Absorption and fluorescence spectral properties of azo dyes based on 3-amido-6-hydroxy-4-methyl-2-pyridone: Solvent and substituent effects
Authors
Porobić, Slavica
Božić, Bojan

Dramićanin, Miroslav

Vitnik, Vesna

Vitnik, Željko

Marinović-Cincović, Milena

Mijin, Dušan

Article (Accepted Version)

Elsevier
Metadata
Show full item recordAbstract
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 / DFTSource:
Dyes and Pigments, 2020, 175, 108139-Publisher:
- Elsevier
Funding / projects:
- Materials of Reduced Dimensions for Efficient Light Harvesting and Energy conversion (RS-45020)
- Dynamics of nonlinear physicochemical and biochemical systems with modeling and predicting of their behavior under nonequilibrium conditions (RS-172015)
- Rational design and synthesis of biologically active and coordination compounds and functional materials, relevant for (bio)nanotechnology (RS-172035)
- 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)
Note:
- This is the pper-reviewed version of the article: Dyes and Pigments, 2020, 175, 108139, doi: https://doi.org/10.1016/j.dyepig.2019.108139
- The published version: http://cer.ihtm.bg.ac.rs/handle/123456789/3417
DOI: 10.1016/j.dyepig.2019.108139
ISSN: 0143-7208
WoS: 000514214600008
Scopus: 2-s2.0-85078008027
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Institution/Community
IHTMTY - 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 - https://cer.ihtm.bg.ac.rs/handle/123456789/3418 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 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", 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", 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.. (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 Elsevier., 175, 108139. https://doi.org/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. in Dyes and Pigments. 2020;175:108139. doi: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" in Dyes and Pigments, 175 (2020):108139, https://doi.org/10.1016/j.dyepig.2019.108139 . .