Synthesis, Characterisation and DFT Calculations of Azo-Imine Dyes

Sevil Özkınalı; Muhammet Serdar Çavuş; Büşra Umur Sakin

doi:10.18596/jotcsa.346278

Araştırma Makalesi

Synthesis, Characterisation and DFT Calculations of Azo-Imine Dyes

Yıl 2018, Cilt: 5 Sayı: 1, 159 - 178, 01.09.2017

Sevil Özkınalı Muhammet Serdar Çavuş Büşra Umur Sakin

https://doi.org/10.18596/jotcsa.346278

Cited By: 3

Öz

In this study, azo dyes containing an imine group were synthesised by coupling
p-hydroxybenzylidene aniline with the diazonium salts of p-toluidine,
4-aminophenol, aniline, p-chloroaniline,
p-fluoroaniline and p-nitroaniline.
The compounds were characterised by melting point, elemental, UV-Vis and IR analyses as well as
¹H-NMR and ¹³C-NMR spectroscopies. Moreover, the
experimental data were supplemented with density functional theory (DFT) calculations. The experimental data on FT-IR and UV–Vis spectra of
the compounds were compared with theoretical results. The DFT calculations were performed to obtain the ground
state geometries of the compounds using the B3LYP hybrid functional level with 6-311++g(2d,2p)
basis set. Frontier molecular orbital energies, band gap energies and some chemical reactivity
parameters, such as chemical hardness and electronegativity, were calculated and compared with experimental values. A significant correlation was observed between the
dipole moment and polarities of the solvents and the absorption wavelength of
the compounds.

Anahtar Kelimeler

Azo-imine, Schiff Bases, DFT

Kaynakça

Umape P.G, Patil V.S, Padalkar V.S, Phatangare K.R, Gupta V.D, Thate A.B, Sekar N, Synthesis and characterization of novel yellow azo dyes from 2-morpholin-4-yl-1,3-thiazol-(5H)-one and study of their azo-hydrazone tautomerism. Dyes and Pigments. 2013;99: 291-298.
Gür M., Kocaokutgen H., M. Taş, Synthesis, spectral and thermal characterissation of some azo-ester derivatives containing a 4-acryloyloxy group, Dyes and Pigments, 2007, 72, 101-108.
Al-Hamdani A.A.S, Balkhi A.M, Falah A, Shaker S.A, Synthesis and investigation of thermal properties of vanadyl complexes with azo-containing Schiff-base dyes, Journal of Saudi Chemical Society, 2016; 20: 487-501
Bitmez Ş, Sayin K, Avar B, Köse M, Karayıldız A, Kurtoğlu M, Preparation, spectral, X-ray powder diffraction and computational studies and genotoxic properties of new azo–azomethine metal chelates, Journal of Molecular Structure. 2014:1076; 213–226
Eren T, Köse M, Kurtoğlu N, Ceyhan G, McKee V, Kurtoğlu M, An azo-azomethine ligand and its copper(II) complex: Synthesis, X-ray crystal structure, spectral, thermal, electrochemical and photoluminescence properties. Inorganica Chimica Acta 2015; 430: 268–279
Köse M, Kurtoğlu N, Gümüşsu Ö, Tutak M, McKee V, Karakaş D, Kurtoğlu M, Synthesis, characterization and antimicrobial studies of 2-{(E)-[(2-hydroxy-5-methylphenyl)imino]methyl}-4-[(E)-phenyldiazenyl] phenol as a novel azo-azomethine dye. Journal of Molecular Structure. 2013; 1053: 89–99 7. Kantar C, Mavi, V, Baltas N¸ İslamoğlu F, Şaşmaz S, Novel zinc(II)phthalocyanines bearing azo-containing schiff base: Determination of pKa values, absorption, emission, enzyme inhibition and photochemical properties. Journal of Molecular Structure. 2016; 1122: 88-99
Purtas F, Sayin K, Ceyhan G, Kose M, Kurtoglu M, New fluorescent azo-Schiff base Cu(II) and Zn(II) metal chelates; spectral, structural, electrochemical, photoluminescence and computational studies. Journal of Molecular Structure. 2017; 1137: 461-475.
Alaghaz A.M.A, Zayed M. E, Alharbi S. A, Synthesis, spectral characterization, molecular modeling and antimicrobial studies of tridentate azo-dye Schiff base metal complexes. Journal of Molecular Structure. 2015; 1084: 36–45
Zakerhamidi M.S, Nejati K, Sorkhabi S.G, Saati M, Substituent and solvent effects on the spectroscopic properties and dipole moments of hydroxyl benzaldehyde azo dye and related Schiff bases. Journal of Molecular Liquids. 2013; 180: 225–234
Anitha C, Sheela C.D, Tharmaraj P, Sumathi S, Spectroscopic studies and biological evaluation of some transition metal complexes of azo Schiff-base ligand derived from (1-phenyl-2,3-dimethyl-4-aminopyrazol-5-one) and 5-((4-chlorophenyl)diazenyl)-2-hydroxybenzaldehyde. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. 2012; 96: 493–500
Nazır H, Yıldız M, Yılmaz H, Tahir M.N, Ülkü D, Intramolecular hydrogen bonding and tautomerism in Schiff bases. Structure of N-(2-pyridil)-2-oxo-1-naphthlidenemethylamine. Journal of Molecular Structure. 2000; 524: 241-250
Pal M.K, Kushwah N, Wadawale AP, Manna D, Sudarsan V, Ghanty T.K, Jain V.K, Synthesis, characterization, photoluminescence and computational studies of mono- and diorgano-gallium complexes containing azo linked salicylaldimine Schiff bases. Journal of Organometallic Chemistry. 2015; 776: 98-106
Nagy P.I, Fabian W.M.F, Theoretical Study of the Enol Imine-Enaminone Tautomeric Equilibrium in Organic Solvents. J. Phys. Chem. B. 2006; 110: 25026-25032
Alaghaz A.M.A, Zayed M. E, Alharbi S. A, Synthesis, spectral characterization, molecular modeling and antimicrobial studies of tridentate azo-dye Schiff base metal complexes. Journal of Molecular Structure. 2015; 1084: 36–45
Qian H.F, Tao T, Feng Y.N, Wang Y.G, Huang W, Crystal structures, solvatochromisms and DFT computations of three disperse azo dyes having the same azobenzene skeleton. Journal of Molecular Structure. 2016; 1123: 305-310
Atay Ç.K, Gökalp M, Kart S.Ö, Tilki T, Mono azo dyes derived from 5-nitroanthranilic acid: Synthesis, absorption properties and DFT calculations. Journal of Molecular Structure. 2017; 1141: 237-244.
Sreenath M.C, Mathew S, Joe H.I, Rastogi V.K, Z-scan measurements of the third-order optical nonlinearities and vibrational spectral studies by DFT computations on azo dye 1-(2-Methylphenylazo)-2-napthol. Optics and Laser Technology. 2017; 97: 390–399.
Deshmukh M.S, Sekar N, A combined experimental and TD-DFT investigation of three disperse azo dyes having the nitroterephthalate skeleton. Dyes and Pigments. 2014; 103: 25-33
Turkten N, Cinar Z, Photocatalytic decolorization of azo dyes on TiO2: Prediction ofmechanism via conceptual DFT. Catalysis Today. 2017; 287: 169–175
Miraftab R, Ramezanzadeh B, Bahlakeh G, Mahdavian M, An advanced approach for fabricating a reduced graphene oxide-AZO dye/polyurethane composite with enhanced ultraviolet (UV) shielding. Chemical Engineering Journal. 2017; 321: 159–174
Erfantalab M, Khanmohammadi H, New 1,2,4-triazole-based azo–azomethine dye. Part III: Synthesis, characterization, thermal property, spectrophotometric and computational studies properties: Experimental and first-principles QM modeling. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. 2014; 125: 345–352
Gür M, Muğlu H, Çavus M.S, Güder A, Sayıner H.S, Kandemirli F, Synthesis, characterization, quantum chemical calculations and evaluation of antioxidant properties of 1,3,4-thiadiazole derivatives including 2- and 3-methoxy cinnamic acids. Journal of Molecular Structure. 2017; 1134: 40-50
Kohn W, Sham L.J, Self-consistent equations including exchange and correlation effects. Phys. Rev. 1965; 140: A1133.
Gaussian 09, Revision B.01, Frisch M. J, Trucks G. W, Schlegel H. B, Scuseria G. E, Robb M. A, Cheeseman J. R, Scalmani G., Barone V, Mennucci B, Petersson G. A, Nakatsuji H, Caricato M, Li X, Hratchian H. P, Izmaylov A. F, Bloino J, Zheng G, Sonnenberg J. L, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery J. A, Peralta J. E, Ogliaro F, Bearpark M, Heyd J. J, Brothers E, Kudin K. N, Staroverov V. N, Keith T, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant J. C, Iyengar S. S, Tomasi J, Cossi M, Rega N, Millam J. M, Klene M, Knox J. E, Cross J. B, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann R. E, Yazyev O, Austin A. J, Cammi R, Pomelli C, Ochterski J. W, Martin R. L, Morokuma K, Zakrzewski V. G, Voth G. A, Salvador P, Dannenberg J. J, Dapprich S, Daniels A. D, Farkas O, Foresman J. B, Ortiz J. V, Cioslowski J, Fox D. J, Gaussian, Inc., Wallingford CT, 2010.
Becke AD, A new mixing of HartreeeFock and local density-functional theories. J Chem Phys. 1993; 98:1372-7.
Lee C, Yang W, Parr RG. Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys Rev B 1988; 37: 785-9.
Cossi M, Barone V, Cammi R, Tomasi J., Ab initio study of solvated molecules: a new implementation of the polarizable continuum model, Chem. Phys. Lett. 1996;255: 327-335.

Yıl 2018, Cilt: 5 Sayı: 1, 159 - 178, 01.09.2017

Sevil Özkınalı Muhammet Serdar Çavuş Büşra Umur Sakin

https://doi.org/10.18596/jotcsa.346278

Cited By: 3

Öz

Kaynakça

Umape P.G, Patil V.S, Padalkar V.S, Phatangare K.R, Gupta V.D, Thate A.B, Sekar N, Synthesis and characterization of novel yellow azo dyes from 2-morpholin-4-yl-1,3-thiazol-(5H)-one and study of their azo-hydrazone tautomerism. Dyes and Pigments. 2013;99: 291-298.
Gür M., Kocaokutgen H., M. Taş, Synthesis, spectral and thermal characterissation of some azo-ester derivatives containing a 4-acryloyloxy group, Dyes and Pigments, 2007, 72, 101-108.
Al-Hamdani A.A.S, Balkhi A.M, Falah A, Shaker S.A, Synthesis and investigation of thermal properties of vanadyl complexes with azo-containing Schiff-base dyes, Journal of Saudi Chemical Society, 2016; 20: 487-501
Bitmez Ş, Sayin K, Avar B, Köse M, Karayıldız A, Kurtoğlu M, Preparation, spectral, X-ray powder diffraction and computational studies and genotoxic properties of new azo–azomethine metal chelates, Journal of Molecular Structure. 2014:1076; 213–226
Eren T, Köse M, Kurtoğlu N, Ceyhan G, McKee V, Kurtoğlu M, An azo-azomethine ligand and its copper(II) complex: Synthesis, X-ray crystal structure, spectral, thermal, electrochemical and photoluminescence properties. Inorganica Chimica Acta 2015; 430: 268–279
Köse M, Kurtoğlu N, Gümüşsu Ö, Tutak M, McKee V, Karakaş D, Kurtoğlu M, Synthesis, characterization and antimicrobial studies of 2-{(E)-[(2-hydroxy-5-methylphenyl)imino]methyl}-4-[(E)-phenyldiazenyl] phenol as a novel azo-azomethine dye. Journal of Molecular Structure. 2013; 1053: 89–99 7. Kantar C, Mavi, V, Baltas N¸ İslamoğlu F, Şaşmaz S, Novel zinc(II)phthalocyanines bearing azo-containing schiff base: Determination of pKa values, absorption, emission, enzyme inhibition and photochemical properties. Journal of Molecular Structure. 2016; 1122: 88-99
Purtas F, Sayin K, Ceyhan G, Kose M, Kurtoglu M, New fluorescent azo-Schiff base Cu(II) and Zn(II) metal chelates; spectral, structural, electrochemical, photoluminescence and computational studies. Journal of Molecular Structure. 2017; 1137: 461-475.
Alaghaz A.M.A, Zayed M. E, Alharbi S. A, Synthesis, spectral characterization, molecular modeling and antimicrobial studies of tridentate azo-dye Schiff base metal complexes. Journal of Molecular Structure. 2015; 1084: 36–45
Zakerhamidi M.S, Nejati K, Sorkhabi S.G, Saati M, Substituent and solvent effects on the spectroscopic properties and dipole moments of hydroxyl benzaldehyde azo dye and related Schiff bases. Journal of Molecular Liquids. 2013; 180: 225–234
Anitha C, Sheela C.D, Tharmaraj P, Sumathi S, Spectroscopic studies and biological evaluation of some transition metal complexes of azo Schiff-base ligand derived from (1-phenyl-2,3-dimethyl-4-aminopyrazol-5-one) and 5-((4-chlorophenyl)diazenyl)-2-hydroxybenzaldehyde. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. 2012; 96: 493–500
Nazır H, Yıldız M, Yılmaz H, Tahir M.N, Ülkü D, Intramolecular hydrogen bonding and tautomerism in Schiff bases. Structure of N-(2-pyridil)-2-oxo-1-naphthlidenemethylamine. Journal of Molecular Structure. 2000; 524: 241-250
Pal M.K, Kushwah N, Wadawale AP, Manna D, Sudarsan V, Ghanty T.K, Jain V.K, Synthesis, characterization, photoluminescence and computational studies of mono- and diorgano-gallium complexes containing azo linked salicylaldimine Schiff bases. Journal of Organometallic Chemistry. 2015; 776: 98-106
Nagy P.I, Fabian W.M.F, Theoretical Study of the Enol Imine-Enaminone Tautomeric Equilibrium in Organic Solvents. J. Phys. Chem. B. 2006; 110: 25026-25032
Alaghaz A.M.A, Zayed M. E, Alharbi S. A, Synthesis, spectral characterization, molecular modeling and antimicrobial studies of tridentate azo-dye Schiff base metal complexes. Journal of Molecular Structure. 2015; 1084: 36–45
Qian H.F, Tao T, Feng Y.N, Wang Y.G, Huang W, Crystal structures, solvatochromisms and DFT computations of three disperse azo dyes having the same azobenzene skeleton. Journal of Molecular Structure. 2016; 1123: 305-310
Atay Ç.K, Gökalp M, Kart S.Ö, Tilki T, Mono azo dyes derived from 5-nitroanthranilic acid: Synthesis, absorption properties and DFT calculations. Journal of Molecular Structure. 2017; 1141: 237-244.
Sreenath M.C, Mathew S, Joe H.I, Rastogi V.K, Z-scan measurements of the third-order optical nonlinearities and vibrational spectral studies by DFT computations on azo dye 1-(2-Methylphenylazo)-2-napthol. Optics and Laser Technology. 2017; 97: 390–399.
Deshmukh M.S, Sekar N, A combined experimental and TD-DFT investigation of three disperse azo dyes having the nitroterephthalate skeleton. Dyes and Pigments. 2014; 103: 25-33
Turkten N, Cinar Z, Photocatalytic decolorization of azo dyes on TiO2: Prediction ofmechanism via conceptual DFT. Catalysis Today. 2017; 287: 169–175
Miraftab R, Ramezanzadeh B, Bahlakeh G, Mahdavian M, An advanced approach for fabricating a reduced graphene oxide-AZO dye/polyurethane composite with enhanced ultraviolet (UV) shielding. Chemical Engineering Journal. 2017; 321: 159–174
Erfantalab M, Khanmohammadi H, New 1,2,4-triazole-based azo–azomethine dye. Part III: Synthesis, characterization, thermal property, spectrophotometric and computational studies properties: Experimental and first-principles QM modeling. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. 2014; 125: 345–352
Gür M, Muğlu H, Çavus M.S, Güder A, Sayıner H.S, Kandemirli F, Synthesis, characterization, quantum chemical calculations and evaluation of antioxidant properties of 1,3,4-thiadiazole derivatives including 2- and 3-methoxy cinnamic acids. Journal of Molecular Structure. 2017; 1134: 40-50
Kohn W, Sham L.J, Self-consistent equations including exchange and correlation effects. Phys. Rev. 1965; 140: A1133.
Gaussian 09, Revision B.01, Frisch M. J, Trucks G. W, Schlegel H. B, Scuseria G. E, Robb M. A, Cheeseman J. R, Scalmani G., Barone V, Mennucci B, Petersson G. A, Nakatsuji H, Caricato M, Li X, Hratchian H. P, Izmaylov A. F, Bloino J, Zheng G, Sonnenberg J. L, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery J. A, Peralta J. E, Ogliaro F, Bearpark M, Heyd J. J, Brothers E, Kudin K. N, Staroverov V. N, Keith T, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant J. C, Iyengar S. S, Tomasi J, Cossi M, Rega N, Millam J. M, Klene M, Knox J. E, Cross J. B, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann R. E, Yazyev O, Austin A. J, Cammi R, Pomelli C, Ochterski J. W, Martin R. L, Morokuma K, Zakrzewski V. G, Voth G. A, Salvador P, Dannenberg J. J, Dapprich S, Daniels A. D, Farkas O, Foresman J. B, Ortiz J. V, Cioslowski J, Fox D. J, Gaussian, Inc., Wallingford CT, 2010.
Becke AD, A new mixing of HartreeeFock and local density-functional theories. J Chem Phys. 1993; 98:1372-7.
Lee C, Yang W, Parr RG. Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys Rev B 1988; 37: 785-9.
Cossi M, Barone V, Cammi R, Tomasi J., Ab initio study of solvated molecules: a new implementation of the polarizable continuum model, Chem. Phys. Lett. 1996;255: 327-335.

Toplam 27 adet kaynakça vardır.

Ayrıntılar

Konular	Mühendislik, Kimya Mühendisliği
Bölüm	Makaleler
Yazarlar	Sevil Özkınalı Muhammet Serdar Çavuş Büşra Umur Sakin Bu kişi benim
Yayımlanma Tarihi	1 Eylül 2017
Gönderilme Tarihi	24 Ekim 2017
Kabul Tarihi	24 Kasım 2017
Yayımlandığı Sayı	Yıl 2018 Cilt: 5 Sayı: 1