Photophysical and theoretical studies on newly synthesized N,N-diphenylamine based azo dye

Aksungur, Tuğçe; Arslan, Ömer; Seferoğlu, Nurgül; Seferoğlu, Zeynel

doi:10.1016/j.molstruc.2015.07.010

Cited by 16 publications

(5 citation statements)

References 41 publications

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“…The synthesized dye (L) exhibited decreasing in intensity of π-π * transition at pH = 10 compared to parent azo and arising a new band at 550 nm which is due to ICT from OH (donor) to pyridine ring (accepter) during the azo functional (bridge) that meaning that the electronic transition involves the overall electronic system of the azo dye (L) ligand [19]. The spectrum of hydrazone form of (L) dye at pH = 2 appears little bit red shift and increasing in intensity for ππ * transition compared to parent azo form which is in agreement with the literatures [20][21][22][23]. These dramatic changes candidates this ligand a good example on the analytical indicators of acid-base like methyl orange which is azo dye.…”

Section: Resultssupporting

confidence: 89%

Synthesis, characterization, structure determination from powder X-ray diffraction data, and biological activity of azo dye of 3-aminopyridine and its complexes of Ni(II) and Cu(II)

Mohammed¹

2021

Bull. Chem. Soc. Eth.

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In the present work azo dye ligand of 3-aminopyridine (L) and its complexes of NiII and CuII were synthesized, characterized and evaluated for antibacterial and antifungal activities in vitro. The L ligand was synthesized by reacting diazonium ion of 3-aminopyridine with 1-naphthole in presence of sodium acetate. The ligand (L) and its complexes were characterized by elemental analysis (CHN), magnetic susceptibility, molar conductivity, UV-Vis spectra, and infrared technique. The (L) azo dye exhibited high sensing for the pH changes. The color of L dye changed from red in basic medium to yellow color in acidic medium. The data of CHN, UV-Vis and magnetic susceptibility indicate that the complexes [Ni(L)2Cl2] and [Cu(L)2Cl2] are tetrahedral. The complexes of Ni(II) and Cu(II) exhibited potent activity against growth of Staphylococcus aureus and Escherichia Coli as well as against Penicillium Sp. And Aspergillus niger. Under visible irradiation (395 nm), the (L) azo dye of pyridine exhibited a significant change in the spectra under irradiation. KEY WORDS: Pyridine, Photoisomerization, Pyridylazo, Biological activity, pH sensor Bull. Chem. Soc. Ethiop. 2020, 34(3), 523-532. DOI: https://dx.doi.org/10.4314/bcse.v34i3.8

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Section: Resultssupporting

confidence: 89%

Synthesis, characterization, structure determination from powder X-ray diffraction data, and biological activity of azo dye of 3-aminopyridine and its complexes of Ni(II) and Cu(II)

Mohammed¹

2021

Bull. Chem. Soc. Eth.

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“…Template generation can be illustrated by the well‐known preparation of polypyrrole nanotubes supported by methyl orange, the method routinely reported in the literature . This dye is also currently used as an acidobasic indicator exploiting pH‐dependent azo–hydrazone tautomerism associated with intramolecular hydrogen atom transfer (Fig. ).…”

Section: Methyl Orangementioning

confidence: 99%

Strategies towards the control of one‐dimensional polypyrrole nanomorphology and conductivity

Stejskal

2018

Polymer International

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Conducting polypyrrole nanotubes rank among the most conducting polymer materials and find applications in organic electronics and energy conversion devices. They are produced by the chemical oxidation of pyrrole in globular form, which converts to nanotubes or nanofibres in the presence of suitable templates and is often accompanied by a pronounced conductivity increase. This is illustrated by the anionic dye, methyl orange, where the template formation is based on azo–hydrazone tautomerism associated with hydrogen atom transfer caused by the acidity change. In other words, the soluble salt of the dye converts to an insoluble acid, and its one‐dimensional aggregates serve as a locus for the adsorption of pyrrole oligomers. This is followed by the growth of polypyrrole chains constituting the nanotube wall. Safranin, a cationic dye, produces a template by a completely different mechanism, the oxidative generation of insoluble safranin oligomers that perform with similar results. Other mechanisms of template formation are also proposed and discussed but mainly organic dyes have a significant potential to support the one‐dimensional growth of polypyrrole. The role of surfactants that affect the morphology of templates, and subsequently also of polypyrrole, is demonstrated. © 2018 Society of Chemical Industry

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“…This leads to phenomena such as photochromism, thermochromism, ionochromism, electro-chromism, solvatochromism, vapochromism, mechanochromism, chronochromism, magnetochromism, and biochromism. [10][11][12][13] Halochromism is a subdivision of ionochromism where the dye displays visual color and fluorescence emission under the influence of OH À and H + ions by an isomerization reaction between two chemical structures possessing different properties.…”

Section: Introductionmentioning

confidence: 99%

“…Azo compounds are small in size and possess properties that can be reversibly changed by external stimuli, including light, heat, ions, electric current flow, solvents, vapors, mechanical action, time, magnetic fields, and biological environments. This leads to phenomena such as photochromism, thermochromism, ionochromism, electrochromism, solvatochromism, vapochromism, mechanochromism, chronochromism, magnetochromism, and biochromism [10–13] . Halochromism is a subdivision of ionochromism where the dye displays visual color and fluorescence emission under the influence of OH − and H + ions by an isomerization reaction between two chemical structures possessing different properties.…”

Section: Introductionmentioning

confidence: 99%

Unraveling Halochromism of Azo‐Based Sulphonamide and Its Real‐World Applications: A Combined Experimental and Theoretical Approach

Joshi,

Ganorkar

et al. 2023

ChemistrySelect

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Halochromic azo dyes have versatile applications, including sensing and anti‐counterfeiting, due to their reversible color‐changing properties. In this work we investigated the structure‐dependent halochromism of azo compound (E)‐4‐((2‐hydroxynaphthalen‐1‐yl)diazenyl)benzenesulfonamide (HDBS) and explore its potential applications using experimental and theoretical approaches. Different spectroscopic techniques confirm the structural change in the dye as a consequence of tautomerism reaction upon changing pH (7 to 13). The stable form of hydrazone is isolated and characterized. Based on the spectroscopic characterization, it is concluded that the azo form exists at pH ≤ 9, whereas the hydrazone form at highly alkaline pH. To understand the origin of the absorption peaks, the stability, and tautomerism in water, DFT and TD‐DFT calculations are performed. A reasonable agreement between the theoretical and experimental observations enabled us to unravel the structure‐dependent halochromism. Further, we have shown that HDBS‐coated paper can be a real‐time visual sensor to monitor fish freshness and for anti‐counterfeiting ink. It changes colors with pH shifts, alerts consumers about the status of food. Additionally, erasable paper strip reduces paper waste and chemical pollution. The findings presented in this work provide a promising avenue for the development of halochromic azo compounds with potential applications in sensing and anti‐counterfeiting.

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Photophysical and theoretical studies on newly synthesized N,N-diphenylamine based azo dye

Cited by 16 publications

References 41 publications

Synthesis, characterization, structure determination from powder X-ray diffraction data, and biological activity of azo dye of 3-aminopyridine and its complexes of Ni(II) and Cu(II)

Synthesis, characterization, structure determination from powder X-ray diffraction data, and biological activity of azo dye of 3-aminopyridine and its complexes of Ni(II) and Cu(II)

Strategies towards the control of one‐dimensional polypyrrole nanomorphology and conductivity

Unraveling Halochromism of Azo‐Based Sulphonamide and Its Real‐World Applications: A Combined Experimental and Theoretical Approach

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