Vibrational and electronic investigations, NLO, FMO analysis on a hetarylazoindole disperse dye by density functional theory

Çatıkkaş, Berna; Aktan, Ebru; Yalçın, Ergin

doi:10.1016/j.molstruc.2016.03.074

Cited by 12 publications

(4 citation statements)

References 39 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Azo dyes are of potential biological activities such as antifungal [11][12][13][14][15][16][17], antimycobacterial [18], antibacterial [19], anticancer-chemotherapy [20][21][22], anti-HIV [23][24][25][26][27][28], DNA-cleavage [29] and in the textile, food and cosmetics industry [30][31][32]. Azo dyes are interesting compounds that can be used in many applications due to their colors and different properties [33][34].…”

Section: Introduction (Gi̇ri̇ş)mentioning

confidence: 99%

Structure and Spectroscopic Studies of Bis Azo Compounds with S/SO2 Bridges and Containing Cyclic-1,3-Dicarbonyl Groups

ERTEN,

ÇOLAK

2023

Gazi Üniversitesi Fen Bilimleri Dergisi Part C: Tasarım Ve Teknoloji

View full text Add to dashboard Cite

A series of new bis azo dyes were synthesized starting from aromatic diamine with S/SO2 bridges and cyclic-1,3-dicarbonyl groups; contain active methylene group, namely; 3,3-dimethyl-1,5-cyclohexadione (dimedone), 1,3-cyclohexadione and 2,2-dimethyl-1,3-dioxane-4,6-dione to give 1-6. Whether the reaction is complete and the purity of the compounds were checked with TLC. The structure of the newly synthezed compounds was investigated by using, FT-IR, 1HNMR, LC–MS/MS and UV–Visible spectrophotometric methods, CH3OH was used in the LC-MS/MS experiments, and the molecular masses of the compounds were seen as M and M+1 protonated in the spectrum. In the UV-Vis spectra of these compounds, the solvent effect by using different solvents and also the acid-base effect by adding HCl or KOH to the medium were investigated. The tautomeric equilibrium forms (enol-imine O-H….N, keto-amine O….H-N forms) of the compounds were investigated according to the electronic spectrum recorded in chloroform, dimethylformamide (DMF), acetic acid, and methanol solvents. The results of the UV-visible and 1H-NMR spectra indicated that the compounds in chloroform, dimethylformamide (DMF), acetic acid and methanol were found in the hydrazo tautomer (keto-amine O….H-N forms) of the proposed tautomeric forms.

show abstract

Section: Introduction (Gi̇ri̇ş)mentioning

confidence: 99%

Structure and Spectroscopic Studies of Bis Azo Compounds with S/SO2 Bridges and Containing Cyclic-1,3-Dicarbonyl Groups

ERTEN,

ÇOLAK

2023

Gazi Üniversitesi Fen Bilimleri Dergisi Part C: Tasarım Ve Teknoloji

View full text Add to dashboard Cite

show abstract

“…[59,60] Similarly, anthraquinone-based azo dyes also show improved NLO properties. [61] Standard approaches for example, "Electric Field Induced Second Harmonic Generation (EFISHG), Hyper-Rayleigh scattering (HRS), [62,63] solvatochromic [56,[64][65][66] and Z-scan method, [52,61,67,68,69] can be used to determine NLO characteristics of molecules. [70,71] The simplicity and sensitivity of the Z-scan method make it more versatile for measuring " third-order nonlinear optical susceptibility(χ 3 ), nonlinear refractive index (� 2 ), optical limiting (OL) values, nonlinear absorption coefficients(β)".…”

Section: Introductionmentioning

confidence: 99%

NLOphoric Azo Dyes Studied Using Z‐Scan

Ramugade

Ghanavatkar

Mathew³

et al. 2022

ChemistrySelect

View full text Add to dashboard Cite

Disperse Red 343((E)‐N‐(2‐((2,6‐dicyano‐4‐methylphenyl) diazenyl) ‐ 5 ‐ (diethylamino) phenyl)methanesulfonamide,1 a), Disperse Red177((E) ‐ methyl3‐((2‐cyanoethyl)(4‐((6‐nitrobenzo [d]thiazol‐2‐yl)diazenyl) phenyl) amino) propanoate,1 b), Disperse Blue 165((E) ‐ N ‐ (2 ‐ ((2,6 ‐ dicyano ‐ 4 ‐nitrophenyl)diazenyl)‐5‐ (diethylamino) phenyl) acetamide, 1 c), Disperse Blue 165.1((E) ‐ N ‐ (5 ‐ (benzyl (ethyl) amino) ‐ 2 ‐ ((2‐cyano ‐ 4,6‐dinitrophenyl) diazenyl) phenyl) acetamide, 1 d), Disperse Blue 366 ((E) ‐ 2 ‐ ((4‐ (diethylamino) ‐ 2 ‐ methylphenyl) diazenyl) ‐ 5 nitroisophthalonitrile, 1 e), and Disperse Blue 148((E) ‐ methyl 3‐(ethyl (4 ‐ ((5 ‐ nitrobenzo [c]I sothiazol‐3‐yl) diazenyl) phenyl) amino) propanoate, 1 f) were examined in solvents for their non‐linear optical properties using Z‐scan technique. Because of their CT characteristics, they have shown positive solvatochromism. As observed in nonpolar solvents, the ground states are more stable than their excited states. Changes in solvating the low‐lying ground state and the state above generate the bathochromic shift in vertical excitation. The dye 1 b produces the maximum x3(7.95×10-134pte.s.u.) due to strong NO2 donor‐ п‐ acceptors systems in DMSO. We found a positive nonlinear refractive index (η2) in both series using the closed aperture (valley‐peak) compared to the other five disperse dyes. Dye 1 c (with two cyano groups) has a ′larger nonlinear susceptibility (χ3)′ in DMSO than in the other two solvents (acetone, ethanol). Dye 1 a–1 f showed LDT (9.109, 6.553,4.641,6.44) W/m2 respectively. The “nonlinear absorptive coefficient (β), nonlinear refractive index (η2), third‐order nonlinear optical susceptibility χ(3) and optical limiting (OL)” of acetone, ethanol, and DMSO are determined using the Z‐scan technique, and the results are significantly better than earlier known dyes.

show abstract

“…In the meantime, they are also known for their absorption properties, biological activities, and NLO (nonlinear optic) properties. Investigation of frontier molecule optical studies of the azo dyes were reported previously [1] …”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of Azo Dye Complexes as Potential Inhibitors of Acetylcholinesterase, Butyrylcholinesterase, and Glutathione S‐Transferase

et al. 2022

View full text Add to dashboard Cite

In this study, several metal(II) complexes (Fe, Co, Zn, and Ru) of an azo dye ligand (ADL) that, apart from pyrazole ring (PR), include anisole having (−OCH3) group at the m‐substitue of the phenyl (L: (E)‐4‐((3‐methoxyphenyl)diazenyl)‐3‐methyl‐1H‐pyrazol‐5‐amine) were prepared, characterized, and the biological activity studies were carried out. The structures of complexes were identified by elemental analysis, FTIR, UV‐vis, mass spectra (Fe(II) and Co(II)), 1H‐13C NMR spectra, and TGA‐DTA. The azo ligand and its metal complexes were evaluated for their biological properties according to the enzyme inhibitory activities. The lowest Ki values of Co(II) complex against all three GST (19.48±2.17 μM), AChE (22.14±3.74 μM), and BChE (26.39±3.19 μM) enzymes were verified as the most effective enzyme inhibition. The biological activity results suggest that the obtained complexes have good potentials to be used in further analyses to explore new pharmaceutical agents.

show abstract

Vibrational and electronic investigations, NLO, FMO analysis on a hetarylazoindole disperse dye by density functional theory

Cited by 12 publications

References 39 publications

Structure and Spectroscopic Studies of Bis Azo Compounds with S/SO2 Bridges and Containing Cyclic-1,3-Dicarbonyl Groups

Structure and Spectroscopic Studies of Bis Azo Compounds with S/SO2 Bridges and Containing Cyclic-1,3-Dicarbonyl Groups

NLOphoric Azo Dyes Studied Using Z‐Scan

Synthesis and Characterization of Azo Dye Complexes as Potential Inhibitors of Acetylcholinesterase, Butyrylcholinesterase, and Glutathione S‐Transferase

Contact Info

Product

Resources

About