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FENOLFTALEİN TABANLI FLORESANS SENSÖR SENTEZİ VE SULU ORTAMDA AĞIR METALLERE KARŞI OPTİK ÖZELLİKLERİNİN İNCELENMESİ

Year 2021, Volume: 9 , 187 - 199, 30.12.2021
https://doi.org/10.36306/konjes.983194

Abstract

Bu çalışmada (R)-(-)-2-fenilglisinol ile türevlendirilmiş fenolftalein tabanlı ligand L bileşiği sentezlendi ve yapısı 1H-NMR ve FTIR spektroskopisi ile karakterize edildi. Hazırlanan fenolftalein tabanlı ligand L’nin farklı katyonlara karşı optik özellikleri etanol-su (95/5; v/v) ortamında floresans ve UV-GB spektroskopisi ile incelendi. Ligand L’nin Zn2+ katyonuna karşı diğer katyonlara göre 454 nm’de şiddetli, seçimli ve hassas bir floresans özelliği gösterdiği belirlendi. Ligand L’nin Zn2+ ile kompleksleşme mekanizması, ICT ve C=N izomerizasyonunun engellenmesi ve kompleksleşme ile açıklandı. Ligand L ile Zn2+ katyonu arasında floresans titrasyon çalışması gerçekleştirildi ve gerekli sensör parametreleri incelendi. Job grafiğine göre, kompleksleşme oranı 1:2 olarak belirlendi. Bağlanma sabiti Benesi-Hildebrand denklemine göre 1,72x1012 (logK= 12,24) olarak hesaplandı. Limit algılama değeri 118 nM olarak hesaplandı. Tüm veriler incelendiğinde, hazırlanan fenolftalein tabanlı ligand L’nin Zn2+ katyonuna karşı seçimli ve hassas floresans sensör özellikleri gösterdiği belirlendi.

References

  • Alici, O, Aydin, D, 2021 “A Schiff-base receptor based on phenolphthalein derivate appended 2-furoic hydrazide: Highly sensitive fluorogenic “turn on” chemosensor for Al3+”, Journal of Photochemistry and Photobiology A: Chemistry, vol. 404, pp. 112876.
  • Bie, F., Cao, H., Yan, P., Cui, H., Shi, Y., Ma, J, Liu, X., Han, Y., 2020, “A cyanobiphenyl-based ratiometric fluorescent sensor for highly selective and sensitive detection of Zn2+”, Inorganica Chimica Acta, vol. 508, pp. 119652.
  • Erdemir, S., Kocyigit, O., 2017, “A novel dye based on phenolphthalein-fluorescein as a fluorescent probe for the dual-channel detection of Hg2+ and Zn2+”, Dyes and Pigments, vol. 145, pp. 72 – 79.
  • Erdemir, S., Kocyigit, O., 2018, “Dual recognition of Zn2+ and Al3+ ions by a novel probe containing two fluorophore through different signaling mechanisms”, Sensors and Actuators B: Chemical, vol. 273, pp 56 – 61.
  • Erdemir, S., Malkondu, S., 2019, “Dual-emmisive fluorescent probe based on phenolphthalein appended diaminomaleonitrile for Al3+ and the colorimetric recognition of Cu2+” Dyes and Pigments, vol 163, pp 330 – 336.
  • Erdemir, S., Malkondu, S., Kocyigit, O., 2019, “A reversible calix[4]arene armed phenolphthalein based fluorescent probe for the detection of Zn2+ and an application in living cells”, The Journal of Biological and Chemical Luminescence, vol. 34, pp. 106 – 112.
  • Erdemir, S., Tabakci, B., 2017, “Selective and Sensitive Fluorescein-Benzothiazole Based Fluorescent Sensor for Zn2+ Ion in Aqueous Media”, Journal of Fluorescence, vol. 27, pp. 2145 – 2152.
  • Erdemir, S., Tabakci, B., 2018, “Highly sensitive fluorometric detection of Zn2+ ion by calix[4]arene derivative appended 4-biphenylcarbonitrile”, Dyes and Pigments, vol. 151, pp. 116 – 122.
  • Fu, J., Chang, Y., Li, B., Wang, X., Xie, X., Xu, K., 2020, “A dual fluorescence probe for Zn2+ and Al3+ through differentially response and bioimazing in living cells”, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, vol. 225, pp 117493.
  • Helal, A., Rashid, M. H., Choi, C., Kim, H. 2021, “New regioisomeric naphthol-substituted thiazole based ratiometric fluorescence sensor for Zn2+ with a remarkable red shift in emission spectra”, Tetrahedron, vol. 68, pp. 647 – 653.
  • Hojitsiriyanont, J., Chaibuth, P., Boonkitpatarakul, K., Ruangpornvisuti, V., Palaga, T., Chainok, K., Sukwattanasinitt, M., 2021, “Effects of amino proton and denticity of quinolone-pyridine based dyes on Cd2+ and Zn2+ fluorescence sensing properties”, Journal of Photochemistry & Photobiology A: Chemistry, vol. 415, pp. 113307.
  • Jimenez-Sanchez, A., Ortiz, B., Navarrete, V. O., Flores, J. C., Farfan, N., Santillan, R., 2015, “A dual-model fluorescent Zn2+/Cu2+ ions sensor with in-situ detection of S2-/(PO4)- and colorimetric detection of Fe 2+ ion”, Inorganica Chimica Acta, vol 429, pp 243 – 251.
  • Joseph, R., Ramanujam, B., Pal, H., Rao, C. P., 2008, “Lower rim 1,3-di-amide-derivative of calix[4]arene possessing bis-{N-(2,2’-dipyridylamide)} pendants: a dual fluorescence sensor for Zn2+ and Ni2+”, Tetrahedron Letters, vol 49, pp 6257 – 6261.
  • Liu, J., Meng, X., Duan, H., Xu, T., Ding, Z., Liu, Y., Lucia, L. 2016, “Two Schiff-base fluorescence probes based on triazole and benzotriazole for selective detection of Zn2+”, Sensors and Actuators B: Chemical, vol 227, pp 296 – 303.
  • Maity, D., Mukherjee, A., Mandal, S. K., Roy, P., 2019, “Modulation of fluorescence sensing properties of quinolone-based chemosensor for Zn2+: Application in cell imaging studies”, Journal of Luminescence, vol. 210, pp 508 – 518.
  • Nunes, M. C., Carlos, F. d. S., Fuganti, O., Galindo, D. D. M., De Boni, L., Abate, G., Nunes, F. S., 2020, “Turn-on fluorescence study of a highly selective acridine-based chemosensor for Zn2+ in aqueous solutions”, Inorganica Chimica Acta, vol. 499, pp. 119191.
  • Park, G. J., Lee, M. M., You, G. R., Choi, Y. W., Kim, C., 2014, “A turn-on and reversible fluorescence sensor with high affinity to Zn2+ in aqueous solution”, Tetrahedron Letters, vol. 55, pp. 2517 – 2522.
  • Rajasekaran, D., Venkatachalam, K., Periasamy, V., 2020, “A bisphenol based fluorescence chemosensor for the selective detection of Zn2+ and PPi ions and its bioluminescence imaging”, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, vol. 242, pp 118730.
  • Roy, N., Dutta, A., Mondal, P., Paul, P. C., Singh, T. S., 2016, “A new coumarin based dual functional chemosensor for colorimetric detection of Fe3+ and fluorescence turn-on responde of Zn2+”, Sensors and Actuators B: Chemical, vol 236, pp 719 – 731.
  • Sasaki, H., Hanaoka, K., Urano, Y., Terai, T., Nagano, T., 2011, “Design and synthesis of a novel fluorescence probe for Zn2+ based on the spirolactam ring-opening process of rhodamine derivatives”, Bioorganic & Medicinal Chemistry, vol.19, pp 1072 – 1078.
  • Shao, Y. ve diğ., 2015, “Advances in molecular quantum chemistry contained in the Q-Chem 4 program package”, Molecular Physics, vol. 113, pp. 184-215.
  • Tabakci B., Ahmed, H. M. A., Erdemir, S., 2019, “Fast and Reversible “Turn on” Fluorescent Sensors Based on Bisphenol-a for Zn2+ in Aqueous Solution”, Journal of Fluorescence, vol. 29, pp. 1049 – 1087.
  • Venkatesan, V., R. Kumar, S., Kumar, S. K. A., Sahoo, S. K., 2019, “Highly selective turn-on fluorogenic chemosensor for Zn2+ based on chelation enhanced fluorescence”, Inorganic Chemistry Communications, vol. 102, pp. 171 – 179.
  • Wang, R., Wang, N., Tu, Y., Liu, G., Pu, S., 2018, “A new fluorescence based on diarylethene with a N’-(quinolin-8-ylmethylene)benzohydrazide group for Zn2+ detection”, Journal of Photochemistry & Photobiology A: Chemistry, vol. 364, pp. 32 – 39.
  • Xu, T., Duan, H., Wang, X., Meng, X., Bu, J., 2015, “Fluorescence sensors for Zn2+ based on conjugated indole Schiff base”, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, vol. 138, pp 603 – 608.
  • Zhu, J., Zhang, Y., Chen, Y., Sun, T., Tang, Y., Huang, Y., Yang, Q., Ma, D., Wang, Y., Wang, M., 2017, “A Schiff base fluorescence probe for highly selective turn-on recognition of Zn2+”, Tetrahedron Letters, vol. 58, pp. 365 – 370.

Synthesis of Phenolphtalein-Based Fluorescence Sensor and Investigation of Its Optical Properties Towards Heavy Metals in Aqueous Media

Year 2021, Volume: 9 , 187 - 199, 30.12.2021
https://doi.org/10.36306/konjes.983194

Abstract

In this study, phenolphthalein-based ligand L compound derivatized with R-2-phenylglycinol was synthesized and its structure was characterized by 1H-NMR and FTIR spectroscopy. Optical properties of the prepared phenolphthalein-based ligand L towards different cations were investigated by fluorescence and UV-VIS spectroscopy in ethanol-water (95/5; v/v) medium. It was determined that ligand L showed a strong, selective and sensitive fluorescence at 454 nm towards the Zn2+ cation compared to other cations. The mechanism of ligand L complexing with Zn2+ was explained by ICT and inhibition of C=N isomerization and complexation. Fluorescence titration study was performed between ligand L and Zn2+ cation and necessary sensor parameters were examined. According to the Job plot, the complexing ratio was determined as 1:2. The binding constant was calculated as 1.72 x 1012 (logK= 12.24) according to the Benesi-Hildebrand equation. The limit detection value was calculated as 118 nM. When all data were examined, it was determined that the prepared phenolphthalein-based ligand L showed selective and sensitive fluorescence sensor properties against Zn2+ cation.

References

  • Alici, O, Aydin, D, 2021 “A Schiff-base receptor based on phenolphthalein derivate appended 2-furoic hydrazide: Highly sensitive fluorogenic “turn on” chemosensor for Al3+”, Journal of Photochemistry and Photobiology A: Chemistry, vol. 404, pp. 112876.
  • Bie, F., Cao, H., Yan, P., Cui, H., Shi, Y., Ma, J, Liu, X., Han, Y., 2020, “A cyanobiphenyl-based ratiometric fluorescent sensor for highly selective and sensitive detection of Zn2+”, Inorganica Chimica Acta, vol. 508, pp. 119652.
  • Erdemir, S., Kocyigit, O., 2017, “A novel dye based on phenolphthalein-fluorescein as a fluorescent probe for the dual-channel detection of Hg2+ and Zn2+”, Dyes and Pigments, vol. 145, pp. 72 – 79.
  • Erdemir, S., Kocyigit, O., 2018, “Dual recognition of Zn2+ and Al3+ ions by a novel probe containing two fluorophore through different signaling mechanisms”, Sensors and Actuators B: Chemical, vol. 273, pp 56 – 61.
  • Erdemir, S., Malkondu, S., 2019, “Dual-emmisive fluorescent probe based on phenolphthalein appended diaminomaleonitrile for Al3+ and the colorimetric recognition of Cu2+” Dyes and Pigments, vol 163, pp 330 – 336.
  • Erdemir, S., Malkondu, S., Kocyigit, O., 2019, “A reversible calix[4]arene armed phenolphthalein based fluorescent probe for the detection of Zn2+ and an application in living cells”, The Journal of Biological and Chemical Luminescence, vol. 34, pp. 106 – 112.
  • Erdemir, S., Tabakci, B., 2017, “Selective and Sensitive Fluorescein-Benzothiazole Based Fluorescent Sensor for Zn2+ Ion in Aqueous Media”, Journal of Fluorescence, vol. 27, pp. 2145 – 2152.
  • Erdemir, S., Tabakci, B., 2018, “Highly sensitive fluorometric detection of Zn2+ ion by calix[4]arene derivative appended 4-biphenylcarbonitrile”, Dyes and Pigments, vol. 151, pp. 116 – 122.
  • Fu, J., Chang, Y., Li, B., Wang, X., Xie, X., Xu, K., 2020, “A dual fluorescence probe for Zn2+ and Al3+ through differentially response and bioimazing in living cells”, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, vol. 225, pp 117493.
  • Helal, A., Rashid, M. H., Choi, C., Kim, H. 2021, “New regioisomeric naphthol-substituted thiazole based ratiometric fluorescence sensor for Zn2+ with a remarkable red shift in emission spectra”, Tetrahedron, vol. 68, pp. 647 – 653.
  • Hojitsiriyanont, J., Chaibuth, P., Boonkitpatarakul, K., Ruangpornvisuti, V., Palaga, T., Chainok, K., Sukwattanasinitt, M., 2021, “Effects of amino proton and denticity of quinolone-pyridine based dyes on Cd2+ and Zn2+ fluorescence sensing properties”, Journal of Photochemistry & Photobiology A: Chemistry, vol. 415, pp. 113307.
  • Jimenez-Sanchez, A., Ortiz, B., Navarrete, V. O., Flores, J. C., Farfan, N., Santillan, R., 2015, “A dual-model fluorescent Zn2+/Cu2+ ions sensor with in-situ detection of S2-/(PO4)- and colorimetric detection of Fe 2+ ion”, Inorganica Chimica Acta, vol 429, pp 243 – 251.
  • Joseph, R., Ramanujam, B., Pal, H., Rao, C. P., 2008, “Lower rim 1,3-di-amide-derivative of calix[4]arene possessing bis-{N-(2,2’-dipyridylamide)} pendants: a dual fluorescence sensor for Zn2+ and Ni2+”, Tetrahedron Letters, vol 49, pp 6257 – 6261.
  • Liu, J., Meng, X., Duan, H., Xu, T., Ding, Z., Liu, Y., Lucia, L. 2016, “Two Schiff-base fluorescence probes based on triazole and benzotriazole for selective detection of Zn2+”, Sensors and Actuators B: Chemical, vol 227, pp 296 – 303.
  • Maity, D., Mukherjee, A., Mandal, S. K., Roy, P., 2019, “Modulation of fluorescence sensing properties of quinolone-based chemosensor for Zn2+: Application in cell imaging studies”, Journal of Luminescence, vol. 210, pp 508 – 518.
  • Nunes, M. C., Carlos, F. d. S., Fuganti, O., Galindo, D. D. M., De Boni, L., Abate, G., Nunes, F. S., 2020, “Turn-on fluorescence study of a highly selective acridine-based chemosensor for Zn2+ in aqueous solutions”, Inorganica Chimica Acta, vol. 499, pp. 119191.
  • Park, G. J., Lee, M. M., You, G. R., Choi, Y. W., Kim, C., 2014, “A turn-on and reversible fluorescence sensor with high affinity to Zn2+ in aqueous solution”, Tetrahedron Letters, vol. 55, pp. 2517 – 2522.
  • Rajasekaran, D., Venkatachalam, K., Periasamy, V., 2020, “A bisphenol based fluorescence chemosensor for the selective detection of Zn2+ and PPi ions and its bioluminescence imaging”, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, vol. 242, pp 118730.
  • Roy, N., Dutta, A., Mondal, P., Paul, P. C., Singh, T. S., 2016, “A new coumarin based dual functional chemosensor for colorimetric detection of Fe3+ and fluorescence turn-on responde of Zn2+”, Sensors and Actuators B: Chemical, vol 236, pp 719 – 731.
  • Sasaki, H., Hanaoka, K., Urano, Y., Terai, T., Nagano, T., 2011, “Design and synthesis of a novel fluorescence probe for Zn2+ based on the spirolactam ring-opening process of rhodamine derivatives”, Bioorganic & Medicinal Chemistry, vol.19, pp 1072 – 1078.
  • Shao, Y. ve diğ., 2015, “Advances in molecular quantum chemistry contained in the Q-Chem 4 program package”, Molecular Physics, vol. 113, pp. 184-215.
  • Tabakci B., Ahmed, H. M. A., Erdemir, S., 2019, “Fast and Reversible “Turn on” Fluorescent Sensors Based on Bisphenol-a for Zn2+ in Aqueous Solution”, Journal of Fluorescence, vol. 29, pp. 1049 – 1087.
  • Venkatesan, V., R. Kumar, S., Kumar, S. K. A., Sahoo, S. K., 2019, “Highly selective turn-on fluorogenic chemosensor for Zn2+ based on chelation enhanced fluorescence”, Inorganic Chemistry Communications, vol. 102, pp. 171 – 179.
  • Wang, R., Wang, N., Tu, Y., Liu, G., Pu, S., 2018, “A new fluorescence based on diarylethene with a N’-(quinolin-8-ylmethylene)benzohydrazide group for Zn2+ detection”, Journal of Photochemistry & Photobiology A: Chemistry, vol. 364, pp. 32 – 39.
  • Xu, T., Duan, H., Wang, X., Meng, X., Bu, J., 2015, “Fluorescence sensors for Zn2+ based on conjugated indole Schiff base”, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, vol. 138, pp 603 – 608.
  • Zhu, J., Zhang, Y., Chen, Y., Sun, T., Tang, Y., Huang, Y., Yang, Q., Ma, D., Wang, Y., Wang, M., 2017, “A Schiff base fluorescence probe for highly selective turn-on recognition of Zn2+”, Tetrahedron Letters, vol. 58, pp. 365 – 370.
There are 26 citations in total.

Details

Primary Language Turkish
Subjects Engineering
Journal Section Research Article
Authors

Yasemin Ünsal 0000-0002-5835-2426

Egemen Özçelik 0000-0002-2604-4656

Mustafa Tabakcı 0000-0003-2941-2191

Publication Date December 30, 2021
Submission Date August 15, 2021
Acceptance Date December 21, 2021
Published in Issue Year 2021 Volume: 9

Cite

IEEE Y. Ünsal, E. Özçelik, and M. Tabakcı, “FENOLFTALEİN TABANLI FLORESANS SENSÖR SENTEZİ VE SULU ORTAMDA AĞIR METALLERE KARŞI OPTİK ÖZELLİKLERİNİN İNCELENMESİ”, KONJES, vol. 9, pp. 187–199, 2021, doi: 10.36306/konjes.983194.