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Synthesis, Characterization and Metal Ion Extraction Study of New Phthalocyanine Derivative Containing Piperazinedion Moiety

Year 2024, , 1071 - 1080, 01.10.2024

Halil Zeki Gök

https://doi.org/10.35414/akufemubid.1456335

Abstract

In this study, starting from the phthalonitrile compound 1 recorded in the literature, a new macrocyclic compound 2 containing a piperazinedione unit and its cobalt(II) phthalocyanine derivative 3 were synthesized. The compounds 2 and 3 was characterized by using the analyses such as FT-IR, 1H and 13 C NMR, MS and UV-Vis. Liquid-liquid extraction experiments were performed to understand the extractant properties of the precursor phthalonitrile compound 1, macrocyclic compound 2 and 3. For this, the liquid-liquid extraction method was used. It was attempted to determine at what rate 1, 2 and 3 transport Ag+, Hg2+, Cd2+, Zn2+, Cu2+, Ni2+, Pb2+, and Co2+ metal ions from the aqueous phase to the organic phase. In addition, the effect of macrocyclic ring size and the number of donor atoms in the macrocyclic ring on metal-ion extraction is given by comparing the results obtained from previous studies. Extraction studies using the compounds 1, 2 and 3 have shown that the compound 3 transports Hg2+ ve Cu2+ cations at the highest rate. The extraction percentages of Hg2+ ve Cu2+ cations from the aqueous phase to the chloroform phase in the presence of compound 3 were determined as 89.9% and 83.1%, respectively.

Keywords

Macrocycle Phthalocyanine Metal extraction

Project Number

OKÜ BAPK-2015-PT2-009

References

  • Akkuş, G. U. and Öz, E. K., 2014. Halkalı Yapıdaki Kaliks-crown Türevlerinin Sentezi ve Faz-transfer Reaksiyonlarında Kullanılması. Afyon Kocatepe Üniversitesi Fen Ve Mühendislik Bilimleri Dergisi, 14(1), 1-6. https://doi.org/10.5578/fmbd.6913
  • Armarego, W. L., 2022. Purification of laboratory chemicals: Part 2 inorganic chemicals, catalysts, biochemicals, physiologically active chemicals, nanomaterials. Butterworth-Heinemann. Das, S., Chatterjee, S., Mondal, S., Modak, A., Chandra, B. K., Das, S. and Bhaumik, A., 2020. Thiadiazole containing N-and S-rich highly ordered periodic mesoporous organosilica for efficient removal of Hg (II) from polluted water. Chemical communications, 56(28), 3963-3966. https://doi.org/10.1039/D0CC00407C
  • Furukawa, M. and Tokunaga, S., 2004. Extraction of heavy metals from a contaminated soil using citrate-enhancing extraction by pH control and ultrasound application. Journal of Environmental Science and Health, Part A, 39(3), 627-638. https://doi.org/10.1081/ESE-120027729
  • Gök, H. Z. and Gök, Y., 2019. Novel polymeric phthalocyanines bridged flexible 1, 5-pentanedithiol unit for metal ions extraction: synthesis, characterization and evaluation. Journal of Inclusion Phenomena and Macrocyclic Chemistry, 94, 55-63. https://doi.org/10.1007/s10847-019-00901-1
  • Gök, H. Z. and Gök Y., 2018. A novel n-pivot macrocyclic ligand and its Cobalt (II) phthalocyanine derivative: synthesis, characterization and extractant properties. Scientific Journal of Mehmet Akif Ersoy University, 1(2), 40-45.
  • Gök, H. Z. and Gök Y., 2018. The solution and extractant properties of metal-free and metallophthalocyanines substituted by four macrocycles containing piperazinedion moiety. International Eurasian Conference on Biological and Chemical Sciences (EurasianBioChem 2018). Ankara, Turkey, 289-296.
  • Gök, H. Z. and Gök, Y., 2017. Synthesis, characterization, and metal‐ion binding properties of a new macrobicyclic ligand with dioxadiazaoctathia donor atoms. Heteroatom Chemistry, 28(3), e21374. https://doi.org/10.1002/hc.21374
  • Gök, H. Z., 2015. Synthesis of metal-free and metallophthalocyanines containing 18-and 21-membered macrocycles with mixed donor atoms and their metal-ion binding properties. Turkish Journal of Chemistry, 39(4), 750-763. https://doi.org/10.3906/kim-1501-54
  • Gök, H. Z. and Demir, H., 2015. Complexation and adsorption studies of 27-membered dioxadiazapentathia macrocycles with some transition metals. Separation Science and Technology, 50(11), 1593-1601. https://doi.org/10.1080/01496395.2014.983247
  • Gök, H. Z., Gök, Y. and Eker, E., 2015. Synthesis, characterization, and metal extraction studies of a new macrobicyclic ligand. Turkish Journal of Chemistry, 39(2), 426-437. https://doi.org/10.3906/kim-1412-27
  • Gök, H. Z. and Gök, Y., 2014. Synthesis and characterization of new organosoluble metal-free and metallophthalocyanines substituted by four macrocycles containing piperazine moiety. Inorganic Chemistry Communications, 40, 164-167. https://doi.org/10.1016/j.inoche.2013.12.008
  • Gök, H. Z., Kantekin, H., Gök, Y. and Herman, G., 2007. The synthesis and characterization of new metal-free and metallophthalocyanines containing four 27-membered diazaheptathia macrocycles. Dyes and Pigments, 75(3), 606-611. https://doi.org/10.1016/j.dyepig.2006.07.008
  • Gök, H. Z., Kantekin, H., Gök, Y. and Herman, G., 2007. The synthesis and characterization of novel metal-free and metallophthalocyanines bearing four 27-membered dioxadiazapentathia macrocycles. Dyes and Pigments, 74(3), 699-705. https://doi.org /10.1016/j.dyepig.2006.05.002
  • Hancock, R. D. and Martell, A. E., 1989. Ligand design for selective complexation of metal ions in aqueous solution. Chemical Reviews, 89(8), 1875-1914. https://doi.org/10.1021/cr00098a011
  • Izatt, R. M., Bradshaw, J. S., Nielsen, S. A., Lamb, J. D., Christensen, J. J. and Sen, D., 1985. Thermodynamic and kinetic data for cation-macrocycle interaction. Chemical Reviews, 85(4), 271-339. https://doi.org/10.1021/cr00068a003
  • Kabay, N. and Gök, Y., 2013. Synthesis and characterization of metal-free phthalocyanine containing 16-membered N2S2-donor macrocycles linked to a 2-pyridinyl methyl moiety. Tetrahedron Letters, 54(31), 4086-4090. https://doi.org/10.1016/j.tetlet.2013.05.125
  • Leznoff, C.C. and Lever, A.B.P., 1998. Phthalocyanines: Properties and Applications, vol. 1–4. VCH, Weinheim. Malato, S., Fernández-Ibáñez, P., Maldonado, M. I., Blanco, J. and Gernjak, W., 2009. Decontamination and disinfection of water by solar photocatalysis: recent overview and trends. Catalysis Today, 147(1), 1-59. https://doi.org/10.1016/j.cattod.2009.06.018
  • Pedersen, C. J., 1967. Cyclic polyethers and their complexes with metal salts. Journal of the American Chemical Society, 89(26), 7017-7036. https://doi.org/10.1021/ja01002a035
  • Rehman, K., Fatima, F., Waheed, I. and Akash, M. S. H., 2018. Prevalence of exposure of heavy metals and their impact on health consequences. Journal of Cellular Biochemistry, 119(1), 157-184. https://doi.org/10.1002/jcb.26234
  • Rout, A. and Binnemans, K., 2014. Separation of rare earths from transition metals by liquid–liquid extraction from a molten salt hydrate to an ionic liquid phase. Dalton Transactions, 43(8), 3186-3195. https://doi.org/10.1039/C3DT52541D
  • Shuya, L., Yang, C., Xuefeng, C., Wei, S., Yaqing, W. and Yue, Y., 2020. Separation of lithium and transition metals from leachate of spent lithium-ion batteries by solvent extraction method with Versatic 10. Separation and Purification Technology, 250, 117258. https://doi.org/10.1016/j.seppur.2020.117258
  • Yıldız, Y. B., 2024. Synthesis and characterization of zinc (II) phthalocyanine containing 17-membered macrocyclic moiety as new extractant for the removal of Ag (I) from aqueous solution. Transition Metal Chemistry, 1-8. https://doi.org/10.1007/s11243-024-00577-8
  • Yordanov, A.T. and Roundhill, D.M., 1998. Solution extraction of transition and post-transition heavy and precious metals by chelate and macrocyclic macrocyclic ligands. Coordination Chemistry Reviews, 170, 93-124. https://doi.org/10.1016/S0010-8545(97)00074-X
  • Zhang, X. X., Izatt, R. M., Bradshaw, J. S. and Krakowiak, K. E., 1998. Approaches to improvement of metal ion selectivity by cryptands. Coordination Chemistry Reviews, 174(1), 179-189. https://doi.org/10.1016/S0010-8545(98)00050-2

Piperazindion Birimi İçeren Yeni Bir Ftalosiyanin Bileşiğinin Sentezi, Karakterizasyonu ve Metal Ekstraksiyon Özelliklerinin İncelenmesi

Year 2024, , 1071 - 1080, 01.10.2024

Halil Zeki Gök

https://doi.org/10.35414/akufemubid.1456335

Abstract

Bu çalışmada, literatürde yer alan ftalonitril 1 bileşiğinden başlanarak piperazinedion birimi içeren yeni bir makrosiklik bileşik 2 ve bu makrosiklik bileşiğin kobalt(II) ftalosiyanin türevi 3 sentezlenmiştir. Sentezi gerçekleştirilen bileşik 2 ve 3’ün karakterizasyonları FT-IR, MS, UV-Vis, 1H ve 13C NMR analiz yöntemleri kullanılarak gerçekleştirilmiştir. Öncül ftalonitril bileşiği 1, makrosiklik bileşik 2 ve kobalt(II) ftalosiyanin türevi 3’ün ekstraktant özelliklerini belirlemek amacıyla sıvı-sıvı ekstraksiyon deneyleri gerçekleştirilmiştir. Bunun için, sıvı-sıvı ekstraksiyonu yöntemi kullanılmıştır. 1, 2 ve 3 bileşiklerinin, sulu fazdan Ag+, Hg2+, Cd2+, Zn2+, Cu2+, Ni2+, Pb2+ ve Co2+ metal iyonlarını organik faza hangi oranda taşıdığı belirlenmeye çalışılmıştır. Bunun yanı sıra, makrosiklik halka büyüklüğü ve makrosiklik halkadaki donör atom sayısının metal-iyon ekstraksiyonu üzerine olan etkisi, daha önce yapılan çalışmalardan elde edilen sonuçlar ile karşılaştırılarak verilmiştir. 1, 2 ve 3 bileşiklerinin kullanılması ile yapılan ekstraksiyon çalışmaları, 3 bileşiğinin Hg2+ ve Cu2+ katyonlarını sulu fazdan organik faza en yüksek oranda taşıdığını göstermiştir. Kobalt(II) ftalosiyanin 3 bileşiği ile Hg2+ ve Cu2+ katyonlarının sulu fazdan kloroform fazına ekstraksiyon yüzdeleri sırasıyla %89,9 ve %83,1 olarak belirlenmiştir.

Keywords

Makrosiklik Ftalosiyanin Metal ekstraksiyonu Geçiş Metallerı

Ethical Statement

Yazarlar tüm etik standartlara uyduklarını beyan ederler.

Supporting Institution

Osmaniye Korkut Ata Üniversitesi Bilimsel Araştırma Projeleri Koordinatörlüğü

Project Number

OKÜ BAPK-2015-PT2-009

Thanks

Bu araştırmanın bir kısmı Osmaniye Korkut Ata Üniversitesi Bilimsel Araştırma Projeleri Koordinatörlüğü tarafından desteklenmiştir (Proje No: OKÜ BAPK-2015-PT2-009). UV-Vis ölçümleri için imkân sağlayan Doç. Dr. Soner Dönmez’e ve ölçümlerin alınması sırasında yardımcı olan doktorant Osman Tayyar Arlı’ya teşekkür ederiz

References

  • Akkuş, G. U. and Öz, E. K., 2014. Halkalı Yapıdaki Kaliks-crown Türevlerinin Sentezi ve Faz-transfer Reaksiyonlarında Kullanılması. Afyon Kocatepe Üniversitesi Fen Ve Mühendislik Bilimleri Dergisi, 14(1), 1-6. https://doi.org/10.5578/fmbd.6913
  • Armarego, W. L., 2022. Purification of laboratory chemicals: Part 2 inorganic chemicals, catalysts, biochemicals, physiologically active chemicals, nanomaterials. Butterworth-Heinemann. Das, S., Chatterjee, S., Mondal, S., Modak, A., Chandra, B. K., Das, S. and Bhaumik, A., 2020. Thiadiazole containing N-and S-rich highly ordered periodic mesoporous organosilica for efficient removal of Hg (II) from polluted water. Chemical communications, 56(28), 3963-3966. https://doi.org/10.1039/D0CC00407C
  • Furukawa, M. and Tokunaga, S., 2004. Extraction of heavy metals from a contaminated soil using citrate-enhancing extraction by pH control and ultrasound application. Journal of Environmental Science and Health, Part A, 39(3), 627-638. https://doi.org/10.1081/ESE-120027729
  • Gök, H. Z. and Gök, Y., 2019. Novel polymeric phthalocyanines bridged flexible 1, 5-pentanedithiol unit for metal ions extraction: synthesis, characterization and evaluation. Journal of Inclusion Phenomena and Macrocyclic Chemistry, 94, 55-63. https://doi.org/10.1007/s10847-019-00901-1
  • Gök, H. Z. and Gök Y., 2018. A novel n-pivot macrocyclic ligand and its Cobalt (II) phthalocyanine derivative: synthesis, characterization and extractant properties. Scientific Journal of Mehmet Akif Ersoy University, 1(2), 40-45.
  • Gök, H. Z. and Gök Y., 2018. The solution and extractant properties of metal-free and metallophthalocyanines substituted by four macrocycles containing piperazinedion moiety. International Eurasian Conference on Biological and Chemical Sciences (EurasianBioChem 2018). Ankara, Turkey, 289-296.
  • Gök, H. Z. and Gök, Y., 2017. Synthesis, characterization, and metal‐ion binding properties of a new macrobicyclic ligand with dioxadiazaoctathia donor atoms. Heteroatom Chemistry, 28(3), e21374. https://doi.org/10.1002/hc.21374
  • Gök, H. Z., 2015. Synthesis of metal-free and metallophthalocyanines containing 18-and 21-membered macrocycles with mixed donor atoms and their metal-ion binding properties. Turkish Journal of Chemistry, 39(4), 750-763. https://doi.org/10.3906/kim-1501-54
  • Gök, H. Z. and Demir, H., 2015. Complexation and adsorption studies of 27-membered dioxadiazapentathia macrocycles with some transition metals. Separation Science and Technology, 50(11), 1593-1601. https://doi.org/10.1080/01496395.2014.983247
  • Gök, H. Z., Gök, Y. and Eker, E., 2015. Synthesis, characterization, and metal extraction studies of a new macrobicyclic ligand. Turkish Journal of Chemistry, 39(2), 426-437. https://doi.org/10.3906/kim-1412-27
  • Gök, H. Z. and Gök, Y., 2014. Synthesis and characterization of new organosoluble metal-free and metallophthalocyanines substituted by four macrocycles containing piperazine moiety. Inorganic Chemistry Communications, 40, 164-167. https://doi.org/10.1016/j.inoche.2013.12.008
  • Gök, H. Z., Kantekin, H., Gök, Y. and Herman, G., 2007. The synthesis and characterization of new metal-free and metallophthalocyanines containing four 27-membered diazaheptathia macrocycles. Dyes and Pigments, 75(3), 606-611. https://doi.org/10.1016/j.dyepig.2006.07.008
  • Gök, H. Z., Kantekin, H., Gök, Y. and Herman, G., 2007. The synthesis and characterization of novel metal-free and metallophthalocyanines bearing four 27-membered dioxadiazapentathia macrocycles. Dyes and Pigments, 74(3), 699-705. https://doi.org /10.1016/j.dyepig.2006.05.002
  • Hancock, R. D. and Martell, A. E., 1989. Ligand design for selective complexation of metal ions in aqueous solution. Chemical Reviews, 89(8), 1875-1914. https://doi.org/10.1021/cr00098a011
  • Izatt, R. M., Bradshaw, J. S., Nielsen, S. A., Lamb, J. D., Christensen, J. J. and Sen, D., 1985. Thermodynamic and kinetic data for cation-macrocycle interaction. Chemical Reviews, 85(4), 271-339. https://doi.org/10.1021/cr00068a003
  • Kabay, N. and Gök, Y., 2013. Synthesis and characterization of metal-free phthalocyanine containing 16-membered N2S2-donor macrocycles linked to a 2-pyridinyl methyl moiety. Tetrahedron Letters, 54(31), 4086-4090. https://doi.org/10.1016/j.tetlet.2013.05.125
  • Leznoff, C.C. and Lever, A.B.P., 1998. Phthalocyanines: Properties and Applications, vol. 1–4. VCH, Weinheim. Malato, S., Fernández-Ibáñez, P., Maldonado, M. I., Blanco, J. and Gernjak, W., 2009. Decontamination and disinfection of water by solar photocatalysis: recent overview and trends. Catalysis Today, 147(1), 1-59. https://doi.org/10.1016/j.cattod.2009.06.018
  • Pedersen, C. J., 1967. Cyclic polyethers and their complexes with metal salts. Journal of the American Chemical Society, 89(26), 7017-7036. https://doi.org/10.1021/ja01002a035
  • Rehman, K., Fatima, F., Waheed, I. and Akash, M. S. H., 2018. Prevalence of exposure of heavy metals and their impact on health consequences. Journal of Cellular Biochemistry, 119(1), 157-184. https://doi.org/10.1002/jcb.26234
  • Rout, A. and Binnemans, K., 2014. Separation of rare earths from transition metals by liquid–liquid extraction from a molten salt hydrate to an ionic liquid phase. Dalton Transactions, 43(8), 3186-3195. https://doi.org/10.1039/C3DT52541D
  • Shuya, L., Yang, C., Xuefeng, C., Wei, S., Yaqing, W. and Yue, Y., 2020. Separation of lithium and transition metals from leachate of spent lithium-ion batteries by solvent extraction method with Versatic 10. Separation and Purification Technology, 250, 117258. https://doi.org/10.1016/j.seppur.2020.117258
  • Yıldız, Y. B., 2024. Synthesis and characterization of zinc (II) phthalocyanine containing 17-membered macrocyclic moiety as new extractant for the removal of Ag (I) from aqueous solution. Transition Metal Chemistry, 1-8. https://doi.org/10.1007/s11243-024-00577-8
  • Yordanov, A.T. and Roundhill, D.M., 1998. Solution extraction of transition and post-transition heavy and precious metals by chelate and macrocyclic macrocyclic ligands. Coordination Chemistry Reviews, 170, 93-124. https://doi.org/10.1016/S0010-8545(97)00074-X
  • Zhang, X. X., Izatt, R. M., Bradshaw, J. S. and Krakowiak, K. E., 1998. Approaches to improvement of metal ion selectivity by cryptands. Coordination Chemistry Reviews, 174(1), 179-189. https://doi.org/10.1016/S0010-8545(98)00050-2
There are 24 citations in total.

Details

Primary Language Turkish
Subjects Inorganic Chemistry (Other)
Journal Section Articles
Authors

Halil Zeki Gök 0000-0001-7641-2683

Project Number OKÜ BAPK-2015-PT2-009
Early Pub Date September 10, 2024
Publication Date October 1, 2024
Submission Date March 21, 2024
Acceptance Date June 29, 2024
Published in Issue Year 2024

Cite

APA Gök, H. Z. (2024). Piperazindion Birimi İçeren Yeni Bir Ftalosiyanin Bileşiğinin Sentezi, Karakterizasyonu ve Metal Ekstraksiyon Özelliklerinin İncelenmesi. Afyon Kocatepe Üniversitesi Fen Ve Mühendislik Bilimleri Dergisi, 24(5), 1071-1080. https://doi.org/10.35414/akufemubid.1456335
AMA Gök HZ. Piperazindion Birimi İçeren Yeni Bir Ftalosiyanin Bileşiğinin Sentezi, Karakterizasyonu ve Metal Ekstraksiyon Özelliklerinin İncelenmesi. Afyon Kocatepe Üniversitesi Fen Ve Mühendislik Bilimleri Dergisi. October 2024;24(5):1071-1080. doi:10.35414/akufemubid.1456335
Chicago Gök, Halil Zeki. “Piperazindion Birimi İçeren Yeni Bir Ftalosiyanin Bileşiğinin Sentezi, Karakterizasyonu Ve Metal Ekstraksiyon Özelliklerinin İncelenmesi”. Afyon Kocatepe Üniversitesi Fen Ve Mühendislik Bilimleri Dergisi 24, no. 5 (October 2024): 1071-80. https://doi.org/10.35414/akufemubid.1456335.
EndNote Gök HZ (October 1, 2024) Piperazindion Birimi İçeren Yeni Bir Ftalosiyanin Bileşiğinin Sentezi, Karakterizasyonu ve Metal Ekstraksiyon Özelliklerinin İncelenmesi. Afyon Kocatepe Üniversitesi Fen Ve Mühendislik Bilimleri Dergisi 24 5 1071–1080.
IEEE H. Z. Gök, “Piperazindion Birimi İçeren Yeni Bir Ftalosiyanin Bileşiğinin Sentezi, Karakterizasyonu ve Metal Ekstraksiyon Özelliklerinin İncelenmesi”, Afyon Kocatepe Üniversitesi Fen Ve Mühendislik Bilimleri Dergisi, vol. 24, no. 5, pp. 1071–1080, 2024, doi: 10.35414/akufemubid.1456335.
ISNAD Gök, Halil Zeki. “Piperazindion Birimi İçeren Yeni Bir Ftalosiyanin Bileşiğinin Sentezi, Karakterizasyonu Ve Metal Ekstraksiyon Özelliklerinin İncelenmesi”. Afyon Kocatepe Üniversitesi Fen Ve Mühendislik Bilimleri Dergisi 24/5 (October 2024), 1071-1080. https://doi.org/10.35414/akufemubid.1456335.
JAMA Gök HZ. Piperazindion Birimi İçeren Yeni Bir Ftalosiyanin Bileşiğinin Sentezi, Karakterizasyonu ve Metal Ekstraksiyon Özelliklerinin İncelenmesi. Afyon Kocatepe Üniversitesi Fen Ve Mühendislik Bilimleri Dergisi. 2024;24:1071–1080.
MLA Gök, Halil Zeki. “Piperazindion Birimi İçeren Yeni Bir Ftalosiyanin Bileşiğinin Sentezi, Karakterizasyonu Ve Metal Ekstraksiyon Özelliklerinin İncelenmesi”. Afyon Kocatepe Üniversitesi Fen Ve Mühendislik Bilimleri Dergisi, vol. 24, no. 5, 2024, pp. 1071-80, doi:10.35414/akufemubid.1456335.
Vancouver Gök HZ. Piperazindion Birimi İçeren Yeni Bir Ftalosiyanin Bileşiğinin Sentezi, Karakterizasyonu ve Metal Ekstraksiyon Özelliklerinin İncelenmesi. Afyon Kocatepe Üniversitesi Fen Ve Mühendislik Bilimleri Dergisi. 2024;24(5):1071-80.


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