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Öğe Alkyl chain modified metalophthalocyanines with enhanced antioxidant-antimicrobial properties by doping Ag+ and Pd2+ ions(Elsevier, 2022) Alici, Esma Hande; Bilgicli, Ahmet T.; Tuzun, Burak; Gunsel, Armagan; Arabaci, Gulnur; Yarasir, M. NiluferIn this study, we report the synthesis and characterization of peripheral alkyl chain-substituted metalophthalocyanines [CuPc (3) , ZnPc (4) , and CoPc (5) ] as optically sensitive substances with antifungal and antibacterial properties. Synthesized compounds were characterized by using common spectroscopic methods such as H-1 NMR, C-13 NMR, FT-IR, MALDI-TOF, fluorescence, and UV-Vis spectroscopy. Aggregation behaviors of phthalocyanines in the presence of Ag+ and Pd2+ ions were investigated by UV-Vis and fluorescence spectroscopy. The quenching capacity of Ag+ and Pd2+ ions for (4) was calculated from the Stern-Volmer equation and was found to be 9.76 x 10(4) mol/L and 2.86 x 10(5) mol/L for Pd2+ and Ag+ ions, respectively. The binding stoichiometry (n) and binding constant (K-a) of (4) for Ag+and Pd2+ ions were calculated by the changed Benesi-Hildebrand equation. K-a value of (4) for Ag+ and Pd2+ ions are 2.57 x 10(9) M-1 and 1.44 x 10(8) M-1 , respectively. The binding ratio of (4) for Ag+ and Pd2+ ions is 1.83 and 1.68, respectively. The morphological features of phthalocyanine derivatives were examined before and after the Ag + or Pd(2+)ions treatment by scanning electron microscopy (SEM). In addition, the antioxidant efficiencies of newly synthesized metalophthalocyanines and their Ag+ and Pd2+ ion-doped aggregates were evaluated using different methods such as DPPH free radical scavenging, iron ion chelating, and reducing power activities. The chemical and biological activities of phthalonitrile and its metalophthalocyanines were also evaluated by DFT and molecular docking calculations. Finally, the antifungal and antibacterial efficiencies of newly synthesized beta-substituted phthalocyanines and their Ag+ and Pd2+ ion-doped forms were investigated using macrobroth dilution and disk diffusion methods. (c) 2022 Elsevier B.V. All rights reserved.Öğe Comparison of spectroscopic, electronic, theoretical, optical and surface morphological properties of functional manganese(III) phthalocyanine compounds for various conditions(ELSEVIER SCIENCE BV, 2019) Gunsel, Armagan; Bilgich, Ahmet T.; Piskin, Hasan; Tuzun, Burak; Delibas, Nagihan Caylak; Yarasir, M. Nilufer; Gunduz, BayramWe synthesized and characterized the non-peripherally and peripherally tetra-substituted manganese (III) phthalocyanines (3) and (4) containing [4-(2-methoxyethyl)phenoxy] group. Synthesized compounds were characterized by standard spectroscopy methods. The crystallographic information and stabilization dynamics of supramolecular structure of intended compound (2) have been revealed by the analysis of single-crystal X-ray diffraction measurements. The optical, sensing, conductance and electrical properties were investigated. The absorption band edge values of the (MnClPc)-Cl-III (3) are lower than that of the (MnClPc)-Cl-III (4). The optical band gaps of the (MnClPc)-Cl-III (3) and (MnClPc)-Cl-III (4) display direct allowed optical band gap and semiconductor behaviour. The refractive indices of the functional manganese(III) phthalocyanine compounds give significant results for preparation of diodes and sensor devices. The surface morphological properties of the (MnClPc)-Cl-III (3) and (4) films were investigated under different conditions. Finally, quantum chemical parameters of the synthesized compounds were calculated using quantum chemical calculations. The calculated Infrared spectroscopy, Nuclear Magnetic Resonance, and UV-Vis spectra of all compounds were investigated and the obtained parameters were compared with experimental values. (C) 2019 Elsevier B.V. All rights reserved.Öğe Evaluation of the effects of newly synthesized metallophthalocyanines on breast cancer cell lines with photodynamic therapy (vol 51, pg 15996, 2022)(Royal Soc Chemistry, 2023) Bostanci, Hayrani Eren; Bilgicli, Ahmet T. T.; Guzel, Emre; Gunsel, Armagan; Hepokur, Ceylan; cimen, Behzat; Yarasir, M. NiluferCorrection for 'Evaluation of the effects of newly synthesized metallophthalocyanines on breast cancer cell lines with photodynamic therapy' by Hayrani Eren Bostanc et al., Dalton Trans., 2022, 51, 15996-16008, https://doi.org/10.1039/d2dt01912d.Öğe Novel and effective peripheral tetra-substituted phthalocyanines with quinazoline groups for cancer treatment: synthesis, photophysical and photochemical properties, and in-vitro studies(Elsevier Science Sa, 2024) Gulec, Ozcan; Bilgicli, Ahmet T.; Hepokur, Ceylan; Gunsel, Armagan; Arslan, Mustafa; Yarasir, M. NiluferWithin the scope of this study, starting from 3,4-dihydronaphthalen-1(2H)-one (1), 4-(2-amino-5,6-dihydrobenzo[h]quinazolin-4-yl)phenol (3) was synthesized in two stages according to literature. In the second step, 4-(4-(2-amino-5,6-dihydrobenzo[h]quinazolin-4-yl)phenoxy)phthalonitrile (4) was prepared as the starting ligand compound with the help of this substance for the first time. Then, novel metallophthalocyanine derivatives [2(3), 9(10), 16(17), 23(24)-Tetrakis[4-(2-amino-5,6-dihydrobenzo[h]quinazolin-4-yl)phenol] phthalocyaninato zinc(II) (5), copper (II) (6), cobalt (II) (7)] were synthesized in the presence of suitable metal salts. The structure of synthesized procersur and novel compounds were elucidated by convenient spectroscopic methods. The effect on solubility and aggregation behaviors substitution with 4-(2-amino-5,6-dihydrobenzo[h] quinazolin-4-yl)phenol from the peripheral position was investigated. The newly synthesized tetra -substituted phthalocyanines (5-7) show good solubility in common organic solvents. Also, they have no aggregation tendency between 1 and 10 mu M concentrations. In addition, the photophysical and photochemical properties of substituted phthalocyanines were examined. The ability to produce 1O2 of compound (5) was 0.79 in DMSO and 0.75 in THF media. Finally, the cytotoxicity effects of the synthesized phthalonitrile (4) and its metallophthalocyanines (5-7) on MCF 7, MDA-MB-231, HT -29, C6, AGS and L-929 cells were determined by XTT (2,3bis(2-methoxy-4-nitro-5-sulfophenyl)-5-[(phenylamino)carbonyl] 2H-tetrazolium hydroxide) method. The obtained data were compared with standard cell lines.Öğe Novel biologically active metallophthalocyanines as promising antioxidant-antibacterial agents: Synthesis, characterization and computational properties(Elsevier, 2020) Gunsel, Armagan; Kobyaoglu, Abdullah; Bilgicli, Ahmet T.; Tuzun, Burak; Tosun, Busra; Arabaci, Gulnur; Yarasir, M. NiluferThis study reports on the synthesis and characterization of non-peripherally tetrasubstituted zinc(II), copper(II) and cobalt(II) phthalocyanines with 4-(trifluoromethylthio)phenoxy substituents. Synthesized compounds were characterized by FT-IR, H-1 NMR, MALDI mass, elemental analysis and UV-Vis spectroscopic methods. By using some parameters obtained from quantum chemical calculations, the activity of the studied ligand (1) against metal atoms was investigated. Based on the obtained results, the NMR, IR and UV-Vis spectra of the ligand (1) in different phases were compared with experimental results. Also, theorical and experimental UV-Vis spectrum values of metallophthalocyanines (2-4) were investigated. Additionally, the possible use of all synthesized metallophthalocyanines for antioxidant and antibacterial agents were investigated. The obtained results showed that CoPc (4) had very good antioxidant activities among others. Although all of the tested metallophthalocyanines (2-4) had some antibacterial activities, ZnPc (2) had the best antibacterial effect against five different bacteria among other metallophthalocyanines tested. (C) 2019 Elsevier B.V. All rights reserved.Öğe Novel type ketone-substituted metallophthalocyanines: synthesis, spectral, structural, computational and anticancer studies(ROYAL SOC CHEMISTRY, 2017) Hepokur, Ceylan; Gunsel, Armagan; Yarasir, M. Nilufer; Bilgicli, Ahmet T.; Tuzun, Burak; Tuzun, Gamze; Yaylim, IlhanThis work reports on the synthesis and characterization of phthalocyanines (M = Cu(II) (2), Zn(II) (3) In(III) (4) and Co(II) (5)) peripherally tetra-substituted with 1-(4-hydroxyphenyl) propan-1-one. Confirmation of the synthesized phthalocyanine structures are performed with a combination of elemental analysis, FTIR, H-1-NMR, C-13-NMR, UV-vis and MALDI-MS SEM and spectral data. Their aggregation properties were examined in THF by UV-vis. Spectral and photophysical (fluorescence quantum yield) properties of complexes (2-4) were reported in THF (tetrahydrofuran). These results suggest that the metal in the core of the phthalocyanine plays an important role in the fluorescence quantum yields Phi(F) of the synthesized complexes (2-4). Also, the anticancer activities of complexes were studied on MCF-7, MG63, and L929 cell lines. Finally, all synthesized phthalocyanines were investigated by quantum chemical studies. Chemical reactivity parameters such as E-HOMO, E-LUMO, Delta E (HOMO-LUMO energy gap) were calculated by Gaussian software.Öğe Optoelectronic parameters of peripherally tetra-substituted copper(ii) phthalocyanines and fabrication of a photoconductive diode for various conditions(Royal Soc Chemistry, 2020) Gunsel, Armagan; Bilgicli, Ahmet T.; Piskin, Hasan; Tuzun, Burak; Yarasir, M. Nilufer; Gunduz, BayramIn this study, the molecular structure of 4-(4-(trifluoromethoxy)phenoxy)phthalonitrile (1) has been elucidated and its supra-molecular dynamics have been revealed by the analysis of single crystal X-ray diffraction measurements. Compound (1) and its copper(ii) phthalocyanine (2) were theoretically calculated with different basis sets. The Gibbs free energy values of copper(ii) phthalocyanine (2) were investigated. The calculated values of IR, NMR and UV-vis spectra for compound (1) and its copper(ii) phthalocyanine (2) were compared with the experimentally obtained values. The surface morphology properties of the compound (2) film for different magnifications were examined with its SEM images. We investigated the optical and optoelectronic parameters of compound (2) for different molarities. Also, we fabricated a diode based on compound (2) and examined its electronic characteristics under darkness, room light and 100 mW cm(-2). Our diode exhibits a photoconductive property.Öğe Peripheral (E)-2-[(4-hydroxybenzylidene)-3,4-dihydronaphthalen-1(2H)-one)]-coordinated phthalocyanines with improved enzyme inhibition properties and photophysicochemical behaviors(Wiley-V C H Verlag Gmbh, 2024) Gulec, Ozcan; Bilgicli, Ahmet T.; Tuzun, Burak; Taslimi, Parham; Gunsel, Armagan; Gulcin, Ilhami; Arslan, MustafaIn this study, (E)-4-{4-[(1-oxo-3,4-dihydronaphthalen-2(1H)-ylidene)methyl]phenoxy}phthalonitrile (4) and its phthalocyanine derivatives (5-8) were synthesized for the first time. Aggregation behaviors of the novel soluble phthalocyanines in organic solvents were investigated. In addition, the efficiency of O-1(2) production of (5) and ZnPc (6) was investigated. The singlet oxygen quantum yields (Phi(Delta)) for 2HPc (5) and ZnPc (6) were found to be 0.58 and 0.83, respectively. Additionally, novel phthalocyanines (5-8) were investigated for their ability to inhibit enzymes. They exhibited a highly potent inhibition effect on human carbonic anhydrase I and II (hCA I and II) and alpha-glycosidase (alpha-Gly) enzymes. K-i values are in the range of 2.60 +/- 9.87 to 11.53 +/- 6.92 mu M, 3.35 +/- 0.53 to 15.47 +/- 1.20 mu M, and 28.60 +/- 4.82 to 40.58 +/- 7.37 nM, respectively. The calculations of the studied molecule at the B3LYP, HF, and M062X levels in the 6-31G basis sets were made using the Gaussian package program. Afterward, the interactions occurring in the docking calculation against a protein that is the crystal structure of hCA I (PDB ID: 2CAB), the crystal structure of hCA II (PDB ID: 5AML), and the crystal structure of alpha-Gly (PDB ID: 1R47), were examined. Following that, Protein-Ligand Interaction Profiler (PLIP) analysis was used to look at the interactions that occurred during the docking calculation in further detail.Öğe Selective chemosensor phthalocyanines for Pd2+ ions; synthesis, characterization, quantum chemical calculation, photochemical and photophysical properties(ELSEVIER SCIENCE BV, 2019) Gunsel, Armagan; Kirbac, Erkan; Tuzun, Burak; Erdogmus, Ali; Bilgicli, Ahmet T.; Yarasir, M. NiluferIn this study, ligand (1) was prepared by a nucleophilic displacement reaction of (4-bromophenyl) methanethiol with 4-nitrophthalonitrile according to literature and its novel type peripheral substituted tetra phthalocyanines [CuPc (2), ZnPc (3) and GaPc (4)] were prepared. The phthalocyanines obtained from compound (1) were characterized by FT-IR, H-1 NMR, UV-Vis spectral data, elemental analysis, and MALDI-TOF. The novel phthalocyanines [CuPc (2), ZnPc (3) and GaPc (4)] were highly soluble in common organic solvents such as CHCl3, THF, CH2Cl2, DMSO and DMF. The effect of Pd2+ ions on the fluorescence emission and UV-Vis spectra were performed with addition of increasing amounts of Pd2+ ions. This functional phthalocyanines exhibited H-type aggregation versus Pd2+ ions due to special chemical structures, which can be used as a selective chemosensor for Pd2+ ions. Also, the molecular reactivity of the ligand (1) and related metallo phthalocyanines [CuPc (2), ZnPc (3) and GaPc (4)] were investigated and compared with the analysis of frontier molecular orbitals. In addition, photochemical and photo physical properties of these new phthalocyanines (fluorescence quantum yields, fluorescence behavior, singlet oxygen and photodegradation quantum yields) were studied in DMSO. (C) 2018 Elsevier B.V. All rights reserved.Öğe Synthesis of (4R)-2-(3-hydroxyphenyl)thiazolidine-4-carboxylic acid substituted phthalocyanines: Anticancer activity on different cancer cell lines and molecular docking studies(Wiley, 2021) Bilgicli, Ahmet T.; Genc Bilgicli, Hayriye; Hepokur, Ceylan; Tuzun, Burak; Gunsel, Armagan; Zengin, Mustafa; Yarasir, M. NiluferIn this study, firstly, (4R)-2-(3-hydroxyphenyl)thiazolidine-4-carboxylic acid (1) and (4R)-2-(3-(3,4-dicyanophenoxy)phenyl)thiazolidine-4-carboxylic acid (2) were prepared. Then, the novel type metallophthalocyanines (ZnPc (3), CuPc (4), and CoPc (5)) bearing thiazolidine groups in peripheral positions were synthesized using by compound (2). The synthesized new compounds (1-5) were characterized by the combination of standard spectroscopic methods such as FT-IR, H-1 NMR, C-13 NMR, UV-Vis spectral data, and MALDI-TOF. Aggregation behaviors of peripheral tetra-substituted metallophthalocyanines were investigated in dimethyl sulfoxide (DMSO) media. Fluorescence properties and fluorescence quantum yield of the new type zinc phthalocyanine (3) were performed in DMSO at room temperature. The anticancer activity of novel type metallophthalocyanines bearing thiazolidine groups in peripheral positions were investigated on rat glioma cancer (C6), human prostate carcinoma (DU-145), and normal human lung fibroblast (WI-38) cell lines. Finally, the biological and chemical activities of (4R)-2-(3-(3,4-dicyanophenoxy)phenyl)thiazolidine-4-carboxylic acid (2) and its novel type metallophthalocyanines (ZnPc (3), CuPc (4), and CoPc (5)) have been compared with many parameters obtained using theoretical methods that are the Gaussian software and molecular docking.Öğe Synthesis of non-peripherally tetra-substituted copper(ii) phthalocyanines: characterization, optical and surface properties, fabrication and photo-electrical properties of a photosensitive diode(Royal Soc Chemistry, 2019) Gunsel, Armagan; Bilgicli, Ahmet T.; Piskin, Hasan; Tuzun, Burak; Yarasir, M. Nilufer; Gunduz, BayramThis study describes the synthesis and characterization of a non-peripherally tetra-substituted copper(ii) phthalocyanine bearing 4-(trifluoromethoxy)phenol groups. Some spectroscopic techniques such as FT-IR, H-1-NMR, C-13-NMR, MALDI-TOF, SEM and UV-vis were used to characterize the compounds. The novel molecule of 3-(4-(trifluoromethoxy) phenoxy) phthalonitrile (1) was confirmed and its molecular structure and supra-molecular dynamics were revealed by the analysis of single crystal X-ray diffraction measurements. Ligand (1) and its copper(ii) phthalocyanine (2) were theoretically examined via HF and B3LYP, M06-2X methods by using the 3-21G, 6-31G and sdd basis sets. The calculated values of IR, NMR and UV-Vis spectra for ligand (1) and its copper(ii) phthalocyanine (2) were compared with the experimentally obtained values. The absorbance and reflectance spectra, optical band gaps, refractive indices, and the optical and electrical conductivities of compound (2) for different concentrations were investigated in detail. We fabricated a photosensitive diode and investigated its photo-electrical properties under dark and light conditions.Öğe Synthesis of tetra-substituted metallophthalocyanines: Spectral, structural, computational studies and investigation of their photophysical and photochemical properties(PERGAMON-ELSEVIER SCIENCE LTD, 2019) Guzel, Emre; Gunsel, Armagan; Tuzun, Burak; Atmaca, Goknur Yasa; Bilgicli, Ahmet T.; Erdogmus, Ali; Yarasir, M. NiluferThis work presents the synthesis of peripherally and non-peripherally tetra-substituted metallophthalocyanines (6-14) containing the 2-(3,4-dimethoxyphenyl)ethanol group. The synthesized compounds were characterized by standard spectroscopy methods. The ligands of the metallophthalocyanines were investigated by quantum chemical calculations. The quantum chemical parameters of these ligands (1 and 2) such as the HOMO, LUMO and chemical hardness were calculated by the B3lyp, HF and M062x methods. The Delta G value of the metal complexes of the ligands were calculated with the obtained results. In addition, photophysical (fluorescence quantum yields) and photochemical (singlet oxygen generation and photodegradation under light irradiation) properties of newly synthesized phthalocyanines were investigated in DMSO solutions, comparatively. (C) 2018 Elsevier Ltd. All rights reserved.Öğe Synthesis of tetra-substituted phthalocyanines bearing 2-(ethyl(m-tolyl) amino)ethanol: Computational and photophysicochemical studies(ELSEVIER SCIENCE SA, 2019) Gunsel, Armagan; Bilgicli, Ahmet T.; Tuzun, Burak; Piskin, Hasan; Atmaca, Goknur Yasa; Erdogmus, Ali; Yarasir, M. NiluferThis work presents the synthesis of 4-(2-(ethyl(m-tolyl) amino) ethoxy) phthalonitrile (1) as ligand and its peripherally tetrasubstituted metal-free (2) and metallophthalocyanines (3-5) derivatives. Synthesized compounds were characterized by standart spectroscopy methods. The molecular structure of the ligand (1) was confirmed by single-crystal X-ray diffraction experiment. The crystallographic information file (cif) was uploaded to the data center with CCDC number 1,853,485. The optimized structure of the ligand (1) and the phthalocyanines (2-5) were obtained by using different metods such as B3lyp, HF and m062x method 3-21 g, 6-31 g, sdd basis set. In b3lyp/6-31 + + g(d,p) basis set, H-1 and C-13 NMR chemical shifts, IR spectrum and UV-vis spectrum were measured in gas, chloroform and dimethylsulfoxide phase by means of the obtained optimized structure. Besides, the photophysical and photochemical properties of newly synthesized phthalocyanines (2-5) were investigated in DMSO, comparatively. Singlet oxygen quantum yields of the phthalocyanines (2-5) are ranging from 0.28 to 0.70.Öğe The new ball-type zinc phthalocyanine with S-S bridge; Synthesis, computational and photophysicochemical properties(Elsevier Science Sa, 2020) Bilgicli, Ahmet T.; Bilgicli, Hayriye Genc; Gunsel, Armagan; Piskin, Hasan; Tuzun, Burak; Yarasir, M. Nilufer; Zengin, MustafaIn this study, the starting compound 4,4'-disulfanediyldiphthalonitrile (1) and its ball-type zinc phthalocyanine (2) were synthesized and characterized by standard spectroscopic methods. The molecular structure and supramolecular dynamics of the compound (1) have been investigated by the analysis of the single crystal X-ray diffraction data. To further understand the intermolecular interactions of compound (1), the Hirshfeld surface analysis has been carried out. The compound (1) and (2) were investigated by quantum chemical calculations. Their quantum chemical parameters such as highest occupied molecular orbital (HOMO), lowest unoccupied molecular orbital (LUMO), chemical hardness were performed by B3lyp, HF, M062x method. The Delta G values of the compound (1) and (2) were calculated by using the obtained results. The calculated Infrared spectroscopy, Nuclear Magnetic Resonance, and UV-vis spectra of the compounds were investigated. In addition, photophysical (fluorescence quantum yields) and photochemical (singlet oxygen generation and photodegradation under light irradiation) properties of newly synthesized ball-type zinc phthalocyanine (2) were investigated in dimethyl sulfoxide (DMSO) solutions. We obtained very high singlet oxygen quantum yields as 0.89, suggesting its potential as photosensitizer in PDT treatment.Öğe The Water-Soluble Peripheral Substituted Phthalocyanines as Corrosion Inhibitors for Copper in 0.1 N HCl: Gravimetric, Electrochemical, SEM-EDS, and Quantum Chemical Calculations(Maik Nauka/Interperiodica/Springer, 2020) Akin, Mustafa; Gunsel, Armagan; Bilgicli, Ahmet T.; Tuzun, Burak; Arabaci, Gulnur; Saki, Neslihan; Yarasir, M. NiluferCorrosion inhibition effects of water-soluble peripheral substituted cobalt, copper and zinc metallophthalocyanines (CoPc(1), CuPc(2)and ZnPc(3)) on the copper metal in 0.1 N HCl were investigated by using gravimetric, electrochemical, SEM-EDS analysis and quantum chemical calculations. On the electrochemical investigations and gravimetric analysis the highest inhibitor efficiency was obtained with CoPc(1)at 1 x 10(-2)mol/L concentration. SEM-EDS results indicated parallel results and oxygen atom content increased in the order of ZnPc(3), CuPc(2)and CoPc(1). According to the quantum chemical calculations, following corrosion inhibition efficiency ranking was obtained: CoPc(1)> CuPc(2)> ZnPc(3).Öğe Turn-on fluorescent probe for Zn2+ ions based on thiazolidine derivative(Wiley, 2020) Bilgicli, Hayriye Genc; Bilgicli, Ahmet T.; Gunsel, Armagan; Tuzun, Burak; Ergon, Derya; Yarasir, M. Nilufer; Zengin, MustafaIn this study, simple on-off fluorescent/UV-visible (UV-Vis) probes were easily prepared using 2-(2-hydroxyphenyl)thiazolidine-4-carboxylic acid (Sen-1) and/or 2-(2-hydroxy-5-nitrophenyl)thiazolidine-4-carboxylic acid (Sen-2) for fast detection of Zn2+ ions. Their sensing properties towards common metal ions were investigated using UV-Vis and fluorescence spectroscopies. Sen-1 and Sen-2 displayed a significant change with the addition of Zn2+ ions in the UV-Vis spectra. The addition of Zn2+ ions induced a 104 nm bathochromic shift for Sen-1. The binding ratio towards Zn2+ metal ions was determined to be 1:1 by using Job plot analysis and fluorescence spectroscopy. The association constant and free energy (Delta G) of Sen-1 and Sen-2 towards Zn2+ ions were calculated by the Benesi-Hildebrand equation. The limit of detection of Sen-1 towards Zn2+ ions is 3.73 x 10(-8) M, which is about 1/100 of the value recommended by the World Health Organization for drinking water. Sen-1 was successfully applied to detect Zn2+ ions in water samples and the fluorescence test strip was prepared for visual detection of Zn2+ ions. Finally, the quantum chemical parameters of Sen-1 and Sen-2, such as highest occupied molecular orbital, lowest unoccupied molecular orbital, and chemical hardness, were investigated by the Becke, three-parameter, Lee-Yang-Parr, Hartree-Fock, and M062x methods.
