Absorption and fluorescence spectral properties of azo dyes based on 3-amido-6-hydroxy-4-methyl-2-pyridone: Solvent and substituent effects

Porobić, Slavica; Božić, Bojan Đ.; Dramićanin, Miroslav; Vitnik, Vesna; Vitnik, Željko J.; Marinović-Cincović, Milena; Mijin, Dušan Ž.

doi:10.1016/j.dyepig.2019.108139

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2020

Authors

Porobić, Slavica

Božić, Bojan Đ.

Dramićanin, Miroslav

Vitnik, Vesna

Vitnik, Željko J.
Marinović-Cincović, Milena

Mijin, Dušan Ž.

Article (Published version)

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Abstract

A series of nine 5-(4-substituted phenylazo)-3-amido-6-hydroxy-4-methyl-2-pyridones were synthesized and characterized by FT–IR, 1H and 13C NMR, UV–Vis, and PL spectroscopy. Photophysical properties of the dyes were examined in solvents of various polarities and at different pH values. The solvent effects on the absorbance and emission spectral shift were analyzed using Lippert–Mataga, Reichardt–Dimroth and Kamlet-Taft equations. Moreover, UV–Vis absorption and emission frequencies were correlated with Hammett substituent constants applying the linear free energy relationships. DFT calculations of the investigated dyes were accomplished to determine their structural and electronic properties. © 2019

Keywords:

Absorption spectra / Azo pyridone dyes / DFT / Fluorescence spectra / Solvatochromism

Source:
Dyes and Pigments, 2020, 175, 108139-

Funding / projects:

DOI: 10.1016/j.dyepig.2019.108139

ISSN: 0143-7208

WoS: 000514214600008

Scopus: 2-s2.0-85078008027

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TY  - JOUR
AU  - Porobić, Slavica
AU  - Božić, Bojan Đ.
AU  - Dramićanin, Miroslav
AU  - Vitnik, Vesna
AU  - Vitnik, Željko J.
AU  - Marinović-Cincović, Milena
AU  - Mijin, Dušan Ž.
PY  - 2020
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/8475
AB  - A series of nine 5-(4-substituted phenylazo)-3-amido-6-hydroxy-4-methyl-2-pyridones were synthesized and characterized by FT–IR, 1H and 13C NMR, UV–Vis, and PL spectroscopy. Photophysical properties of the dyes were examined in solvents of various polarities and at different pH values. The solvent effects on the absorbance and emission spectral shift were analyzed using Lippert–Mataga, Reichardt–Dimroth and Kamlet-Taft equations. Moreover, UV–Vis absorption and emission frequencies were correlated with Hammett substituent constants applying the linear free energy relationships. DFT calculations of the investigated dyes were accomplished to determine their structural and electronic properties. © 2019
T2  - Dyes and Pigments
T1  - Absorption and fluorescence spectral properties of azo dyes based on 3-amido-6-hydroxy-4-methyl-2-pyridone: Solvent and substituent effects
VL  - 175
SP  - 108139
DO  - 10.1016/j.dyepig.2019.108139
ER  -

@article{
author = "Porobić, Slavica and Božić, Bojan Đ. and Dramićanin, Miroslav and Vitnik, Vesna and Vitnik, Željko J. and Marinović-Cincović, Milena and Mijin, Dušan Ž.",
year = "2020",
abstract = "A series of nine 5-(4-substituted phenylazo)-3-amido-6-hydroxy-4-methyl-2-pyridones were synthesized and characterized by FT–IR, 1H and 13C NMR, UV–Vis, and PL spectroscopy. Photophysical properties of the dyes were examined in solvents of various polarities and at different pH values. The solvent effects on the absorbance and emission spectral shift were analyzed using Lippert–Mataga, Reichardt–Dimroth and Kamlet-Taft equations. Moreover, UV–Vis absorption and emission frequencies were correlated with Hammett substituent constants applying the linear free energy relationships. DFT calculations of the investigated dyes were accomplished to determine their structural and electronic properties. © 2019",
journal = "Dyes and Pigments",
title = "Absorption and fluorescence spectral properties of azo dyes based on 3-amido-6-hydroxy-4-methyl-2-pyridone: Solvent and substituent effects",
volume = "175",
pages = "108139",
doi = "10.1016/j.dyepig.2019.108139"
}

Porobić, S., Božić, B. Đ., Dramićanin, M., Vitnik, V., Vitnik, Ž. J., Marinović-Cincović, M.,& Mijin, D. Ž.. (2020). Absorption and fluorescence spectral properties of azo dyes based on 3-amido-6-hydroxy-4-methyl-2-pyridone: Solvent and substituent effects. in Dyes and Pigments, 175, 108139.
https://doi.org/10.1016/j.dyepig.2019.108139

Porobić S, Božić BĐ, Dramićanin M, Vitnik V, Vitnik ŽJ, Marinović-Cincović M, Mijin DŽ. Absorption and fluorescence spectral properties of azo dyes based on 3-amido-6-hydroxy-4-methyl-2-pyridone: Solvent and substituent effects. in Dyes and Pigments. 2020;175:108139.
doi:10.1016/j.dyepig.2019.108139 .

Porobić, Slavica, Božić, Bojan Đ., Dramićanin, Miroslav, Vitnik, Vesna, Vitnik, Željko J., Marinović-Cincović, Milena, Mijin, Dušan Ž., "Absorption and fluorescence spectral properties of azo dyes based on 3-amido-6-hydroxy-4-methyl-2-pyridone: Solvent and substituent effects" in Dyes and Pigments, 175 (2020):108139,
https://doi.org/10.1016/j.dyepig.2019.108139 . .