Solvatochromism and quantum mechanical investigation of disazo pyridone dye
Само за регистроване кориснике
2018
Аутори
Mijin, DušanBožić, Bojan
Lađarević, Jelena
Matović, Luka
Ušćumlić, Gordana
Vitnik, Vesna
Vitnik, Željko
Чланак у часопису (Објављена верзија)
Метаподаци
Приказ свих података о документуАпстракт
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.
Извор:
Coloration Technology, 2018, 134, 6, 478-490Издавач:
- Blackwell Publishing Ltd
Финансирање / пројекти:
- Проучавање синтезе, структуре и активности органских једињења природног и синтетског порекла (RS-MESTD-Basic Research (BR or ON)-172013)
- Рационални дизајн и синтеза биолошки активних и координационих једињења и функционалних материјала, релевантних у (био)нанотехнологији (RS-MESTD-Basic Research (BR or ON)-172035)
- Биоинформатички методи за детекцију промотера и теоријско моделовање генских кола (RS-MESTD-Basic Research (BR or ON)-173052)
- Моделирање и нумеричке симулације сложених вишечестичних система (RS-MESTD-Basic Research (BR or ON)-171017)
DOI: 10.1111/cote.12369
ISSN: 1472-3581
WoS: 000451579100007
Scopus: 2-s2.0-85052661516
Институција/група
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 . .