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Yeni Heterosiklik Azo Bileşikler: Sentez, Karakterizasyon ve DFT Hesaplamaları

Year 2020, , 319 - 329, 29.11.2020
https://doi.org/10.29233/sdufeffd.820455

Abstract

Günümüzde yeni azo bileşikleri sentezlemek ile birlikte farklı kullanım alanlarında da araştırma yapmak büyük önem taşımaktadır. Kâğıt, gıda, kozmetik, tekstil ve deri gibi birçok sektörde kullanım alanları olduğu gibi yüksek teknoloji ürünlerinde de (lazer baskı materyelleri, yazıcı tonerleri, sıvı kristaller vb.) birden fazla kullanım alanı her geçen gün giderek artmaktadır. Bu çalışmada, bu avantajlar göz önünde bulundurarak, başlangıç maddeleri olarak 3-amino-1H-pirazol-5-ol, 1H-1,2,4-triazol-3-amin, 3-amino-1H-fenil-5-ol bileşiklerinin diazonyum tuzlarının resorsinol ve 3,5-dihidroksi benzoik asitle azo kenetlenmesi sonucu yeni azo bileşikleri sentezlenerek, yapıları FT-IR, 1H-NMR gibi spektroskopik yöntemlerle karakterize edilmiş ve görünür bölge absorpsiyon spektrumları üzerine farklı çözücü etkisi araştırılmıştır. Sentezlenen moleküllerin moleküler geometrisi hesaplamaları, 6-311G (d,p) temel seti ile B3LYP seviyesi kullanılarak Yoğunluk Fonksiyonel Teorisi (DFT) ile yapılmıştır. Ayrıca HOMO-LUMO orbital hesaplamaları zamana bağlı DFT (TD-DFT) yaklaşımı ile gerçekleştirilmiştir. Yapılmış olan bu çalışma sonucunda heterosiklik amin grubu içeren azo bileşiklerinin batokromik etkiye ve parlak renklere sahip olduğu gözlemlenmiştir. Bu çalışma, literatüre ve boyarmadde endüstrisine önemli katkılar sağlayacağı ve potansiyel uygulamalara temel oluşturacağı öngörülmektedir.

Supporting Institution

Süleyman Demirel Üniversitesi Bilimsel Araştırma Projeleri Koordinasyon Birimi

Project Number

FYL-2019-7399

Thanks

Bu çalışmanın gerçekleştirilmesi için gerekli finansal destekleri için SDÜ-BAP (FYL-2019-7399) birimine teşekkür ederiz.

References

  • [1] M.R. Maliyappa, J. Keshavayya, M. Mahanthappa, Y. Shivaraj, K.V. Basavarajappa, ''6-Substituted benzothiazole based dispersed azo dyes having pyrazole moiety: Synthesis, characterization, electrochemical and DFT studies,'' J. Mol. Struct, 1199, 126959, 2020.
  • [2] M.N. Matada, K. Jathi, P. Malingappa, I. Pushpavathi, ''Synthesis, spectroscopic, DFT and electrochemical studies of heterocyclic azo dyes derived from 1-{[(E)-benzylideneamino](phenyl) methyl} naphthalen-2-ol,'' Chem. Data Collect, 25, 100314, 2020.
  • [3] M.A. Arafath, F. Adam, F.S.R. Al-Suede, M.R. Razali, M.B.K. Ahamed, A.M.S. Abdul Majid, M.Z. Hassan, H. Osman, S. Abubakar, ''Synthesis, characterization, X-ray crystal structures of heterocyclic Schiff base compounds and in vitro cholinesterase inhibition and anticancer activity,'' J. Mol. Struct, 1149, 216–228, 2017.
  • [4] A.Z. El-Sonbati, M.A. Diab, A.A. El-Bindary, A.F. Shoair, M.A. Hussein, R.A. El-Boz, ''Spectroscopic, thermal, catalytic and biological studies of Cu(II) azo dye complexes,'' J. Mol. Struct, 1141, 186–203, 2017.
  • [5] F.L. Coelho, C. de Á. Braga, G.M. Zanotto, E.S. Gil, L.F. Campo, P.F.B. Gonçalves, F.S. Rodembusch, F. da S. Santos, ''Low pH optical sensor based on benzothiazole azo dyes,'' Sens. Actuators B Chem, 259, 514–525, 2018.
  • [6] F. Borbone, A. Carella, L. Ricciotti, A. Tuzi, A. Roviello, A. Barsella, ''High nonlinear optical response in 4-chlorothiazole-based azo dyes,'' Dyes Pigm, 88, 290–295, 2011.
  • [7] O. V. Kovalchukova, M.A. Ryabov, P. V. Dorovatovskii, Y. V. Zubavichus, A.N. Utenyshev, D.N. Kuznetsov, O. V. Volyansky, V.K. Voronkova, V.N. Khrustalev, ''Synthesis and characterization of a series of novel metal complexes of N-heterocyclic azo-colorants derived from 4-azo-pyrazol-5-one,'' Polyhedron, 121, 41–52, 2017.
  • [8] M.R. Yazdanbakhsh, A. Mohammadi, M. Abbasnia, ''Some heterocyclic azo dyes derived from thiazolyl derivatives; synthesis; substituent effects and solvatochromic studies,'' Spectrochim. Acta A Mol. Biomol. Spectrosc, 77, 1084–1087, 2010.
  • [9] Ç. Karabacak Atay, M. Gökalp, B.Ö. Tuncer, T. Tilki, ''Antimicrobial activities and absorption properties of disazo dyes containing imidazole and pyrazole moieties,'' J. Macromol. Sci. A, 54, 236–242, 2017.
  • [10] Ç. Karabacak, T. Tilki, B.Ö. Tuncer, M. Cengiz, ''Antimicrobial pyrazole dyes: synthesis, characterization, and absorption characteristics,'' Res. Chem. Intermed, 41, 1985–1999, 2015.
  • [11] S.M. Bachrach, Computational Organic Chemistry, John Wiley & Sons, Inc., Hoboken, NJ, USA, 2014.
  • [12] I.L. Shegal, K. V. Stanovkina, N.G. Kovalenko, L.M. Shegal, ''Synthesis of azo compounds containing triazole and tetrazole residues,'' Chem Heterocycl Compd, 10, 369–371, 1974.
  • [13] M. Gökalp, B. Dede, T. Tilki, Ç. Karabacak Atay, ''Triazole based azo molecules as potential antibacterial agents: Synthesis, characterization, DFT, ADME and molecular docking studies,'' J. Mol. Struct, 1212, 128140, 2020.
  • [14] M.J. Frisch, G.W. Trucks, H.B. Schlegel et al., Gaussian 09, Revision E.01, Gaussian, Inc., Wallingford CT, 2016.
  • [15] R. Dennington, T.A. Keith, J.M. Millam GaussView, Revision 5.0.9, Semichem. Inc. Shawnee Mission, KS, 2009.
  • [16] A.D. Becke, ''Density‐functional thermochemistry. III. The role of exact exchange,'' J. Chem. Phys, 98, 5648–5652, 1993.
  • [17] P.J. Stephens, F.J. Devlin, C.F. Chabalowski, M.J. Frisch, ''Ab Initio Calculation of Vibrational Absorption and Circular Dichroism Spectra Using Density Functional Force Fields,'' J. Chem. Phys, 98, 11623–11627, 1994.
  • [18] C. Lee, W. Yang, R.G. Parr, ''Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density,'' Phys. Rev. B, 37, 785–789, 1988.

Novel Heterocyclic Azo Compounds: Synthesis, Characterization and DFT Calculations

Year 2020, , 319 - 329, 29.11.2020
https://doi.org/10.29233/sdufeffd.820455

Abstract

Today, it is of great importance to synthesize new azo compounds as well as to conduct research in different areas of use. More than one usage area is increasing day by day in high-tech products (laser printing materials, printer toners, liquid crystals, etc.) as well as in many sectors such as paper, food, cosmetics, textile and leather. In this study, considering these advantages, the compounds of 3-amino-1H-pyrazol-5-ol, 1H-1,2,4-triazol-3-amine, 3-amino-1H-phenyl-5-ol were used as starting materials. As a result of azo coupling of diazonium salts with resorcinol and 3,5-dihydroxy benzoic acid, new azo compounds were synthesized, their structures were characterized by spectroscopic methods such as FT-IR and 1H-NMR, and different solvent effects on visible absorption spectra were investigated. Molecular geometry and vibration frequency calculations of synthesized compounds were made with Density Functional Theory (DFT) using 6-311G (d,p) basis set and B3LYP level. Additional, electronic properties and HOMO-LUMO orbital calculations were carried out with time dependent DFT (TD-DFT) approach. As a result of this study, it has been observed that azo compounds containing heterocyclic amine groups have batchromic effects and bright colors. It is anticipated that this study will make important contributions to the literature and the dyestuff industry and will form a basis for potential applications.

Project Number

FYL-2019-7399

References

  • [1] M.R. Maliyappa, J. Keshavayya, M. Mahanthappa, Y. Shivaraj, K.V. Basavarajappa, ''6-Substituted benzothiazole based dispersed azo dyes having pyrazole moiety: Synthesis, characterization, electrochemical and DFT studies,'' J. Mol. Struct, 1199, 126959, 2020.
  • [2] M.N. Matada, K. Jathi, P. Malingappa, I. Pushpavathi, ''Synthesis, spectroscopic, DFT and electrochemical studies of heterocyclic azo dyes derived from 1-{[(E)-benzylideneamino](phenyl) methyl} naphthalen-2-ol,'' Chem. Data Collect, 25, 100314, 2020.
  • [3] M.A. Arafath, F. Adam, F.S.R. Al-Suede, M.R. Razali, M.B.K. Ahamed, A.M.S. Abdul Majid, M.Z. Hassan, H. Osman, S. Abubakar, ''Synthesis, characterization, X-ray crystal structures of heterocyclic Schiff base compounds and in vitro cholinesterase inhibition and anticancer activity,'' J. Mol. Struct, 1149, 216–228, 2017.
  • [4] A.Z. El-Sonbati, M.A. Diab, A.A. El-Bindary, A.F. Shoair, M.A. Hussein, R.A. El-Boz, ''Spectroscopic, thermal, catalytic and biological studies of Cu(II) azo dye complexes,'' J. Mol. Struct, 1141, 186–203, 2017.
  • [5] F.L. Coelho, C. de Á. Braga, G.M. Zanotto, E.S. Gil, L.F. Campo, P.F.B. Gonçalves, F.S. Rodembusch, F. da S. Santos, ''Low pH optical sensor based on benzothiazole azo dyes,'' Sens. Actuators B Chem, 259, 514–525, 2018.
  • [6] F. Borbone, A. Carella, L. Ricciotti, A. Tuzi, A. Roviello, A. Barsella, ''High nonlinear optical response in 4-chlorothiazole-based azo dyes,'' Dyes Pigm, 88, 290–295, 2011.
  • [7] O. V. Kovalchukova, M.A. Ryabov, P. V. Dorovatovskii, Y. V. Zubavichus, A.N. Utenyshev, D.N. Kuznetsov, O. V. Volyansky, V.K. Voronkova, V.N. Khrustalev, ''Synthesis and characterization of a series of novel metal complexes of N-heterocyclic azo-colorants derived from 4-azo-pyrazol-5-one,'' Polyhedron, 121, 41–52, 2017.
  • [8] M.R. Yazdanbakhsh, A. Mohammadi, M. Abbasnia, ''Some heterocyclic azo dyes derived from thiazolyl derivatives; synthesis; substituent effects and solvatochromic studies,'' Spectrochim. Acta A Mol. Biomol. Spectrosc, 77, 1084–1087, 2010.
  • [9] Ç. Karabacak Atay, M. Gökalp, B.Ö. Tuncer, T. Tilki, ''Antimicrobial activities and absorption properties of disazo dyes containing imidazole and pyrazole moieties,'' J. Macromol. Sci. A, 54, 236–242, 2017.
  • [10] Ç. Karabacak, T. Tilki, B.Ö. Tuncer, M. Cengiz, ''Antimicrobial pyrazole dyes: synthesis, characterization, and absorption characteristics,'' Res. Chem. Intermed, 41, 1985–1999, 2015.
  • [11] S.M. Bachrach, Computational Organic Chemistry, John Wiley & Sons, Inc., Hoboken, NJ, USA, 2014.
  • [12] I.L. Shegal, K. V. Stanovkina, N.G. Kovalenko, L.M. Shegal, ''Synthesis of azo compounds containing triazole and tetrazole residues,'' Chem Heterocycl Compd, 10, 369–371, 1974.
  • [13] M. Gökalp, B. Dede, T. Tilki, Ç. Karabacak Atay, ''Triazole based azo molecules as potential antibacterial agents: Synthesis, characterization, DFT, ADME and molecular docking studies,'' J. Mol. Struct, 1212, 128140, 2020.
  • [14] M.J. Frisch, G.W. Trucks, H.B. Schlegel et al., Gaussian 09, Revision E.01, Gaussian, Inc., Wallingford CT, 2016.
  • [15] R. Dennington, T.A. Keith, J.M. Millam GaussView, Revision 5.0.9, Semichem. Inc. Shawnee Mission, KS, 2009.
  • [16] A.D. Becke, ''Density‐functional thermochemistry. III. The role of exact exchange,'' J. Chem. Phys, 98, 5648–5652, 1993.
  • [17] P.J. Stephens, F.J. Devlin, C.F. Chabalowski, M.J. Frisch, ''Ab Initio Calculation of Vibrational Absorption and Circular Dichroism Spectra Using Density Functional Force Fields,'' J. Chem. Phys, 98, 11623–11627, 1994.
  • [18] C. Lee, W. Yang, R.G. Parr, ''Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density,'' Phys. Rev. B, 37, 785–789, 1988.
There are 18 citations in total.

Details

Primary Language English
Subjects Chemical Engineering
Journal Section Makaleler
Authors

Shahodat Irmumınova 0000-0001-6896-4197

Barış Sezgin 0000-0001-5359-4488

Tahir Tilki 0000-0002-1040-2375

Project Number FYL-2019-7399
Publication Date November 29, 2020
Published in Issue Year 2020

Cite

IEEE S. Irmumınova, B. Sezgin, and T. Tilki, “Novel Heterocyclic Azo Compounds: Synthesis, Characterization and DFT Calculations”, Süleyman Demirel University Faculty of Arts and Science Journal of Science, vol. 15, no. 2, pp. 319–329, 2020, doi: 10.29233/sdufeffd.820455.