Structural and Spectral Investigation of a Series of Flavanone Derivatives

Sykuła, Anna; Kowalska-Baron, Agnieszka; Gałęcki, Krystian; Błazińska, Paulina; Łodyga-Chruścińska, Elżbieta

doi:10.3390/molecules26051298

Cited by 6 publications

(3 citation statements)

References 44 publications

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“…HABH synthesis is presented in Figure 1. The ligand 2-amino-benzoic acid [5,7-dihydroxy-2-(3-hydroxy-4-methoxy-phenyl)chroman-4-ylidene]-hydrazide (HABH) was prepared according to the literature procedure [22,23] with some modifications. The synthesis product was filtered off, washed with ethanol and methanol and then dried to give a solid ligand.…”

Section: Characterization Of Habhmentioning

confidence: 99%

From the Physicochemical Characteristic of Novel Hesperetin Hydrazone to Its In Vitro Antimicrobial Aspects

et al. 2022

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Microorganisms are able to give rise to biofilm formation on food matrixes and along food industry infrastructures or medical equipment. This growth may be reduced by the application of molecules preventing bacterial adhesion on these surfaces. A new Schiff base ligand, derivative of hesperetin, HABH (2-amino-N′-(2,3-dihydro-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)chromen-4-ylidene)benzohydrazide), and its copper complex, CuHABH [CuLH2(OAc)], were designed, synthesized and analyzed in terms of their structure and physicochemical properties, and tested as antibacterial agents. Their structures both in a solid state and in solution were established using several methods: FT-IR, 1H NMR, 13C NMR, UV-Vis, FAB MS, EPR, ESI-MS and potentiometry. Coordination binding of the copper(II) complex dominating at the physiological pH region in the solution was found to be the same as that detected in the solid state. Furthermore, the interaction between the HABH and CuHABH with calf-thymus DNA (CT-DNA) were investigated. These interactions were tracked by UV-Vis, CD (circular dichroism) and spectrofluorimetry. The results indicate a stronger interaction of the CuHABH with the CT-DNA than the HABH. It can be assumed that the nature of the interactions is of the intercalating type, but in the high concentration range, the complex can bind to the DNA externally to phosphate residues or to a minor/major groove. The prepared compounds possess antibacterial and antibiofilm activities against Gram-positive and Gram-negative bacteria. Their antagonistic activity depends on the factor-strain test system. The glass was selected as a model surface for the experiments on antibiofilm activity. The adhesion of bacterial cells to the glass surface in the presence of the compounds was traced by luminometry and the best antiadhesive action against both bacterial strains was detected for the CuHABH complex. This molecule may play a crucial role in disrupting exopolymers (DNA/proteins) in biofilm formation and can be used to prevent bacterial adhesion especially on glass equipment.

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Section: Characterization Of Habhmentioning

confidence: 99%

From the Physicochemical Characteristic of Novel Hesperetin Hydrazone to Its In Vitro Antimicrobial Aspects

et al. 2022

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“…One of the principal goals of theoretical chemists is to develop new and useful rules and theories to explain the reactivity properties and to predict the directions and mechanisms of chemical reactions [ 1 – 10 ]. Density functional theory (DFT) that was revealed in accordance with this goal uses the electron density to identify the reactivity or stability [ 11 – 17 ].…”

Section: Introductionmentioning

confidence: 99%

Theoretical analysis of OLED performances of some aromatic nitrogen-containing ligands

ELİK

2023

Turkish Journal of Chemistry

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It is well-known that tris(8-hydroxyquinoline) aluminum (Alq3) complex and N,N′diphenyl-N,N′-bis(3-methylphenyl)-1,1′-diphenyl-4,4′-diamine compound (TPD) are widely used as electron transfer material (ETL) and hole transfer material (HTL) in organic light emitting diode (OLED) structure, respectively. Considering the reference materials, in the present work, the OLED performances of some cyclic aromatic structures such as 4,4′azopyridine [AZPY], 4,4′-bipyridine [BIPY], 1,2-bis[4′-(4-methylphenyl)2,2′:6′2″-terpyridin6-yl]ethyne (BISTERPY), 5,5′-diamino-2,2′-bipyridine (DABP), dipyrido[3,2-a:2′,3′c]phenazine (DPP), 4,7-phenanthroline (PHEN) including nitrogen atom have been theoretically analyzed. It is important to note that B3LYP/6-31G(d) and B3LYP/TZP levels of the theory were taken into account for the calculations about monomeric and dimeric structures, respectively. Additionally, the calculations of the mentioned monomeric form were performed at B3LYP-D3/6-31G, CAM-B3LYP/6-31G and ωB97X-D/6-31G(d) levels. For a detailed theoretical analysis, the reorganization energies (λe and λh), adiabatic and vertical ionization potentials and electron affinities, the effective transfer integrals (Ve and Vh), and the charge transfer rates (We and Wh) of all compounds were computed by means of computational chemistry tools. In the light of calculated parameters, it is determined that these mentioned aromatic cyclic structures will be used in which layers of OLED structure. The results obtained in this study will be helpful in the design and applications of new molecules as OLED materials in the future.

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“…One of the principal goals of theoretical chemists is to develop new and useful rules and theories to explain the reactivity properties and to predict the directions and mechanisms of chemical reactions [1][2][3][4][5][6][7][8][9][10]. Density Functional Theory (DFT) that was revealed in accordance with this goal uses the electron density to identify the reactivity or stability [11][12][13][14][15][16][17].…”

Section: Introductionmentioning

confidence: 99%

Theoretical Analysis of OLED Performances of Some Aromatic Nitrogen-Containing Ligands

Elik

2021

Preprint

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It is well-known that tris(8‐hydroxyquinoline) aluminum (Alq3) complex and N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'-diphenyl-4,4'-diamine compound (TPD) are widely used as electron transfer material (ETL) and hole transfer material (HTL) in organic light emitting diode (OLED) structure, respectively. Considering the reference materials, in the present work, the OLED performances of some cyclic aromatic structures such as 4,4ꞌ-azopyridine [AZPY], 4,4ꞌ-bipyridine [BIPY], 1,2-bis[4ꞌ-(4-methylphenyl)2,2ꞌ:6ꞌ2ꞌꞌ-terpyridin-6-yl]ethyne (BISTERPY), 5,5ꞌ-diamino-2,2ꞌ-bipyridine (DABP), dipyrido[3,2-a:2ꞌ,3ꞌ-c]phenazine (DPP), 4,7-phenanthroline (PHEN) including nitrogen atom have been theoretically analyzed. It is important to note that B3LYP/6-31G(d) and B3LYP/TZP levels of the theory were taken into account for the calculations about monomeric and dimeric structures, respectively. For a detailed theoretical analysis, the reorganization energies (λe and λh), adiabatic and vertical ionization potentials and electron affinities, the effective transfer integrals (Ve and Vh), and the charge transfer rates (We and Wh) of all compounds were computed by means of computational chemistry tools. In the light of calculated parameters, it is determined that these mentioned aromatic cyclic structures will be used in which layers of OLED structure. The results obtained in this study will be helpful in the design and applications of new molecules as OLED materials in the future.

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Structural and Spectral Investigation of a Series of Flavanone Derivatives

Cited by 6 publications

References 44 publications

From the Physicochemical Characteristic of Novel Hesperetin Hydrazone to Its In Vitro Antimicrobial Aspects

From the Physicochemical Characteristic of Novel Hesperetin Hydrazone to Its In Vitro Antimicrobial Aspects

Theoretical analysis of OLED performances of some aromatic nitrogen-containing ligands

Theoretical Analysis of OLED Performances of Some Aromatic Nitrogen-Containing Ligands

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