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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

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2020
1-s2.0-S0143720819316894-acc.pdf (1.844Mb)
Autori
Porobić, Slavica
Božić, Bojan
Dramićanin, Miroslav
Vitnik, Vesna
Vitnik, Željko
Marinović-Cincović, Milena
Mijin, Dušan
Članak u časopisu (Recenzirana verzija)
,
Elsevier
Metapodaci
Prikaz svih podataka o dokumentu
Apstrakt
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.
Ključne reči:
Azo pyridone dyes / Absorption spectra / Fluorescence spectra / Solvatochromism / DFT
Izvor:
Dyes and Pigments, 2020, 175, 108139-
Izdavač:
  • Elsevier
Finansiranje / projekti:
  • Materijali redukovane dimenzionalnosti za efikasnu apsorpciju svetlosti i konverziju energije (RS-45020)
  • Dinamika nelinearnih fizičkohemijskih i biohemijskih sistema sa modeliranjem i predviđanjem njihovih ponašanja pod neravnotežnim uslovima (RS-172015)
  • Racionalni dizajn i sinteza biološki aktivnih i koordinacionih jedinjenja i funkcionalnih materijala, relevantnih u (bio)nanotehnologiji (RS-172035)
  • Neuroendokrina kontrola sekrecije hormona rasta kod čoveka - novi izazovi. Kontrola energetske homeostaze kod čoveka u različitim patološkim stanjima. Kliničko-patološka korelacija i genetska osnova tumora hipofize i neuroendokrinih tumora (RS-175033)
  • Proučavanje sinteze, strukture i aktivnosti organskih jedinjenja prirodnog i sintetskog porekla (RS-172013)
Napomena:
  • 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
[ Google Scholar ]
17
7
URI
https://cer.ihtm.bg.ac.rs/handle/123456789/3418
Kolekcije
  • Radovi istraživača / Researchers' publications
Institucija/grupa
IHTM
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  - 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 . .

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