BibTex RIS Kaynak Göster

Synthesis and Characterization of Schiff Base Polymer Dyes Containing Electron-Withdrawing and Electron Releasing Groups

Yıl 2017, Cilt: 45 Sayı: 1, 67 - 80, 01.03.2017

Öz

New thermally stable water soluble azo dye and azo-Schiff base polymer dyes were synthesized via conden- sation reaction of 4-methyl pyridine and poly- 4,4’-diamino biphenyl-2,2’-disulfonic acid with substituted azo-coupled 2-hydroxy-5- 4-nitrophenyl diazenyl benzaldehyde. For the structural analyses of synthesized substances FT-IR and NMR analysis, florescence and UV-Vis measurements for optical properties and the thermal behavior TG-DTA of the prepared dyes have been determined using thermogravimetric technique. Azomethine dyes AZOBMS and AZOBMSP have relatively higher thermal durability in comparison to azo dye AZOBM . The solvatochromic studies of the prepared dyes in DMSO, DMF, CH3CN and THF. In addition, spect- rophotometric and spectrofluorometric studies showed that these dyes were good absorbent and fluorescent. The effect of various organic solvents with different polarities on the UV-Vis spectra and fluorescence analyses of the dyes has been also studied.

Kaynakça

  • H.M. Marwani, M. Abdullah, M.A. Asiri, A.S. Khan, Spectrophotometric and spectrofluorimetric studies of novel heterocyclic Schiff base dyes, Arabian J of Chem.,7 (2014) 609-614.
  • S. Menati, A. Azadbakht, R. Azadbakht, A. Taeb, A. Kakanejadifard, Synthesis, characterization, and electrochemical study of some novel, azo-containing Schiff bases and their Ni(II) complexes, Dyes and Pigments, 98 (2013) 499-506.
  • Y.X. Li, Q.Y. Wu, D.D. Gua, X.F. Gan, Optical characterization and blu-ray recording properties of metal(II) azo barbituric acid complex films, Mater. Sci. Eng. B, 158 (2009) 53–57.
  • W. Chen, Q.Y Wu, H.D. Gu, X.F. Gan, Synthesis, optical and thermal characterization of novel thiazolyl heterocyclic azo dye, Mater. Lett., 61 (2007) 4181– 4184.
  • S. Alghool, A.H. El-Halim, A. Dahshan, Synthesis, spectroscopic thermal and biological activity studies on azo-containing Schiff base dye and its Cobalt(II), Chromium(III) and Strontium(II) complexes, Journal of Molecular Structure, 938 (2010) 32-38.
  • H. Khanmohammadi, K. Rezaeian, M.M. Amini, W.S. Ng, Azo-azomethine dyes with N, O, S donor set of atoms and their Ni(II) complexes: Synthesis, characterization and spectral properties, Dyes and Pigments, 98 (2013) 557-564.
  • G. Kurtoğlu, B. Avar, H. Zengin, M. Kose, K. Sayin, M. Kurtoğlu, A novel azo-azomethine based fluorescent dye and its Co(II) and Cu(II) metal chelates, Journal of Molecular Liquids, 200 (2014) 105-114.
  • H. Khanmohammadi, K. Rezaeian, Thermally stable water insoluble azo-azomethine dyes: Synthesis, characterization and solvatochromic properties, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 97 (2012) 652-658.
  • T. Oktem, H. Ayhan, N. Seventekin, E. Pişkin, Modification of polyester fabrics by in situ plasma or post-plasma polymerisation of acrylic acid, Journal of the Society of Dyers and Colorists, 115 (1999) 274- 279.
  • F.M.W. Fabian, L. Antonov, D. Nedeltcheva, S.F. Kamounah, J.P. Taylor, Tautomerism in Hydroxynaphthaldehyde Anils and Azo Analogues:? a Combined Experimental and Computational Study, J. Phys. Chem. A, 108 (2004), 7603–7612.
  • H. Khanmohammadi, M. Darvishpour, New azo ligands containing azomethine groups in the pyridazine- based chain: Synthesis and characterization, Dyes Pigments, 81 (2009) 167–173.
  • S.M. Ho, A. Natansohn, P. Rochon, Azo Polymers for Reversible Optical Storage. 7. The Effect of the Size of the Photochromic Groups, Macromolecules, 28 (1995), 6124-6127.
  • J.C. Chang, T.W. Whang, C.C. Hsu, Y. Z. Ding, Y. K. Hsu, H.S. Lin, Synthesis and Relationships between the Nonlinear Optical and Holographic Properties of Dual Functional Azocarbazole Chromophores Based on Photorefractive Polymers, Macromolecules, 32 (1999) 5637-5646.
  • S. Uruş, S. Purtaş, G. Ceyhan, F. Tümer, Solid phase extraction of Pb(II), Cu(II), Cd(II) and Cr(III) with syringe technique using novel silica-supported bis(diazoimine) ligands, Chemical Engineering J., 220 (2013) 420-430.
  • I. Kaya, M. Yıldırım, M. Kamacı, Synthesis and characterization of new polyphenols derived from o-dianisidine: The effect of substituent on solubility, thermal stability, and electrical conductivity, optical and electrochemical properties, Eur Polym J., 45 (2009) 1586-1598.
  • D. Senol, I. Kaya, Synthesis and Characterization of Novel Polyamines Containing Different Substitute Groups Via Chemical Oxidative Polymerization, Journal of the Chinese Chemical Society, 62 (2015) 429-438.
  • D. Canakcı, M. Tuncel, H. Mart, S. Serin, New soluble azophenol polymers prepared by oxidative polycondensation, Polymer International, 56 (2007) 1537-1543.
  • B. Babür, N. Ertan, Part 1: Synthesis and visible absorption spectra of some new monoazo dyes derived from ethyl 2-amino-4-(4’-substitutedphenyl) thiophenes, Spectrochimica Acta Part A-molecular and Biomolecular Spectroscopy, 131 (2014) 319-328.
  • M. Kojima, S. Nebashi, K. Ogawa, N. Kurita, Effect of solvent on cis-to-trans isomerization of 4-hydroxyazobenzene aggregated through intermolecular hydrogen bonds, J. Phys. Org. Chem., 18 (2005) 994-1000.
  • I. Kaya, M. Yıldırım, A. Aydın, D. Senol, Synthesis and characterization of fluorescent graft fluorene-co- polyphenol derivatives: The effect of substituent on solubility, thermal stability, conductivity, optical and electrochemical properties, Reactive and Functional Polymers, 70 (2010) 815-826.
  • F. Nuralin, Bazı dispers azo boyar maddelerinin sentezi, absorbsiyon spektrumlarının ve boyama özelliklerinin incelenmesi (2006), Thesis, Gazi University, Turkey.

Elektron Salıcı ve Electron Çekici Grup İçeren Schiff Bazı Polimer Boyaların Sentez ve Karakterizasyonu

Yıl 2017, Cilt: 45 Sayı: 1, 67 - 80, 01.03.2017

Öz

Metil piridin ve poli 4,4’-diamino bifenil-2,2’-disülfonik asit ile 2-hidroksi-5- 4-nitrofenil4 diazenil benzaldehit bileşiği ile yeni ısıl kararlı suda çözünebilen azo boyaları ve azo-Schiff baz polimeri boyaları sentezlendi. Sentezlenen maddelerin yapısal analizleri FT-IR ve NMR, optik özellikleri için floresans ve UVVis ölçümleri, termogravimetri tekniği kullanılarak ısıl davranışları TG-DTA ölçüldü. Azometin boyaların AZOBMS ve AZOBMSP solvatokromik çalışmaları DMSO, DMF, CH3CN ve THF de yapıldı. Ayrıca farklı organik çözücülerde spektrofotometrik ve spektrofloremetrik çalışmaları sonucunda iyi absorban ve floresan özellik gösterdiği gözlendi

Kaynakça

  • H.M. Marwani, M. Abdullah, M.A. Asiri, A.S. Khan, Spectrophotometric and spectrofluorimetric studies of novel heterocyclic Schiff base dyes, Arabian J of Chem.,7 (2014) 609-614.
  • S. Menati, A. Azadbakht, R. Azadbakht, A. Taeb, A. Kakanejadifard, Synthesis, characterization, and electrochemical study of some novel, azo-containing Schiff bases and their Ni(II) complexes, Dyes and Pigments, 98 (2013) 499-506.
  • Y.X. Li, Q.Y. Wu, D.D. Gua, X.F. Gan, Optical characterization and blu-ray recording properties of metal(II) azo barbituric acid complex films, Mater. Sci. Eng. B, 158 (2009) 53–57.
  • W. Chen, Q.Y Wu, H.D. Gu, X.F. Gan, Synthesis, optical and thermal characterization of novel thiazolyl heterocyclic azo dye, Mater. Lett., 61 (2007) 4181– 4184.
  • S. Alghool, A.H. El-Halim, A. Dahshan, Synthesis, spectroscopic thermal and biological activity studies on azo-containing Schiff base dye and its Cobalt(II), Chromium(III) and Strontium(II) complexes, Journal of Molecular Structure, 938 (2010) 32-38.
  • H. Khanmohammadi, K. Rezaeian, M.M. Amini, W.S. Ng, Azo-azomethine dyes with N, O, S donor set of atoms and their Ni(II) complexes: Synthesis, characterization and spectral properties, Dyes and Pigments, 98 (2013) 557-564.
  • G. Kurtoğlu, B. Avar, H. Zengin, M. Kose, K. Sayin, M. Kurtoğlu, A novel azo-azomethine based fluorescent dye and its Co(II) and Cu(II) metal chelates, Journal of Molecular Liquids, 200 (2014) 105-114.
  • H. Khanmohammadi, K. Rezaeian, Thermally stable water insoluble azo-azomethine dyes: Synthesis, characterization and solvatochromic properties, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 97 (2012) 652-658.
  • T. Oktem, H. Ayhan, N. Seventekin, E. Pişkin, Modification of polyester fabrics by in situ plasma or post-plasma polymerisation of acrylic acid, Journal of the Society of Dyers and Colorists, 115 (1999) 274- 279.
  • F.M.W. Fabian, L. Antonov, D. Nedeltcheva, S.F. Kamounah, J.P. Taylor, Tautomerism in Hydroxynaphthaldehyde Anils and Azo Analogues:? a Combined Experimental and Computational Study, J. Phys. Chem. A, 108 (2004), 7603–7612.
  • H. Khanmohammadi, M. Darvishpour, New azo ligands containing azomethine groups in the pyridazine- based chain: Synthesis and characterization, Dyes Pigments, 81 (2009) 167–173.
  • S.M. Ho, A. Natansohn, P. Rochon, Azo Polymers for Reversible Optical Storage. 7. The Effect of the Size of the Photochromic Groups, Macromolecules, 28 (1995), 6124-6127.
  • J.C. Chang, T.W. Whang, C.C. Hsu, Y. Z. Ding, Y. K. Hsu, H.S. Lin, Synthesis and Relationships between the Nonlinear Optical and Holographic Properties of Dual Functional Azocarbazole Chromophores Based on Photorefractive Polymers, Macromolecules, 32 (1999) 5637-5646.
  • S. Uruş, S. Purtaş, G. Ceyhan, F. Tümer, Solid phase extraction of Pb(II), Cu(II), Cd(II) and Cr(III) with syringe technique using novel silica-supported bis(diazoimine) ligands, Chemical Engineering J., 220 (2013) 420-430.
  • I. Kaya, M. Yıldırım, M. Kamacı, Synthesis and characterization of new polyphenols derived from o-dianisidine: The effect of substituent on solubility, thermal stability, and electrical conductivity, optical and electrochemical properties, Eur Polym J., 45 (2009) 1586-1598.
  • D. Senol, I. Kaya, Synthesis and Characterization of Novel Polyamines Containing Different Substitute Groups Via Chemical Oxidative Polymerization, Journal of the Chinese Chemical Society, 62 (2015) 429-438.
  • D. Canakcı, M. Tuncel, H. Mart, S. Serin, New soluble azophenol polymers prepared by oxidative polycondensation, Polymer International, 56 (2007) 1537-1543.
  • B. Babür, N. Ertan, Part 1: Synthesis and visible absorption spectra of some new monoazo dyes derived from ethyl 2-amino-4-(4’-substitutedphenyl) thiophenes, Spectrochimica Acta Part A-molecular and Biomolecular Spectroscopy, 131 (2014) 319-328.
  • M. Kojima, S. Nebashi, K. Ogawa, N. Kurita, Effect of solvent on cis-to-trans isomerization of 4-hydroxyazobenzene aggregated through intermolecular hydrogen bonds, J. Phys. Org. Chem., 18 (2005) 994-1000.
  • I. Kaya, M. Yıldırım, A. Aydın, D. Senol, Synthesis and characterization of fluorescent graft fluorene-co- polyphenol derivatives: The effect of substituent on solubility, thermal stability, conductivity, optical and electrochemical properties, Reactive and Functional Polymers, 70 (2010) 815-826.
  • F. Nuralin, Bazı dispers azo boyar maddelerinin sentezi, absorbsiyon spektrumlarının ve boyama özelliklerinin incelenmesi (2006), Thesis, Gazi University, Turkey.
Toplam 21 adet kaynakça vardır.

Ayrıntılar

Birincil Dil Türkçe
Bölüm Research Article
Yazarlar

Dilek Şenol Bu kişi benim

Yayımlanma Tarihi 1 Mart 2017
Yayımlandığı Sayı Yıl 2017 Cilt: 45 Sayı: 1

Kaynak Göster

APA Şenol, D. (2017). Elektron Salıcı ve Electron Çekici Grup İçeren Schiff Bazı Polimer Boyaların Sentez ve Karakterizasyonu. Hacettepe Journal of Biology and Chemistry, 45(1), 67-80.
AMA Şenol D. Elektron Salıcı ve Electron Çekici Grup İçeren Schiff Bazı Polimer Boyaların Sentez ve Karakterizasyonu. HJBC. Mart 2017;45(1):67-80.
Chicago Şenol, Dilek. “Elektron Salıcı Ve Electron Çekici Grup İçeren Schiff Bazı Polimer Boyaların Sentez Ve Karakterizasyonu”. Hacettepe Journal of Biology and Chemistry 45, sy. 1 (Mart 2017): 67-80.
EndNote Şenol D (01 Mart 2017) Elektron Salıcı ve Electron Çekici Grup İçeren Schiff Bazı Polimer Boyaların Sentez ve Karakterizasyonu. Hacettepe Journal of Biology and Chemistry 45 1 67–80.
IEEE D. Şenol, “Elektron Salıcı ve Electron Çekici Grup İçeren Schiff Bazı Polimer Boyaların Sentez ve Karakterizasyonu”, HJBC, c. 45, sy. 1, ss. 67–80, 2017.
ISNAD Şenol, Dilek. “Elektron Salıcı Ve Electron Çekici Grup İçeren Schiff Bazı Polimer Boyaların Sentez Ve Karakterizasyonu”. Hacettepe Journal of Biology and Chemistry 45/1 (Mart 2017), 67-80.
JAMA Şenol D. Elektron Salıcı ve Electron Çekici Grup İçeren Schiff Bazı Polimer Boyaların Sentez ve Karakterizasyonu. HJBC. 2017;45:67–80.
MLA Şenol, Dilek. “Elektron Salıcı Ve Electron Çekici Grup İçeren Schiff Bazı Polimer Boyaların Sentez Ve Karakterizasyonu”. Hacettepe Journal of Biology and Chemistry, c. 45, sy. 1, 2017, ss. 67-80.
Vancouver Şenol D. Elektron Salıcı ve Electron Çekici Grup İçeren Schiff Bazı Polimer Boyaların Sentez ve Karakterizasyonu. HJBC. 2017;45(1):67-80.

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