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Synthesis and Characterization of Bisindandione Derivative Azo Dye, Experimental and Theoretical Investigation of Its Tautomeric Properties

Year 2020, Volume: 16 Issue: 1, 61 - 67, 27.03.2020

Abstract

In this study, the synthesis, characterization, and tautomeric properties of 2,2'-bis(phenylazo)-5,5'-biindane-1,1',3,3'-tetrone, a new bisindandione derivative, were investigated. 2,2'-Bis(phenylazo)-5,5'-biindane-1,1',3,3'-tetrone was obtained after the diazo coupling reactions between [5,5'-biindane]-1,1',3,3'-tetrone and aniline, and characterized by FT-IR, 1H NMR and MS. The structural and spectroscopic analyses of azo dye were examined using Density Function Theory and vibration frequencies calculated with the optimized structure were compared with experimental data. The obtained data showed that the hydrazo form was dominant for 2,2'-bis(phenylazo)-5,5'-biindane-1,1',3,3'-tetrone.

References

  • Joullié, MM, Thompson, TR, Nemeroff NH. 1991. Ninhydrin and ninhydrin analogs. Syntheses and applications. Tetrahedron; 47 (42): 8791-8830.
  • Ruhemann, S. 1996. CXXXII.-Cyclic di- and tri-ketones. Journal of the Chemical Society Transactions; 97: 1438-1449.
  • Khan, Z, Rafiquee, ZA, Khan, AA. 1996. Effect of Temperature, pH, Hydrindantin, Ascorbic Acid and Organic Solvents in the Colorimetric Estimation of a-Amino Acids with Ninhydrin. Journal of the Indian Chemical Society; 73 (6): 305-306.
  • Dietz, F, Rommel-Möhle, K, Schleitzer, A, Tyutyulkov, N. 1993. On the Chromophore of the Ninhydrin-Amino Acid Color Reaction. Zeitschrift für Naturforschung B A Journal of Chemical Sciences; 48 (8): 1133-1137.
  • Hark, RR, Hauze, DB, Petrovskais, O, Joullié, MM. 2001. Synthetic studies of novel ninhydrin analogs. Canadian Journal of Chemistry; 79:1632-1654.
  • Leblois, D, Piessard, S, Le Baut, G, Kumar, P, Brion, JD, Sparfel, L, Sanchez, RY, Juge, M, Petit, JY, Welin, L. 1987. Pyrophthalones VII. Synthesis and anti-inflammatory activity of 2-(4-pyridinyl)indane-1,3-diones diversely substituted on the benzene ring. European Journal of Medicinal Chemistry; 22 (3): 229-238.
  • Hansen, DB, Joullié, MM. 2005. The development of novel ninhydrin analogues. Chemical Society Review; 34: 408-417.
  • Bello, KA, Cheng, L, Griffiths, J. 1987. Perkin Transactions 2 Near-infrared absorbing methine dyes based on dicyanovinyl derivatives of indane-1,3-dione. Journal of the Chemical Society; 6: 815-818.
  • Li, X, Kim, SH, Son, YA. 2009. Optical properties of donor-π-(acceptor)n merocyanine dyes with dicyanovinylindane as acceptor group and triphenylamine as donor unit. Dyes and Pigments; 82: 293-298.
  • Hansen, DB, Joulie, MM. 2005. The development of novel ninhydrin analogues. Chemical Society Reviews; 34: 408-417.
  • Bryce, MR, Davies, SR, Hasan, M, Ashwell GJ, Szablewski, M, Drew, MGB, Short, R, Hursthouse, MB. 1989. Preparation and magnetic properties of a range of metal and organic cation salts of 2,3-dicyano-1,4-naphthoquinone (DCNQ). X-Ray crystal structure of (methyltriphenylphosphonium)1(DCNQ)1(H2O)1 and 2-dicyanomethylene-indan-1,3-dione (DCID). The rearrangement of DCID to DCNQ. Journal of the Chemical Society, Perkin Transactions 2; 9:1285-1292.
  • Seniutinas, G, Tomasiunas, R, Czaplicki, R, Sahraoui, B, Daskeviciene, M, Getautis, V, Balevicius, Z. 2012. Arylmethylene-1,3-indandione based molecular glasses: third order optical non-linearity. Dyes and Pigments; 95: 33-40.
  • Sarvesh, PK, Nizamuddin, K. 2008. Synthesis and Antimicrobial Study of Novel 1-Aryl-2-oxo- indano[3,2-d]pyrido/pyrimido[1,2-b]pyrimidines. Archiv der Pharmazie - Chemistry in Life Sciences; 341: 418-423.
  • Heravi, MM, Hosseini, T, Derikvand, F, Beheshtiha, SYS, Bamoharram, FF. 2010. H6P2W18O62·18H2O-Catalyzed, Three- Component, One-Pot Synthesis of Indeno[1,2-b]quinoline-7-one Derivatives. Synthetic Communications; 40: 2402-2406.
  • Ahmedova, A, Atanasov, V, Marinova, P, Stoyanov, N, Mitewa, M. 2009. Synthesis, characterization and spectroscopic properties of some 2-substituted 1,3-indandiones and their metal complexes. Central European Journal of Chemistry; 7 (3): 429-438.
  • Ahmedova, A, Marinova, P, Ciattini, S, Stoyanov, N, Springborg, M, Mitewa, M. 2009. A combined experimental and theoretical approach for structural study on a new cinnamoyl derivative of 2-acetyl-1,3-indandione and its metal(II) complexes. Journal of Structural Chemistry; 20: 101-111.
  • Riahi, S, Ganjali, MR, Moghaddam, AB, Norouzi, P, Saied Saeed Hosseiny Davarani, SSH. 2008. Structural study of 2-(1-oxo-1 H-inden-3-yl)-2H-indene-1,3-dione by DFT calculations, NMR and IR spectroscopy. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy; 70: 94-98.
  • Gulbinas, V, Karpicz, R, Muzikante, I, Valkunas, L. 2010. Fluorescence quenching by trapped charge carriers in N,N-dimethylaminobenzylidene 1,3-indandione films. Thin Solid Films; 518: 3299–3304.
  • Ozalina, V, Neilands, O. 1971. Analogs of 2-methoxycarbonyl-1,3-indandione in the diphenyl and diphenyl oxide series. Latvijas PSR Zinatnu Akademijas Vestis, Kimijas Serija; 2: 235-240.
  • Çelik Erbaş, S, Gülle, S. 2018. Synthesis and photophysical behaviours of novel phenanthro[9,10-d] imidazole substituted azo dyes in solvent media. Celal Bayar University Journal of Science; 14: 285-289.
  • El-Shishtawy, RM, Borbone, F, Al-amshany, ZM, Tuzi, A, Barsella, A, Asiri, AM, Roviello, A. 2013. Thiazole azo dyes with lateral donor branch: Synthesis, structure and second order NLO properties. Dyes and Pigments; 96: 45-51.
  • Kinali, S, Demirci, S, Calisir, Z, Kurt, M, Atac, A. 2011. DFT, FT-IR, FT-Raman and NMR studies of 4-(substituted phenylazo)-3,5-diacetamido-1H-pyrazoles. Journal of Molecular Structure; 993(1-3): 254-258.
  • Kinali-Demirci, S, Demirci, S, Kurt, M. 2013. Synthesis, structure characterization and antimicrobial evaluation of 4-(substituted phenylazo)-3,5-diacetamido-1H-pyrazoles. Spectrachimica Acta-Part A: Molecular and Biomolecular Spectroscopy; 106: 12-18.
  • Catino, SC, Farris, RE. Azo dyes. In: Grayson M (ed) Concise encyclopedia of chemical technology. John Wiley and Sons, New York, 1985, pp 142-144.
  • Zollinger, H. Color chemistry: Synthesis, properties and applications of organic dyes and pigments, 3rd, revised edition Wiley-VCH, 2003.
  • Kim, JP, Kim, JS, Park, JS, Jang, SS, Lee, JJ. 2016. Synthesis of temporarily solubilised azo disperse dyes containing a ß-sulphatoethylsulphonyl group and dispersant-free dyeing of polyethylene terephthalate fabric. Coloration Technology; 132: 368-375.
  • Mungmeechai, T, Jantip, S, Suwanruji, P. 2010. Study of the relationships between the chemical structures of azo disperse dyes and their dyeing properties on polyester. Advanced Materials Research; 93-94: 332-335.
  • Pazarbaşı, MB, Karaboz, İ, Koçyiğit, A, Özdemir, G, Yaşa, İ. 2011. The use of Pleurotus ostreatus MCC07 strain in decolorization of various dyes used in leather industry. Celal Bayar University Journal of Science; 7: 21-30.
  • Gaussian 09, Revision A.1, Frisch, MJ, Trucks, GW, Schlegel, HB, Scuseria, GE, Robb, MA, Cheeseman, JR, Scalmani, G, Barone, V, Mennucci, B, Petersson, GA, Nakatsuji, H, Caricato, M, Li, X, Hratchian, HP, Izmaylov, J. Bloino, AF, Zheng, G, Sonnenberg, JL, Hada, M, Ehara, M, Toyota, K, Fukuda, R, Hasegawa, J, Ishida, M, Nakajima, T, Honda, Y, Kitao, O, Nakai, H, Vreven, T, Montgomery Jr., JA, Peralta, JE, Ogliaro, F, Bearpark, M, Heyd, JJ, Brothers, E, Kudin, KN, Staroverov, VN, Kobayashi, R, Normand, J, Raghavachari, K, Rendell, A, Burant, JC, Iyengar, SS, Tomasi, J, Cossi, M, Rega, N, Millam, JM, Klene, M, Knox, JE, Cross, JB, Bakken, V, Adamo, C, Jaramillo, J, Gomperts, R, Stratmann, RE, Yazyev, O, Austin, AJ, Cammi, R, Pomelli, C, Ochterski, JW, Martin, RL, Morokuma, K, Zakrzewski, VG, Voth, GA, Salvador, P, Dannenberg, JJ, Dapprich, S, Daniels, AD, Farkas, O, Foresman, JB, Ortiz, JV, Cioslowski, J, Fox, DJ. Gaussian, Inc., Wallingford CT, 2009
  • Dennington, R, Keith, T, Millam, J. GaussView, Version 5 Semichem Inc., Shawnee Mission KS, 2009.
  • Vural, H, İdil, Ö. 2019. Synthesis, spectroscopic investigation and biological activities of copper(II) complex of 2-(2,4-difluorophenyl)pyridine: A combined theoretical and experimental study. Journal of Molecular Structure; 1177: 242-248.
  • Ajaz, M, Rehman, A, Khan, Z, Nisar, MA, Hussain, S. 2019. Degradation of azo dyes by Alcaligenes aquatilis 3c and its potential use in the wastewater treatment. AMB Express; 9: 64.
  • Snehalatha, M, Ravikumar, C, Joe, IH, Sekar, N, Jayakumar, VS. 2009. Spectroscopic analysis and DFT calculations of a food additive Carmoisine. Spectrachimica Acta-Part A: Molecular and Biomolecular Spectroscopy; 72: 654-662.
Year 2020, Volume: 16 Issue: 1, 61 - 67, 27.03.2020

Abstract

References

  • Joullié, MM, Thompson, TR, Nemeroff NH. 1991. Ninhydrin and ninhydrin analogs. Syntheses and applications. Tetrahedron; 47 (42): 8791-8830.
  • Ruhemann, S. 1996. CXXXII.-Cyclic di- and tri-ketones. Journal of the Chemical Society Transactions; 97: 1438-1449.
  • Khan, Z, Rafiquee, ZA, Khan, AA. 1996. Effect of Temperature, pH, Hydrindantin, Ascorbic Acid and Organic Solvents in the Colorimetric Estimation of a-Amino Acids with Ninhydrin. Journal of the Indian Chemical Society; 73 (6): 305-306.
  • Dietz, F, Rommel-Möhle, K, Schleitzer, A, Tyutyulkov, N. 1993. On the Chromophore of the Ninhydrin-Amino Acid Color Reaction. Zeitschrift für Naturforschung B A Journal of Chemical Sciences; 48 (8): 1133-1137.
  • Hark, RR, Hauze, DB, Petrovskais, O, Joullié, MM. 2001. Synthetic studies of novel ninhydrin analogs. Canadian Journal of Chemistry; 79:1632-1654.
  • Leblois, D, Piessard, S, Le Baut, G, Kumar, P, Brion, JD, Sparfel, L, Sanchez, RY, Juge, M, Petit, JY, Welin, L. 1987. Pyrophthalones VII. Synthesis and anti-inflammatory activity of 2-(4-pyridinyl)indane-1,3-diones diversely substituted on the benzene ring. European Journal of Medicinal Chemistry; 22 (3): 229-238.
  • Hansen, DB, Joullié, MM. 2005. The development of novel ninhydrin analogues. Chemical Society Review; 34: 408-417.
  • Bello, KA, Cheng, L, Griffiths, J. 1987. Perkin Transactions 2 Near-infrared absorbing methine dyes based on dicyanovinyl derivatives of indane-1,3-dione. Journal of the Chemical Society; 6: 815-818.
  • Li, X, Kim, SH, Son, YA. 2009. Optical properties of donor-π-(acceptor)n merocyanine dyes with dicyanovinylindane as acceptor group and triphenylamine as donor unit. Dyes and Pigments; 82: 293-298.
  • Hansen, DB, Joulie, MM. 2005. The development of novel ninhydrin analogues. Chemical Society Reviews; 34: 408-417.
  • Bryce, MR, Davies, SR, Hasan, M, Ashwell GJ, Szablewski, M, Drew, MGB, Short, R, Hursthouse, MB. 1989. Preparation and magnetic properties of a range of metal and organic cation salts of 2,3-dicyano-1,4-naphthoquinone (DCNQ). X-Ray crystal structure of (methyltriphenylphosphonium)1(DCNQ)1(H2O)1 and 2-dicyanomethylene-indan-1,3-dione (DCID). The rearrangement of DCID to DCNQ. Journal of the Chemical Society, Perkin Transactions 2; 9:1285-1292.
  • Seniutinas, G, Tomasiunas, R, Czaplicki, R, Sahraoui, B, Daskeviciene, M, Getautis, V, Balevicius, Z. 2012. Arylmethylene-1,3-indandione based molecular glasses: third order optical non-linearity. Dyes and Pigments; 95: 33-40.
  • Sarvesh, PK, Nizamuddin, K. 2008. Synthesis and Antimicrobial Study of Novel 1-Aryl-2-oxo- indano[3,2-d]pyrido/pyrimido[1,2-b]pyrimidines. Archiv der Pharmazie - Chemistry in Life Sciences; 341: 418-423.
  • Heravi, MM, Hosseini, T, Derikvand, F, Beheshtiha, SYS, Bamoharram, FF. 2010. H6P2W18O62·18H2O-Catalyzed, Three- Component, One-Pot Synthesis of Indeno[1,2-b]quinoline-7-one Derivatives. Synthetic Communications; 40: 2402-2406.
  • Ahmedova, A, Atanasov, V, Marinova, P, Stoyanov, N, Mitewa, M. 2009. Synthesis, characterization and spectroscopic properties of some 2-substituted 1,3-indandiones and their metal complexes. Central European Journal of Chemistry; 7 (3): 429-438.
  • Ahmedova, A, Marinova, P, Ciattini, S, Stoyanov, N, Springborg, M, Mitewa, M. 2009. A combined experimental and theoretical approach for structural study on a new cinnamoyl derivative of 2-acetyl-1,3-indandione and its metal(II) complexes. Journal of Structural Chemistry; 20: 101-111.
  • Riahi, S, Ganjali, MR, Moghaddam, AB, Norouzi, P, Saied Saeed Hosseiny Davarani, SSH. 2008. Structural study of 2-(1-oxo-1 H-inden-3-yl)-2H-indene-1,3-dione by DFT calculations, NMR and IR spectroscopy. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy; 70: 94-98.
  • Gulbinas, V, Karpicz, R, Muzikante, I, Valkunas, L. 2010. Fluorescence quenching by trapped charge carriers in N,N-dimethylaminobenzylidene 1,3-indandione films. Thin Solid Films; 518: 3299–3304.
  • Ozalina, V, Neilands, O. 1971. Analogs of 2-methoxycarbonyl-1,3-indandione in the diphenyl and diphenyl oxide series. Latvijas PSR Zinatnu Akademijas Vestis, Kimijas Serija; 2: 235-240.
  • Çelik Erbaş, S, Gülle, S. 2018. Synthesis and photophysical behaviours of novel phenanthro[9,10-d] imidazole substituted azo dyes in solvent media. Celal Bayar University Journal of Science; 14: 285-289.
  • El-Shishtawy, RM, Borbone, F, Al-amshany, ZM, Tuzi, A, Barsella, A, Asiri, AM, Roviello, A. 2013. Thiazole azo dyes with lateral donor branch: Synthesis, structure and second order NLO properties. Dyes and Pigments; 96: 45-51.
  • Kinali, S, Demirci, S, Calisir, Z, Kurt, M, Atac, A. 2011. DFT, FT-IR, FT-Raman and NMR studies of 4-(substituted phenylazo)-3,5-diacetamido-1H-pyrazoles. Journal of Molecular Structure; 993(1-3): 254-258.
  • Kinali-Demirci, S, Demirci, S, Kurt, M. 2013. Synthesis, structure characterization and antimicrobial evaluation of 4-(substituted phenylazo)-3,5-diacetamido-1H-pyrazoles. Spectrachimica Acta-Part A: Molecular and Biomolecular Spectroscopy; 106: 12-18.
  • Catino, SC, Farris, RE. Azo dyes. In: Grayson M (ed) Concise encyclopedia of chemical technology. John Wiley and Sons, New York, 1985, pp 142-144.
  • Zollinger, H. Color chemistry: Synthesis, properties and applications of organic dyes and pigments, 3rd, revised edition Wiley-VCH, 2003.
  • Kim, JP, Kim, JS, Park, JS, Jang, SS, Lee, JJ. 2016. Synthesis of temporarily solubilised azo disperse dyes containing a ß-sulphatoethylsulphonyl group and dispersant-free dyeing of polyethylene terephthalate fabric. Coloration Technology; 132: 368-375.
  • Mungmeechai, T, Jantip, S, Suwanruji, P. 2010. Study of the relationships between the chemical structures of azo disperse dyes and their dyeing properties on polyester. Advanced Materials Research; 93-94: 332-335.
  • Pazarbaşı, MB, Karaboz, İ, Koçyiğit, A, Özdemir, G, Yaşa, İ. 2011. The use of Pleurotus ostreatus MCC07 strain in decolorization of various dyes used in leather industry. Celal Bayar University Journal of Science; 7: 21-30.
  • Gaussian 09, Revision A.1, Frisch, MJ, Trucks, GW, Schlegel, HB, Scuseria, GE, Robb, MA, Cheeseman, JR, Scalmani, G, Barone, V, Mennucci, B, Petersson, GA, Nakatsuji, H, Caricato, M, Li, X, Hratchian, HP, Izmaylov, J. Bloino, AF, Zheng, G, Sonnenberg, JL, Hada, M, Ehara, M, Toyota, K, Fukuda, R, Hasegawa, J, Ishida, M, Nakajima, T, Honda, Y, Kitao, O, Nakai, H, Vreven, T, Montgomery Jr., JA, Peralta, JE, Ogliaro, F, Bearpark, M, Heyd, JJ, Brothers, E, Kudin, KN, Staroverov, VN, Kobayashi, R, Normand, J, Raghavachari, K, Rendell, A, Burant, JC, Iyengar, SS, Tomasi, J, Cossi, M, Rega, N, Millam, JM, Klene, M, Knox, JE, Cross, JB, Bakken, V, Adamo, C, Jaramillo, J, Gomperts, R, Stratmann, RE, Yazyev, O, Austin, AJ, Cammi, R, Pomelli, C, Ochterski, JW, Martin, RL, Morokuma, K, Zakrzewski, VG, Voth, GA, Salvador, P, Dannenberg, JJ, Dapprich, S, Daniels, AD, Farkas, O, Foresman, JB, Ortiz, JV, Cioslowski, J, Fox, DJ. Gaussian, Inc., Wallingford CT, 2009
  • Dennington, R, Keith, T, Millam, J. GaussView, Version 5 Semichem Inc., Shawnee Mission KS, 2009.
  • Vural, H, İdil, Ö. 2019. Synthesis, spectroscopic investigation and biological activities of copper(II) complex of 2-(2,4-difluorophenyl)pyridine: A combined theoretical and experimental study. Journal of Molecular Structure; 1177: 242-248.
  • Ajaz, M, Rehman, A, Khan, Z, Nisar, MA, Hussain, S. 2019. Degradation of azo dyes by Alcaligenes aquatilis 3c and its potential use in the wastewater treatment. AMB Express; 9: 64.
  • Snehalatha, M, Ravikumar, C, Joe, IH, Sekar, N, Jayakumar, VS. 2009. Spectroscopic analysis and DFT calculations of a food additive Carmoisine. Spectrachimica Acta-Part A: Molecular and Biomolecular Spectroscopy; 72: 654-662.
There are 33 citations in total.

Details

Primary Language English
Subjects Engineering
Journal Section Articles
Authors

Selin Kınalı Demirci

Publication Date March 27, 2020
Published in Issue Year 2020 Volume: 16 Issue: 1

Cite

APA Kınalı Demirci, S. (2020). Synthesis and Characterization of Bisindandione Derivative Azo Dye, Experimental and Theoretical Investigation of Its Tautomeric Properties. Celal Bayar University Journal of Science, 16(1), 61-67.
AMA Kınalı Demirci S. Synthesis and Characterization of Bisindandione Derivative Azo Dye, Experimental and Theoretical Investigation of Its Tautomeric Properties. CBUJOS. March 2020;16(1):61-67.
Chicago Kınalı Demirci, Selin. “Synthesis and Characterization of Bisindandione Derivative Azo Dye, Experimental and Theoretical Investigation of Its Tautomeric Properties”. Celal Bayar University Journal of Science 16, no. 1 (March 2020): 61-67.
EndNote Kınalı Demirci S (March 1, 2020) Synthesis and Characterization of Bisindandione Derivative Azo Dye, Experimental and Theoretical Investigation of Its Tautomeric Properties. Celal Bayar University Journal of Science 16 1 61–67.
IEEE S. Kınalı Demirci, “Synthesis and Characterization of Bisindandione Derivative Azo Dye, Experimental and Theoretical Investigation of Its Tautomeric Properties”, CBUJOS, vol. 16, no. 1, pp. 61–67, 2020.
ISNAD Kınalı Demirci, Selin. “Synthesis and Characterization of Bisindandione Derivative Azo Dye, Experimental and Theoretical Investigation of Its Tautomeric Properties”. Celal Bayar University Journal of Science 16/1 (March 2020), 61-67.
JAMA Kınalı Demirci S. Synthesis and Characterization of Bisindandione Derivative Azo Dye, Experimental and Theoretical Investigation of Its Tautomeric Properties. CBUJOS. 2020;16:61–67.
MLA Kınalı Demirci, Selin. “Synthesis and Characterization of Bisindandione Derivative Azo Dye, Experimental and Theoretical Investigation of Its Tautomeric Properties”. Celal Bayar University Journal of Science, vol. 16, no. 1, 2020, pp. 61-67.
Vancouver Kınalı Demirci S. Synthesis and Characterization of Bisindandione Derivative Azo Dye, Experimental and Theoretical Investigation of Its Tautomeric Properties. CBUJOS. 2020;16(1):61-7.