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

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.

Keywords:

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

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

Publisher:

Elsevier BV

Projects:

Note:

The peer-reviewed version: http://cer.ihtm.bg.ac.rs/handle/123456789/3418

DOI: 10.1016/j.dyepig.2019.108139

ISSN: 01437208

WoS: 000514214600008

Scopus: 2-s2.0-85078008027

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TY  - JOUR
AU  - Porobić, Slavica
AU  - Božić, Bojan
AU  - Dramićanin, Miroslav
AU  - Vitnik, Vesna
AU  - Vitnik, Željko
AU  - Marinović-Cincović, Milena
AU  - Mijin, Dušan
PY  - 2020
UR  - http://cer.ihtm.bg.ac.rs/handle/123456789/3417
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.
PB  - Elsevier BV
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 and Dramićanin, Miroslav and Vitnik, Vesna and Vitnik, Željko and Marinović-Cincović, Milena and Mijin, Dušan",
year = "2020",
url = "http://cer.ihtm.bg.ac.rs/handle/123456789/3417",
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.",
publisher = "Elsevier BV",
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, Dramićanin M, Vitnik V, Vitnik Ž, Marinović-Cincović M, Mijin D. Absorption and fluorescence spectral properties of azo dyes based on 3-amido-6-hydroxy-4-methyl-2-pyridone: Solvent and substituent effects. Dyes and Pigments. 2020;175:108139

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

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