B) with similar molecular cores but different phenyl moieties were prepared and characterized using multiple characterization techniques. The characterization results suggested a saddle-shaped geometry for these complexes, which might be due to the steric repulsions between the benzenoid and amidic moieties on the macrocyclic framework, as also supported by theoretical computations. Further, to investigate the electrochemical behaviors of these complexes, cyclic voltammetry was used and found that the Fe 3+/2+ redox potential was systematically shifted in anodic direction with the increment of phenyl moieties on the [14]-membered N 4 -macrocyclic core. DFT calculations indicated the down-shifting in the most occupied molecular orbital due to the increased phenyl conjugation, which could be correlated with the shifting of Fe 3+/2+ redox potential. Biological evaluation of these complexes has also been carried out.

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“…Rajakkani et al, (2021) [ 60 ] reported the synthesis and biological evaluation of stable mononuclear metal (II) complexes (specifically, Co, Ni, and Zn) with an unsymmetrical 13-membered Knoevenagel macrocyclic SB ligand. Antimicrobial activity was determined by using the well dilution method against bacteria (two Gram-positive, Staphylococcus aureus , Bacillus subtilis , and three Gram-negative, Escherichia coli , Klebsiella pneumoniae , Salmonella typhi ) compared with the standard kanamycin (MIC = 1.4, 1.2, 1.8, 2.2 and 2.0 µM, respectively) and fungi ( Aspergillus niger , Fusarium solani , Aspergillus flavus , Rhizoctonia bataticola , Candida albicans ) compared with the standard fluconazole (MIC = 1.2, 1.5, 1.2, 1.8 and 1.8 µM, respectively).…”

Section: Mononuclear Sbs Complexesmentioning

confidence: 99%

Metal Complexes with Schiff Bases: Data Collection and Recent Studies on Biological Activities

Sinicropi

Ceramella

Iacopetta

et al. 2022

IJMS

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Metal complexes play a crucial role in pharmaceutical sciences owing to their wide and significant activities. Schiff bases (SBs) are multifaceted pharmacophores capable of forming chelating complexes with various metals in different oxidation states. Complexes with SBs are extensively studied for their numerous advantages, including low cost and simple synthetic strategies. They have been reported to possess a variety of biological activities, including antimicrobial, anticancer, antioxidant, antimalarial, analgesic, antiviral, antipyretic, and antidiabetic ones. This review summarizes the most recent studies on the antimicrobial and antiproliferative activities of SBs-metal complexes. Moreover, recent studies regarding mononuclear and binuclear complexes with SBs are described, including antioxidant, antidiabetic, antimalarial, antileishmanial, anti-Alzheimer, and catecholase activities.

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Tetraaza macrocyclic Schiff base metal complexes bearing pendant groups: Synthesis, characterization and bioactivity studies

Cited by 18 publications

References 63 publications

Experimental and Theoretical Studies of the Optical Properties of the Schiff Bases and Their Materials Obtained from o-Phenylenediamine

Experimental and Theoretical Studies of the Optical Properties of the Schiff Bases and Their Materials Obtained from o-Phenylenediamine

Phenyl conjugation effect on Fe3+/2+ formal potential of FeN4-macryclic complex

Metal Complexes with Schiff Bases: Data Collection and Recent Studies on Biological Activities

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