Experimental and theoretical insight into the electronic properties of 4-aryl-5-arylazo-3-cyano-6-hydroxy-2-pyridone dyes / Vesna D. Vitnik in COLORATION TECHNOLOGY, Vol. 133, N° 3 (06/2017)  

[article]  inCOLORATION TECHNOLOGY > Vol. 133, N° 3 (06/2017) . - p. 223-233 Titre : Experimental and theoretical insight into the electronic properties of 4-aryl-5-arylazo-3-cyano-6-hydroxy-2-pyridone dyes Type de document : texte imprimé Auteurs : Vesna D. Vitnik, Auteur ; Željko J. Vitnik, Auteur ; Bojan D. Bozic, Auteur ; Natasa V. Valentic, Auteur ; Sanda P. Dilber, Auteur ; Dusan Z. Mijin, Auteur ; Gordana S. Uscumlic, Auteur Année de publication : 2017 Article en page(s) : p. 223-233 Note générale : Bibliogr. Langues : Anglais (eng) Catégories : Colorants -- Analyse Colorants -- Propriétés électroniques Colorants azoïques Index. décimale : 667.3 Teinture et impression des tissus Résumé : In this paper, spectroscopic and quantum mechanical investigation of nine 4-aryl-5-arylazo-3-cyano-6-hydroxy-2-pyridone dyes was performed, and obtained density functional theory (DFT) results were compared with experimental data. The structural and spectroscopic properties of azo-2-pyridone dyes were studied by DFT using B3LYP, CAM-B3LYP, and M06-2X methods with a 6-311++G(d,p) basis set. Comparison of results reveals that the scaled theoretical vibrational frequencies of azo dyes are in good agreement with experimental data. The time-dependent DFT calculated and experimental ultraviolet-visible (UV-vis) absorption spectra are also in good agreement. The effect of electron-donating –OCH3 and electron-withdrawing –NO2 groups on the structural parameters, vibrational frequencies, UV-vis absorption, and natural bond orbital (NBO) atomic charges were thoroughly analysed. Vibrational, UV-vis, and NBO analyses confirm that investigated dyes exist in the hydrazo tautomeric form in the solid state and ethanol solution. These analyses signify the occurrence of intramolecular charge transfer in these azo-pyridone dyes. Note de contenu : - EXPERIMENTAL : General - Method of calculation - RESULTS AND DISCUSSION : Molecular geometry - Vibrational analysis - UV-vis studies and electronic properties - Frontier molecular orbital analysis - Atomic charge analysis DOI : 10.1111/cote.12271 En ligne : https://drive.google.com/file/d/1275lRats7V8B1xb9y6tmzWVCBeaDewqv/view?usp=drive [...] Format de la ressource électronique : Pdf Permalink : https://e-campus.itech.fr/pmb/opac_css/index.php?lvl=notice_display&id=28647 [article]

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Solvatochromism and quantum mechanical investigation of disazo pyridone dye / Dusan Mijin in COLORATION TECHNOLOGY, Vol. 134, N° 6 (12/2018)  

[article]  inCOLORATION TECHNOLOGY > Vol. 134, N° 6 (12/2018) . - p. 478-490 Titre : Solvatochromism and quantum mechanical investigation of disazo pyridone dye Type de document : texte imprimé Auteurs : Dusan Mijin, Auteur ; Bojan D. Bozic, Auteur ; Jelena Ladarevic, Auteur ; Luka Matovic, Auteur ; Gordana S. Uscumlic, Auteur ; Vesna D. Vitnik, Auteur ; Zeljko Vitnik, Auteur Année de publication : 2018 Article en page(s) : p. 478-490 Note générale : Bibliogr. Langues : Anglais (eng) Catégories : Colorants -- Analyse Colorants azoïques Solvatochromisme Théorie quantique Index. décimale : 667.2 Colorants et pigments Résumé : 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. Note de contenu : - EXPERIMENTAL : Materials and measurements - Synthesis - 4-methyl-2,6-dioxo-5-(2-(4-(phenyldiazenyl)phenyl)hydrazono)-1,2,5,6-tetrahydropyridine-3-carbonitrile - Method of calculation - RESULTS AND DISCUSSION : The solvent effect on absorption spectra - Correlation with multiparameter solvent polarity scales - Molecular geometry- Vibrational analysis - NMR analysis - UV-Vis studies and electronic properties - Molecular electrostatic potential DOI : 10.1111/cote.12369 En ligne : https://onlinelibrary.wiley.com/doi/epdf/10.1111/cote.12369 Format de la ressource électronique : Pdf Permalink : https://e-campus.itech.fr/pmb/opac_css/index.php?lvl=notice_display&id=31382 [article]

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Structural, spectroscopic and computational study of 5-(substituted phenylazo)-3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridones / Jelena Mirkovic in COLORATION TECHNOLOGY, Vol. 134, N° 1 (02/2018)  

[article]  inCOLORATION TECHNOLOGY > Vol. 134, N° 1 (02/2018) . - p. 33-43 Titre : Structural, spectroscopic and computational study of 5-(substituted phenylazo)-3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridones Type de document : texte imprimé Auteurs : Jelena Mirkovic, Auteur ; Bojan D. Bozic, Auteur ; Vesna D. Vitnik, Auteur ; Zeljko Vitnik, Auteur ; Jelena Rogan, Auteur ; Dejan Poleti, Auteur ; Gordana UÅ¡ćumlić, Auteur ; Dusan Mijin, Auteur Année de publication : 2018 Article en page(s) : p. 33-43 Note générale : Bibliogr. Langues : Anglais (eng) Catégories : Analyse numérique Analyse spectrale Colorants -- Analyse Colorants azoïques Cristallographie Structure cristalline (solide) Index. décimale : 667.3 Teinture et impression des tissus Résumé : Ten 5-(substituted phenylazo)-3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridones were studied (five new compounds) to provide insight into the electronic effects of diverse substituents located at different positions in their phenyl moieties. The structural features of these dyes were examined by combining experimental and theoretical approaches. The crystal structures of two derivatives were revealed by X-ray crystallography and diverse packing modes owing to different intermolecular interactions (π–π stacking and lone pair–π interactions, as well as hydrogen bonds) were found. A study on lattice energy and energy related to the molecular pairs obtained from their crystal packing was performed. The tautomerism and ionisation of the dyes in ethanol or N,N -dimethylformamide solution were rationalised in terms of diazo component substitution pattern. Note de contenu : - EXPERIMENTAL : Materials and methods - Synthesis - X-ray crystallography - Theoretical calculations - RESULTS AND DISCUSSION : Optimised geometry in vacuum - Crystal structures of 5 and 7 - Experimental vs theoretical analysis of crystal packing - Spectroscopic characterisation DOI : 10.1111/cote.12321 En ligne : https://onlinelibrary.wiley.com/doi/epdf/10.1111/cote.12321 Format de la ressource électronique : Pdf Permalink : https://e-campus.itech.fr/pmb/opac_css/index.php?lvl=notice_display&id=30125 [article]

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