Solvatochromism and quantum mechanical investigation of disazo pyridone dye
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2018
Authors
Mijin, Dušan
Božić, Bojan

Lađarević, Jelena

Matović, Luka

Ušćumlić, Gordana

Vitnik, Vesna

Vitnik, Željko

Article (Published version)

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Disazo pyridone dye, 4-methyl-2,6-dioxo-5-(2-(4-(phenyldiazenyl)phenyl)hydrazono)-1,2,5,6-tetrahydropyridine-3-carbonitrile, is synthesised and thoroughly characterised by a combination of experimental and computational approaches. Fourier Transform-infrared and nuclear magnetic resonance (NMR) spectra prove the existence of the hydrazone form in the solid state and in dimethyl sulphoxide, which is also supported by vibrational and NMR theoretical studies. Ultraviolet (UV) spectral properties, as well as solvatochromism in 19 solvents of different polarity, are investigated. In most of the solvents, the dye is solely present in the hydrazone form, whereas in certain solvents, an acid–base equilibrium exists. Excellent agreement between computational and experimental UV–visible data was established. Frontier Molecular Orbital analysis was performed and proved the existence of intramolecular charge transfer through the dye molecule. A molecular electrostatic potential surface was plotted... over the optimised geometry to lighten the reactivity of the investigated molecule.
Source:
Coloration Technology, 2018, 134, 6, 478-490Publisher:
- Blackwell Publishing Ltd
Funding / projects:
- Study of the Synthesis, Structure and Activity of Natural and Synthetic Organic Compounds (RS-172013)
- Rational design and synthesis of biologically active and coordination compounds and functional materials, relevant for (bio)nanotechnology (RS-172035)
- Bioinformatic promoter predictions and theoretical modeling of gene circuits in bacteria (RS-173052)
- Modeling and Numerical Simulations of Complex Many-Body Systems (RS-171017)
DOI: 10.1111/cote.12369
ISSN: 1472-3581
WoS: 000451579100007
Scopus: 2-s2.0-85052661516
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IHTMTY - JOUR AU - Mijin, Dušan AU - Božić, Bojan AU - Lađarević, Jelena AU - Matović, Luka AU - Ušćumlić, Gordana AU - Vitnik, Vesna AU - Vitnik, Željko PY - 2018 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/2412 AB - Disazo pyridone dye, 4-methyl-2,6-dioxo-5-(2-(4-(phenyldiazenyl)phenyl)hydrazono)-1,2,5,6-tetrahydropyridine-3-carbonitrile, is synthesised and thoroughly characterised by a combination of experimental and computational approaches. Fourier Transform-infrared and nuclear magnetic resonance (NMR) spectra prove the existence of the hydrazone form in the solid state and in dimethyl sulphoxide, which is also supported by vibrational and NMR theoretical studies. Ultraviolet (UV) spectral properties, as well as solvatochromism in 19 solvents of different polarity, are investigated. In most of the solvents, the dye is solely present in the hydrazone form, whereas in certain solvents, an acid–base equilibrium exists. Excellent agreement between computational and experimental UV–visible data was established. Frontier Molecular Orbital analysis was performed and proved the existence of intramolecular charge transfer through the dye molecule. A molecular electrostatic potential surface was plotted over the optimised geometry to lighten the reactivity of the investigated molecule. PB - Blackwell Publishing Ltd T2 - Coloration Technology T1 - Solvatochromism and quantum mechanical investigation of disazo pyridone dye VL - 134 IS - 6 SP - 478 EP - 490 DO - 10.1111/cote.12369 ER -
@article{ author = "Mijin, Dušan and Božić, Bojan and Lađarević, Jelena and Matović, Luka and Ušćumlić, Gordana and Vitnik, Vesna and Vitnik, Željko", year = "2018", abstract = "Disazo pyridone dye, 4-methyl-2,6-dioxo-5-(2-(4-(phenyldiazenyl)phenyl)hydrazono)-1,2,5,6-tetrahydropyridine-3-carbonitrile, is synthesised and thoroughly characterised by a combination of experimental and computational approaches. Fourier Transform-infrared and nuclear magnetic resonance (NMR) spectra prove the existence of the hydrazone form in the solid state and in dimethyl sulphoxide, which is also supported by vibrational and NMR theoretical studies. Ultraviolet (UV) spectral properties, as well as solvatochromism in 19 solvents of different polarity, are investigated. In most of the solvents, the dye is solely present in the hydrazone form, whereas in certain solvents, an acid–base equilibrium exists. Excellent agreement between computational and experimental UV–visible data was established. Frontier Molecular Orbital analysis was performed and proved the existence of intramolecular charge transfer through the dye molecule. A molecular electrostatic potential surface was plotted over the optimised geometry to lighten the reactivity of the investigated molecule.", publisher = "Blackwell Publishing Ltd", journal = "Coloration Technology", title = "Solvatochromism and quantum mechanical investigation of disazo pyridone dye", volume = "134", number = "6", pages = "478-490", doi = "10.1111/cote.12369" }
Mijin, D., Božić, B., Lađarević, J., Matović, L., Ušćumlić, G., Vitnik, V.,& Vitnik, Ž.. (2018). Solvatochromism and quantum mechanical investigation of disazo pyridone dye. in Coloration Technology Blackwell Publishing Ltd., 134(6), 478-490. https://doi.org/10.1111/cote.12369
Mijin D, Božić B, Lađarević J, Matović L, Ušćumlić G, Vitnik V, Vitnik Ž. Solvatochromism and quantum mechanical investigation of disazo pyridone dye. in Coloration Technology. 2018;134(6):478-490. doi:10.1111/cote.12369 .
Mijin, Dušan, Božić, Bojan, Lađarević, Jelena, Matović, Luka, Ušćumlić, Gordana, Vitnik, Vesna, Vitnik, Željko, "Solvatochromism and quantum mechanical investigation of disazo pyridone dye" in Coloration Technology, 134, no. 6 (2018):478-490, https://doi.org/10.1111/cote.12369 . .