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MOLECULAR STRUCTURE ANALYSIS AND SPECTROSCOPIC PROPERTIES OF MONOAZO DISPERSE DYE FROM N,N-DIMETHYLANILINE

Year 2017, Volume: 30 Issue: 1, 175 - 189, 14.03.2017

Abstract

A monoazo disperse dye (DMA) has been prepared by diazotizing 4-aminoacetophenone and coupling with N,N-dimetylaniline. It was fully characterized using IR, 1H-NMR, 13C-NMR and mass spectral techniques. Structural assignments of the dye were made using X-ray crystallographic methods. The electronic absorption spectra of the dye in solvents of different polarities covers a λmax range of 437-460 nm. It is showed that the compound exhibits positive solvatochromism in solution, namely the absorption band is red shifted with increasing solvent polarity. In addition, the absorption properties of the dye change drastically upon acidification, as the protonation of β-nitrogen atom of the azo group increases the donor-acceptor interplay of the π system. The molecular structure, spectroscopic and nonlinear optical (NLO) properties of azo dye have been also investigated theoretically by performing Density Functional Theory (DFT) and Hartree–Fock (HF) levels of theory using the 6-31+G(d,p) basis set. The optimized geometries, electronic absorption spectra calculated using time-dependent DFT (TD-DFT) method and NMR spectra are evaluated via comparison with experimental values. In addition, thermal analysis shows that this dye is thermally stable up to 258 oC.

References

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  • Hunger, K., Industrial Dyes, Chemistry, Properties, Applications 2nd ed., WILEY-VCH Verlag GmbH & Co. KgaA, Weinheim, (2003).
  • Berber, H., Ogretir, C., Lekesiz E.C.S., Ermis, E., “Spectroscopic Determination of Acidity Constants of Some Monoazo Resorcinol Derivatives”, J. Chem. Eng. Data, 53: 1049–1055, (2008).
  • Koh, J., Kim, S., Kim, J.P., “Synthesis and spectral properties of azohydroxypyridone disperse dyes containing a fluorosulphonyl group”, Color. Technol., 120: 241–246, (2004).
  • 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-4(5H)-one and study of their azo-hydrazone tautomerism”, Dyes Pigments, 99: 291–298, (2013).
  • Ferraz, E.R.A., Oliveira, G.A.R., Grando, M.D., Lizier, T.M., Zanoni, M.V.B., Oliveira, D., “Photoelectrocatalysis based on Ti/TiO2 nanotubes removes toxic properties of the azo dyes Disperse Red 1, Disperse Red 13 and Disperse Orange 1 from aqueous chloride samples”, J. Environ. Manage., 124: 108–114, (2013).
  • Bushuyev, O.S., Singleton, T.A., Barrett C.J., “Fast, Reversible, and General Photomechanical Motion in Single Crystals of Various Azo Compounds Using Visible Light”, Adv. Mater., 25: 1796–1800, (2013).
  • Henzl, J., Boom, K., Morgenstern, K., “Using the First Steps of Hydration for the Determination of Molecular Conformation of a Single Molecule”, J. Am. Chem. Soc.,136: 13341−13347, (2014).
  • Uliana, C.V., Garbellini, G.S., Yamanaka, H., “Electrochemical investigations on the capacity of flavonoids to protect DNA against damage caused by textile disperse dyes”, Sens. Actuators B: Chem., 192: 188–195, (2014).
  • Blumberg, S., Martin, S.F., “4-(Phenylazo)diphenylamine (PDA): a universal indicator for the colorimetric titration of strong bases, Lewis acids, and hydride reducing agents.”, Tetrahedron Lett., 56: 3674–3678, (2015).
  • Seclaman, E., Sallo, A., Elenes, F., Crasmareanu, C., Wikete, C., Timofei, S., Simon, Z., “Hydrophobicity, protolytic equilibrium and chromatographic behaviour of some monoazoic dyes”, Dyes Pigments, 55: 69–77(2002).
  • Towns A.D., “Developments in azo disperse dyes derived from heterocyclic diazo components”, Dyes Pigments, 42: 3–28, (1999).
  • Chao, Y.C., Lin, S.M., “Carboxy-substituted monoazo dyes for wool-polyester blends”, Dyes Pigments, 44: 209–218, (2000).
  • Ferraz, E.R.A, Oliveira, G.A.R., Grando, M.D., Lizier, T.M., Zanoni, M.V.B., Oliveira D.P., “Photoelectrocatalysis based on Ti/TiO2 nanotubes removes toxic properties of the azo dyes Disperse Red 1, Disperse Red 13 and Disperse Orange 1 from aqueous chloride samples”, J. Environ. Manage., 124: 108–114, (2013).
  • Uliana, C.V., Garbellini, G.S., Yamanaka, H., “Evaluation of the interactions of DNA with the textile dyes Disperse Orange 1 and Disperse Red 1 and their electrolysis products using an electrochemical biosensor”, Sens. Actuators B: Chem., 178: 627–635, (2013).
  • Miao S., Zhu Y., Zhuang, H., Xu, X., Li, H., Sun, R., Li, N., Ji, S., Lu, J., “Adjustment of charge trap number and depth in molecular backbone to achieve tunable multilevel data storage performance”, J. Mater. Chem. C, 1: 2320–2327 (2013).
  • Zhuang H., Zhang, Q., Zhu, Y., Xu, X., Liu, H., Najun, L., Xu, Q., Li, H., Lu, J., Wang, L., “Effects of terminal electron acceptor strength on film morphology and ternary memory performance of triphenylamine donor based devices”, J. Mater. Chem. C: 1 3816–3824, (2013).
  • Mourot, A., Kienzler, M.A., Banghart, M.R., Fehrentz, T., Huber, F.M.E., Stein, M., Kramer, R.H., Trauner, D., “Tuning Photochromic Ion Channel Blockers”, ACS Chem. Neurosci., 2: 536–543 (2011).
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  • Shin, D.M., Shanzea, K.Z., Whitten, D.G., “Solubilization Sites and Orientations in Microheterogeneous Media. Studies Using Donor-Acceptor-Substituted Azobenzenes and Bichromophoric Solvatochromic Molecules”, J. Am. Chem. Soc., 111: 8494–8501, (1989).
  • Ishow, E., Bellaiche, C., Bouteiller, L., Nakatani, K., Delaire, J.A., “Versatile Synthesis of Small NLO-Active Molecules Forming Amorphous Materials with Spontaneous Second-Order NLO Response”, J. Am. Chem. Soc., 125: 15744–15745, (2003).
  • Babür, B., Seferoglu, N., Aktan, E., Hökelek, T., Sahin, E., Seferoglu, Z., “Phenylazoindole dyes 3: Determination of azo-hydrazone tautomers of new phenylazoindole dyes in solution and solid state”, J. Mol. Struct.,1081: 175–181, (2015).
  • Aktan, E., Babür, B., Seferoğlu, Z., Hökelek, T., Şahin, E., “Synthesis and structure of a novel hetarylazoindole dye studied by X-ray diffraction, FT-IR, FT-Raman, UV–vis, NMR spectra and DFT calculations”, J. Mol. Struct., 1002: 113–120, (2011).
  • Babür, B., Seferoglu, N., Aktan, E., Hökelek, T., Sahin, E., Seferoglu, Z., “Phenylazoindole dyes 2: The molecular structure characterizations of new phenylazo indoles derived from 1,2-dimethylindole”, Dyes Pigments, 103: 62–70, (2014).
  • Aksungur, T., Arslan, Ö., Seferoglu, N., Seferoglu, Z., “Photophysical and theoretical studies on newly synthesized N,N-diphenylamine based azo dye”, J. Mol. Struct., 1099: 543–550, (2015).
  • Bruker, 'Bruker SAINT' and 'Bruker APEX2' software programs. Bruker AXS Inc., Madison, Wisconsin, USA(2007).
  • Sheldrick, G.M., SHELXS97 and SHELXL97, University of Göttingen, Germany, (1997).
  • Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., et al. Gaussian 09, revision A.2. Wallingford CT: Gaussian, Inc. (2009).
  • Becke, A.D., “A new mixing of HartreeeFock and local density-functional theories”, J. Chem. Phys., 98: 1372–1377, (1993).
  • Lee, C., Yang, W., Parr, R.G., “Development of the Colle-Salvetti correlation-energyformula into a functional of the electron density”, Phys. Rev. B, 37: 785–789, (1988).
  • Tomasi, J., Mennucci, B., Cammi, R., “Quantum mechanical continuum solvation models”, Chem. Rev.105: 2999–3094, (2005).
  • Wolinski, K., Hilton, J.F., Pulay, P., “Efficient Implementation of the Gauge-Independent Atomic Orbital Method for NMR Chemical Shift Calculations”, J. Am. Chem. Soc. 112: 8251-8260, (1990).
  • Hohenberg, P., Kohn, W., “Inhomogeneous Electron Gas”, Phys. Rev., 136: B864, (1964).
  • Kohn, W. and Sham, L. J., “Self-Consistent Equations Including Exchange andCorrelation Effects”, Phys. Rev. 140: A1133, (1965).
Year 2017, Volume: 30 Issue: 1, 175 - 189, 14.03.2017

Abstract

References

  • Zollinger, H., Color Chemistry, Synthesis, Properties and Applications of Organic Dyes and Pigments 3th ed., Wiley-VCH, (2003).
  • Hunger, K., Industrial Dyes, Chemistry, Properties, Applications 2nd ed., WILEY-VCH Verlag GmbH & Co. KgaA, Weinheim, (2003).
  • Berber, H., Ogretir, C., Lekesiz E.C.S., Ermis, E., “Spectroscopic Determination of Acidity Constants of Some Monoazo Resorcinol Derivatives”, J. Chem. Eng. Data, 53: 1049–1055, (2008).
  • Koh, J., Kim, S., Kim, J.P., “Synthesis and spectral properties of azohydroxypyridone disperse dyes containing a fluorosulphonyl group”, Color. Technol., 120: 241–246, (2004).
  • 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-4(5H)-one and study of their azo-hydrazone tautomerism”, Dyes Pigments, 99: 291–298, (2013).
  • Ferraz, E.R.A., Oliveira, G.A.R., Grando, M.D., Lizier, T.M., Zanoni, M.V.B., Oliveira, D., “Photoelectrocatalysis based on Ti/TiO2 nanotubes removes toxic properties of the azo dyes Disperse Red 1, Disperse Red 13 and Disperse Orange 1 from aqueous chloride samples”, J. Environ. Manage., 124: 108–114, (2013).
  • Bushuyev, O.S., Singleton, T.A., Barrett C.J., “Fast, Reversible, and General Photomechanical Motion in Single Crystals of Various Azo Compounds Using Visible Light”, Adv. Mater., 25: 1796–1800, (2013).
  • Henzl, J., Boom, K., Morgenstern, K., “Using the First Steps of Hydration for the Determination of Molecular Conformation of a Single Molecule”, J. Am. Chem. Soc.,136: 13341−13347, (2014).
  • Uliana, C.V., Garbellini, G.S., Yamanaka, H., “Electrochemical investigations on the capacity of flavonoids to protect DNA against damage caused by textile disperse dyes”, Sens. Actuators B: Chem., 192: 188–195, (2014).
  • Blumberg, S., Martin, S.F., “4-(Phenylazo)diphenylamine (PDA): a universal indicator for the colorimetric titration of strong bases, Lewis acids, and hydride reducing agents.”, Tetrahedron Lett., 56: 3674–3678, (2015).
  • Seclaman, E., Sallo, A., Elenes, F., Crasmareanu, C., Wikete, C., Timofei, S., Simon, Z., “Hydrophobicity, protolytic equilibrium and chromatographic behaviour of some monoazoic dyes”, Dyes Pigments, 55: 69–77(2002).
  • Towns A.D., “Developments in azo disperse dyes derived from heterocyclic diazo components”, Dyes Pigments, 42: 3–28, (1999).
  • Chao, Y.C., Lin, S.M., “Carboxy-substituted monoazo dyes for wool-polyester blends”, Dyes Pigments, 44: 209–218, (2000).
  • Ferraz, E.R.A, Oliveira, G.A.R., Grando, M.D., Lizier, T.M., Zanoni, M.V.B., Oliveira D.P., “Photoelectrocatalysis based on Ti/TiO2 nanotubes removes toxic properties of the azo dyes Disperse Red 1, Disperse Red 13 and Disperse Orange 1 from aqueous chloride samples”, J. Environ. Manage., 124: 108–114, (2013).
  • Uliana, C.V., Garbellini, G.S., Yamanaka, H., “Evaluation of the interactions of DNA with the textile dyes Disperse Orange 1 and Disperse Red 1 and their electrolysis products using an electrochemical biosensor”, Sens. Actuators B: Chem., 178: 627–635, (2013).
  • Miao S., Zhu Y., Zhuang, H., Xu, X., Li, H., Sun, R., Li, N., Ji, S., Lu, J., “Adjustment of charge trap number and depth in molecular backbone to achieve tunable multilevel data storage performance”, J. Mater. Chem. C, 1: 2320–2327 (2013).
  • Zhuang H., Zhang, Q., Zhu, Y., Xu, X., Liu, H., Najun, L., Xu, Q., Li, H., Lu, J., Wang, L., “Effects of terminal electron acceptor strength on film morphology and ternary memory performance of triphenylamine donor based devices”, J. Mater. Chem. C: 1 3816–3824, (2013).
  • Mourot, A., Kienzler, M.A., Banghart, M.R., Fehrentz, T., Huber, F.M.E., Stein, M., Kramer, R.H., Trauner, D., “Tuning Photochromic Ion Channel Blockers”, ACS Chem. Neurosci., 2: 536–543 (2011).
  • Carolina V., Uliana, G.S., Yamanaka, G.H., “Electrochemical reduction of Disperse Orange 1 textile dye at a boron-doped diamond electrode”, J. Appl. Electrochem., 42: 297–304, (2012).
  • Shin, D.M., Shanzea, K.Z., Whitten, D.G., “Solubilization Sites and Orientations in Microheterogeneous Media. Studies Using Donor-Acceptor-Substituted Azobenzenes and Bichromophoric Solvatochromic Molecules”, J. Am. Chem. Soc., 111: 8494–8501, (1989).
  • Ishow, E., Bellaiche, C., Bouteiller, L., Nakatani, K., Delaire, J.A., “Versatile Synthesis of Small NLO-Active Molecules Forming Amorphous Materials with Spontaneous Second-Order NLO Response”, J. Am. Chem. Soc., 125: 15744–15745, (2003).
  • Babür, B., Seferoglu, N., Aktan, E., Hökelek, T., Sahin, E., Seferoglu, Z., “Phenylazoindole dyes 3: Determination of azo-hydrazone tautomers of new phenylazoindole dyes in solution and solid state”, J. Mol. Struct.,1081: 175–181, (2015).
  • Aktan, E., Babür, B., Seferoğlu, Z., Hökelek, T., Şahin, E., “Synthesis and structure of a novel hetarylazoindole dye studied by X-ray diffraction, FT-IR, FT-Raman, UV–vis, NMR spectra and DFT calculations”, J. Mol. Struct., 1002: 113–120, (2011).
  • Babür, B., Seferoglu, N., Aktan, E., Hökelek, T., Sahin, E., Seferoglu, Z., “Phenylazoindole dyes 2: The molecular structure characterizations of new phenylazo indoles derived from 1,2-dimethylindole”, Dyes Pigments, 103: 62–70, (2014).
  • Aksungur, T., Arslan, Ö., Seferoglu, N., Seferoglu, Z., “Photophysical and theoretical studies on newly synthesized N,N-diphenylamine based azo dye”, J. Mol. Struct., 1099: 543–550, (2015).
  • Bruker, 'Bruker SAINT' and 'Bruker APEX2' software programs. Bruker AXS Inc., Madison, Wisconsin, USA(2007).
  • Sheldrick, G.M., SHELXS97 and SHELXL97, University of Göttingen, Germany, (1997).
  • Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., et al. Gaussian 09, revision A.2. Wallingford CT: Gaussian, Inc. (2009).
  • Becke, A.D., “A new mixing of HartreeeFock and local density-functional theories”, J. Chem. Phys., 98: 1372–1377, (1993).
  • Lee, C., Yang, W., Parr, R.G., “Development of the Colle-Salvetti correlation-energyformula into a functional of the electron density”, Phys. Rev. B, 37: 785–789, (1988).
  • Tomasi, J., Mennucci, B., Cammi, R., “Quantum mechanical continuum solvation models”, Chem. Rev.105: 2999–3094, (2005).
  • Wolinski, K., Hilton, J.F., Pulay, P., “Efficient Implementation of the Gauge-Independent Atomic Orbital Method for NMR Chemical Shift Calculations”, J. Am. Chem. Soc. 112: 8251-8260, (1990).
  • Hohenberg, P., Kohn, W., “Inhomogeneous Electron Gas”, Phys. Rev., 136: B864, (1964).
  • Kohn, W. and Sham, L. J., “Self-Consistent Equations Including Exchange andCorrelation Effects”, Phys. Rev. 140: A1133, (1965).
There are 34 citations in total.

Details

Journal Section Chemistry
Authors

Nurgul Seferoglu This is me

Ömer Arslan This is me

Ergin Yalçın This is me

Müjgan Yaman

Zeynel Seferoglu

Publication Date March 14, 2017
Published in Issue Year 2017 Volume: 30 Issue: 1

Cite

APA Seferoglu, N., Arslan, Ö., Yalçın, E., Yaman, M., et al. (2017). MOLECULAR STRUCTURE ANALYSIS AND SPECTROSCOPIC PROPERTIES OF MONOAZO DISPERSE DYE FROM N,N-DIMETHYLANILINE. Gazi University Journal of Science, 30(1), 175-189.
AMA Seferoglu N, Arslan Ö, Yalçın E, Yaman M, Seferoglu Z. MOLECULAR STRUCTURE ANALYSIS AND SPECTROSCOPIC PROPERTIES OF MONOAZO DISPERSE DYE FROM N,N-DIMETHYLANILINE. Gazi University Journal of Science. March 2017;30(1):175-189.
Chicago Seferoglu, Nurgul, Ömer Arslan, Ergin Yalçın, Müjgan Yaman, and Zeynel Seferoglu. “MOLECULAR STRUCTURE ANALYSIS AND SPECTROSCOPIC PROPERTIES OF MONOAZO DISPERSE DYE FROM N,N-DIMETHYLANILINE”. Gazi University Journal of Science 30, no. 1 (March 2017): 175-89.
EndNote Seferoglu N, Arslan Ö, Yalçın E, Yaman M, Seferoglu Z (March 1, 2017) MOLECULAR STRUCTURE ANALYSIS AND SPECTROSCOPIC PROPERTIES OF MONOAZO DISPERSE DYE FROM N,N-DIMETHYLANILINE. Gazi University Journal of Science 30 1 175–189.
IEEE N. Seferoglu, Ö. Arslan, E. Yalçın, M. Yaman, and Z. Seferoglu, “MOLECULAR STRUCTURE ANALYSIS AND SPECTROSCOPIC PROPERTIES OF MONOAZO DISPERSE DYE FROM N,N-DIMETHYLANILINE”, Gazi University Journal of Science, vol. 30, no. 1, pp. 175–189, 2017.
ISNAD Seferoglu, Nurgul et al. “MOLECULAR STRUCTURE ANALYSIS AND SPECTROSCOPIC PROPERTIES OF MONOAZO DISPERSE DYE FROM N,N-DIMETHYLANILINE”. Gazi University Journal of Science 30/1 (March 2017), 175-189.
JAMA Seferoglu N, Arslan Ö, Yalçın E, Yaman M, Seferoglu Z. MOLECULAR STRUCTURE ANALYSIS AND SPECTROSCOPIC PROPERTIES OF MONOAZO DISPERSE DYE FROM N,N-DIMETHYLANILINE. Gazi University Journal of Science. 2017;30:175–189.
MLA Seferoglu, Nurgul et al. “MOLECULAR STRUCTURE ANALYSIS AND SPECTROSCOPIC PROPERTIES OF MONOAZO DISPERSE DYE FROM N,N-DIMETHYLANILINE”. Gazi University Journal of Science, vol. 30, no. 1, 2017, pp. 175-89.
Vancouver Seferoglu N, Arslan Ö, Yalçın E, Yaman M, Seferoglu Z. MOLECULAR STRUCTURE ANALYSIS AND SPECTROSCOPIC PROPERTIES OF MONOAZO DISPERSE DYE FROM N,N-DIMETHYLANILINE. Gazi University Journal of Science. 2017;30(1):175-89.