Absorption and fluorescence spectral properties of azo dyes based on 3-amido-6-hydroxy-4-methyl-2-pyridone: Solvent and substituent effects
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2020
Authors
Porobić, SlavicaBožić, Bojan Đ.
Dramićanin, Miroslav
Vitnik, Vesna
Vitnik, Željko J.
Marinović-Cincović, Milena
Mijin, Dušan Ž.
Article (Published version)
,
© 2019
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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 / SolvatochromismSource:
Dyes and Pigments, 2020, 175, 108139-Funding / projects:
- Materials of Reduced Dimensions for Efficient Light Harvesting and Energy conversion (RS-MESTD-Integrated and Interdisciplinary Research (IIR or III)-45020)
- Rational design and synthesis of biologically active and coordination compounds and functional materials, relevant for (bio)nanotechnology (RS-MESTD-Basic Research (BR or ON)-172035)
- Dynamics of nonlinear physicochemical and biochemical systems with modeling and predicting of their behavior under nonequilibrium conditions (RS-MESTD-Basic Research (BR or ON)-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-MESTD-Basic Research (BR or ON)-175033)
- Study of the Synthesis, Structure and Activity of Natural and Synthetic Organic Compounds (RS-MESTD-Basic Research (BR or ON)-172013)
DOI: 10.1016/j.dyepig.2019.108139
ISSN: 0143-7208
WoS: 000514214600008
Scopus: 2-s2.0-85078008027
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VinčaTY - 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 . .