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

Authorized Users Only
2020
Authors
Porobić, Slavica
Božić, Bojan Đ.
Dramićanin, Miroslav
Vitnik, Vesna
Vitnik, Željko J.
Marinović-Cincović, Milena
Mijin, Dušan Ž.
Article (Published version)
,
© 2019
Metadata
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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:
  • Materials of Reduced Dimensions for Efficient Light Harvesting and Energy conversion (RS-45020)
  • Rational design and synthesis of biologically active and coordination compounds and functional materials, relevant for (bio)nanotechnology (RS-172035)
  • Dynamics of nonlinear physicochemical and biochemical systems with modeling and predicting of their behavior under nonequilibrium conditions (RS-172015)
  • Neuroendocrine control of growth hormone secretion in humans - new challenges. Control of energy homeostasis in humans in various pathological conditions. Genetics in familial pituitary tumorigenesis. Clinical-pathological correlations in atypical pituit (RS-175033)
  • Study of the Synthesis, Structure and Activity of Natural and Synthetic Organic Compounds (RS-172013)

DOI: 10.1016/j.dyepig.2019.108139

ISSN: 0143-7208

WoS: 000514214600008

Scopus: 2-s2.0-85078008027
[ Google Scholar ]
8
7
URI
https://vinar.vin.bg.ac.rs/handle/123456789/8475
Collections
  • Radovi istraživača
Institution/Community
Vinča
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 . .

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