Research Article
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Year 2019, Volume 1, Issue 1, 11.12.2019

Abstract

References

  • [1] Spietelun, A., Marcinkowski, L., Guardia, M., Namieśnik, J. 2014. ‘’Green aspects, developments and perspectives of liquid phase microextraction techniques’’ Talanta 119 34–45. [2] Rezaee, M., Assadi, Y., Milani Hosseini, M.R., Aghaee, E., Ahmadi, F., Berijani, S. 2006. ‘’Determination of organic compounds in water using dispersive liquid-liquid microextraction’’ J. Chromatogr. A 1116 1–9. [3] Herrera-Herrera, A.V., Asensio-Ramos, M., Hernàndez-Borges, J., RodriguezDelgado, M.A. 2010. ‘’Dispersive liquid-liquid microextraction for determination of organic analytes’’ Trends Anal. Chem. 29 (7) 728–751.[4] Kadish, K.M., Smith, K.M., Guilard, R. 2010. Handbook of porphyrin science. Singapore: World Scientific Publishing. [5] Donzello, M.P., Ercolani, C., Novakova, V., Zimcik, P., Stuzhin, P.A. 2016. ‘’Tetrapyrazinoporphyrazines and their metal derivatives. Part I: Synthesis and basic structural information’’ Coord. Chem. Rev. 309 107-179. [6] M.P. Donzello, D. Vittori, E. Viola, L.H. Zeng, Y. Cui, K.M. Kadish, 2015. ‘’Tetra-2,3-pyrazinoporphyrazines with externally appended pyridine rings 14: UV-visible spectral and electrochemical behavior of homo/heterobinuclear neutral and hexacationic macrocycles’’ J. Porphyr. Phthalocyanines 17 896-904. [7] M. Kucinska, P. Skupin-Mrugalska, W. Szczolko, L. Sobotta, M. Sciepura, E. Tykarska, 2015. ‘’Phthalocyanine derivatives possessing 2-(morpholin-4-yl)ethoxy groups as potential agents for photodynamic therapy’’ J. Med. Chem 58 2240-2255. [8] J.T.F. ƒLau, P-C. Lo, X-J. Jiang, Q. Wang, D.K.P. Ng, 2014. ‘’Synthesis and Photodynamic Effect of New Highly Photostable Decacationically Armed [60]- and [70]Fullerene Decaiodide Monoadducts To Target Pathogenic Bacteria and Cancer Cells’’ J. Med. Chem. 57 4088-4097. [9] M.P. Donzello, E. Viola, C. Ercolani, Z. Fu, D. Futur, K.M. Kadish, 2012. ‘’Tetra-2,3-pyrazinoporphyrazines with externally appended pyridine rings. 12. New heteropentanuclear complexes carrying four exocyclic cis-platin-like functionalities as potential bimodal (PDT/cis-platin) anticancer agents’’ Inorg. Chem. 51 12548-12559.[10] A. Hagfeldt, G. Boschloo, L.C. Sun, L. Kloo, H. Pettersson, 2010. ‘’Dye-sensitized solar cells’’ Chem. Rev. 110 6595-65663. [11] M-E Ragoussi, M. Ince, T. Torres, 2013. ‘’Recent Advances in Phthalocyanine Based Sensitizers for Dye Sensitized Solar Cells’’ Eur. J. Org. Chem. 29 6475-6489. [12] L. Lochman, J. Svec, J. Roh, K. Kirakci, K. Lang, P. Zimcik, 2016. ‘’Azaphthalocyanines: Red Fluorescent Probes for Cations’’ Chem. Eur. J. 22, 2417-2426. [13] V. Novakova, M. Laskova, H. Vavrickova, P. Zimcik, 2015. ‘’Phenol Substituted Tetrapyrazinoporphyrazines: pH Dependent Fluorescence in Basic Media’’ Chem. Eur. J. 21 14382-14392. [14] I.V. Nesterova, C.A. Bennett, S.S. Erdem, R.P. Hammer, P.L. Deininger, S.A. Soper, 2011. ‘’Near-IR single fluorophore quenching system based on phthalocyanine (Pc) aggregation and its application for monitoring inhibitor/activator action on a therapeutic target: L1-EN’’ Analyst 136 1103-1105. [15] P. Zimcik, V. Novakova, K. Kopecky, M. Miletin, R.Z. Uslu Kobak, E. Svandrlikova, 2012. ‘’Magnesium azaphthalocyanines: an emerging family of excellent red-emitting fluorophores’’ Inorg. Chem. 51 4215-4223. [16] D. Wohrle, G. Schnurpfeil, S.G. Makarov, A. Kazarin, O.N. Suvorova, 2012. ‘’ Practical Applications of Phthalocyanines – from Dyes and Pigments to Materials for Optical, Electronic and Photo-electronic Devices’’ Macroheterocycles 5 191-202.[17] P. Zimcik, A. Malkova, L. Hruba, M. Miletin, V. Novakova, 2017. ‘’Bulky 2,6-diphenylphenylsulfanyl substituents efficiently inhibit aggregation in phthalocyanines and tetrapyrazinoporphyrazines and control their photophysical and electrochemical properties’’ Dyes and Pigments 136 715-723.[18] T.W. Lin, S.D. Huang, 2001. ‘’Direct and simultaneous determination of copper, chromium, aluminum and manganese in urine with a multielement graphite furnace atomic absorption spectrometer’’ Anal. Chem. 73 (17) 4319-4325.[19] C.N. Sawyer, P.L. McCarty, G.F. Parkin, Chemistry for Environmental Engineering, fourth ed., McGraw-Hill, New York, 1996, p. 634. [20] L. Feng, Y. Zhang, L. Wen, Z. Shen, Y. Guan, 2011. ‘’Colorimetric determination of copper (II) ions by filtration on sol-gel membrane doped with diphenylcarbazide’’ Talanta 84 (3) 913-917. [21] C. Pfeiffer, R. Mailloux, 1987. ‘’Excess copper as a factor in human diseases’’ J. Orthomol. Med. 2 (3) 171-182. [22] Yamini, Y., Hassan, J., Karbasi, M.H. 2004. ‘’Solid phase extraction of copper and cupron on octadecyl silica cartridge and its determination with atomic absorption spectrometry’’ Microchim. Acta 148 (3-4) 305-309. [23] Alkan, D., Kara, M. 2002. ‘’Preconcentration and separation of copper(II) with solvent extraction using N,N0 -bis(2-hydroxy-5- bromo-benzyl) 1,2 diaminopropane, Microchem. J. 71 29-39. [24] Tobiasz, A., Walas, S., Soto Hernandes, A., Mrowiec, H. 2012. ‘’Application of multiwall carbon nanotubes impregnated with 5- dodecylsalicylaldoxime for on-line copper preconcentration and determination in water samples by flame atomic absorption spectrometry’’ Talanta 96 89-95. [25] Gao, Y., Wu, P., Li, W., Xuan, Y., Hou, X. 2010. ‘’Simultaneous and selective preconcentration of trace Cu and Ag by one-step displacement cloud point extraction for FAAS determination’’ Talanta 81 586-590. [26] Alver, E., Demirci, A., Ozcimder, M. 2012. ‘’Microextraction methods’’ Sigma J. Eng. Nat. Sci. 30 75-90. [27] Kandhro, G., Soylak, M., Kazı, T.G., Yılmaz, E. 2014. ‘’Enrichment of copper as 1-(2-pyridylazo)-2-naphthol complex by the combination of dispersive liquid-liquid micro-extraction/flame atomic absorption spectrometry’’ J. AOAC Int. 97 205-210. [28] Stanisz, E., Zgola-Grzeskowiak, A. 2013. ‘’In situ metathesis ionic liquid formation dispersive liquid-liquid microextraction for copper in water samples by electrothermal atomic absorption spectrometry’’ Talanta 115 178-183. [29] Baghdadi, M., Shemirani, F. 2008 ‘’Cold-induced aggregation microextraction: a novel sample preparation technique based on ionic liquids’’ Anal. Chim. Acta 613 56-63.[30] Çağlar, Y., Saka, E.T., Alp, H., Kantekin, H., Ocak, Ü., Ocak, M. 2016. ‘’A Simple Spectrofluorimetric Method Based on Quenching of a Nickel(II)-Phthalocyanine Complex to Determine Iron (III)’’ Journal of Fluorescence 26 1381-1389.

A novel silicone phthalocyanine for the preconcentration and spectrophotometric determination of copper by ionic liquid-based dispersive liquid-liquid microextraction

Year 2019, Volume 1, Issue 1, 11.12.2019

Abstract

Dispersive liquid-liquid microextraction (DLLME) has become a very popular environmentally benign sample preparation technique, due to its simplicity, speed of operation and low consumption of solvent and reagent. It has attracted much interest from scientists working in separation science, and much improvement has been made since its introduction in 2006. This work reports the development of a new simple ionic liquid based dispersive liquid-liquid microextraction (IL-DLLME) method for spectrophotometric copper determination. First, the copper was complexed with a novel silicone phthalocyanine and than the complex was extracted into 1-heptyl-3-methylimidazolium hexafluorophosphate dissolving in acetone in the presence of sodium dodecyl sulphate (SDS) as the anti-sticking agent. After centrifuging for 2 min at 3000 rpm, the extracting phase was diluted to 250 µL with acetone for spectrophtometric detection at 340 nm. Some experimental conditions that influence the procedure were optimized. The pH and complexing reagent concentration are 4.0 and 4.6x10-6 molL-1, respectively. The method is linear in the range from 0.03 to 100 µg/mL with a correlation coefficient (R2) of 0.9973. The limit of detection (LOD) of method is 0.017 µg/mL. The relative standard deviation is 1.7% at 45 µg/mL Cu2+ (n=6).  The enrichment factor for the method was calculated as 210.

References

  • [1] Spietelun, A., Marcinkowski, L., Guardia, M., Namieśnik, J. 2014. ‘’Green aspects, developments and perspectives of liquid phase microextraction techniques’’ Talanta 119 34–45. [2] Rezaee, M., Assadi, Y., Milani Hosseini, M.R., Aghaee, E., Ahmadi, F., Berijani, S. 2006. ‘’Determination of organic compounds in water using dispersive liquid-liquid microextraction’’ J. Chromatogr. A 1116 1–9. [3] Herrera-Herrera, A.V., Asensio-Ramos, M., Hernàndez-Borges, J., RodriguezDelgado, M.A. 2010. ‘’Dispersive liquid-liquid microextraction for determination of organic analytes’’ Trends Anal. Chem. 29 (7) 728–751.[4] Kadish, K.M., Smith, K.M., Guilard, R. 2010. Handbook of porphyrin science. Singapore: World Scientific Publishing. [5] Donzello, M.P., Ercolani, C., Novakova, V., Zimcik, P., Stuzhin, P.A. 2016. ‘’Tetrapyrazinoporphyrazines and their metal derivatives. Part I: Synthesis and basic structural information’’ Coord. Chem. Rev. 309 107-179. [6] M.P. Donzello, D. Vittori, E. Viola, L.H. Zeng, Y. Cui, K.M. Kadish, 2015. ‘’Tetra-2,3-pyrazinoporphyrazines with externally appended pyridine rings 14: UV-visible spectral and electrochemical behavior of homo/heterobinuclear neutral and hexacationic macrocycles’’ J. Porphyr. Phthalocyanines 17 896-904. [7] M. Kucinska, P. Skupin-Mrugalska, W. Szczolko, L. Sobotta, M. Sciepura, E. Tykarska, 2015. ‘’Phthalocyanine derivatives possessing 2-(morpholin-4-yl)ethoxy groups as potential agents for photodynamic therapy’’ J. Med. Chem 58 2240-2255. [8] J.T.F. ƒLau, P-C. Lo, X-J. Jiang, Q. Wang, D.K.P. Ng, 2014. ‘’Synthesis and Photodynamic Effect of New Highly Photostable Decacationically Armed [60]- and [70]Fullerene Decaiodide Monoadducts To Target Pathogenic Bacteria and Cancer Cells’’ J. Med. Chem. 57 4088-4097. [9] M.P. Donzello, E. Viola, C. Ercolani, Z. Fu, D. Futur, K.M. Kadish, 2012. ‘’Tetra-2,3-pyrazinoporphyrazines with externally appended pyridine rings. 12. New heteropentanuclear complexes carrying four exocyclic cis-platin-like functionalities as potential bimodal (PDT/cis-platin) anticancer agents’’ Inorg. Chem. 51 12548-12559.[10] A. Hagfeldt, G. Boschloo, L.C. Sun, L. Kloo, H. Pettersson, 2010. ‘’Dye-sensitized solar cells’’ Chem. Rev. 110 6595-65663. [11] M-E Ragoussi, M. Ince, T. Torres, 2013. ‘’Recent Advances in Phthalocyanine Based Sensitizers for Dye Sensitized Solar Cells’’ Eur. J. Org. Chem. 29 6475-6489. [12] L. Lochman, J. Svec, J. Roh, K. Kirakci, K. Lang, P. Zimcik, 2016. ‘’Azaphthalocyanines: Red Fluorescent Probes for Cations’’ Chem. Eur. J. 22, 2417-2426. [13] V. Novakova, M. Laskova, H. Vavrickova, P. Zimcik, 2015. ‘’Phenol Substituted Tetrapyrazinoporphyrazines: pH Dependent Fluorescence in Basic Media’’ Chem. Eur. J. 21 14382-14392. [14] I.V. Nesterova, C.A. Bennett, S.S. Erdem, R.P. Hammer, P.L. Deininger, S.A. Soper, 2011. ‘’Near-IR single fluorophore quenching system based on phthalocyanine (Pc) aggregation and its application for monitoring inhibitor/activator action on a therapeutic target: L1-EN’’ Analyst 136 1103-1105. [15] P. Zimcik, V. Novakova, K. Kopecky, M. Miletin, R.Z. Uslu Kobak, E. Svandrlikova, 2012. ‘’Magnesium azaphthalocyanines: an emerging family of excellent red-emitting fluorophores’’ Inorg. Chem. 51 4215-4223. [16] D. Wohrle, G. Schnurpfeil, S.G. Makarov, A. Kazarin, O.N. Suvorova, 2012. ‘’ Practical Applications of Phthalocyanines – from Dyes and Pigments to Materials for Optical, Electronic and Photo-electronic Devices’’ Macroheterocycles 5 191-202.[17] P. Zimcik, A. Malkova, L. Hruba, M. Miletin, V. Novakova, 2017. ‘’Bulky 2,6-diphenylphenylsulfanyl substituents efficiently inhibit aggregation in phthalocyanines and tetrapyrazinoporphyrazines and control their photophysical and electrochemical properties’’ Dyes and Pigments 136 715-723.[18] T.W. Lin, S.D. Huang, 2001. ‘’Direct and simultaneous determination of copper, chromium, aluminum and manganese in urine with a multielement graphite furnace atomic absorption spectrometer’’ Anal. Chem. 73 (17) 4319-4325.[19] C.N. Sawyer, P.L. McCarty, G.F. Parkin, Chemistry for Environmental Engineering, fourth ed., McGraw-Hill, New York, 1996, p. 634. [20] L. Feng, Y. Zhang, L. Wen, Z. Shen, Y. Guan, 2011. ‘’Colorimetric determination of copper (II) ions by filtration on sol-gel membrane doped with diphenylcarbazide’’ Talanta 84 (3) 913-917. [21] C. Pfeiffer, R. Mailloux, 1987. ‘’Excess copper as a factor in human diseases’’ J. Orthomol. Med. 2 (3) 171-182. [22] Yamini, Y., Hassan, J., Karbasi, M.H. 2004. ‘’Solid phase extraction of copper and cupron on octadecyl silica cartridge and its determination with atomic absorption spectrometry’’ Microchim. Acta 148 (3-4) 305-309. [23] Alkan, D., Kara, M. 2002. ‘’Preconcentration and separation of copper(II) with solvent extraction using N,N0 -bis(2-hydroxy-5- bromo-benzyl) 1,2 diaminopropane, Microchem. J. 71 29-39. [24] Tobiasz, A., Walas, S., Soto Hernandes, A., Mrowiec, H. 2012. ‘’Application of multiwall carbon nanotubes impregnated with 5- dodecylsalicylaldoxime for on-line copper preconcentration and determination in water samples by flame atomic absorption spectrometry’’ Talanta 96 89-95. [25] Gao, Y., Wu, P., Li, W., Xuan, Y., Hou, X. 2010. ‘’Simultaneous and selective preconcentration of trace Cu and Ag by one-step displacement cloud point extraction for FAAS determination’’ Talanta 81 586-590. [26] Alver, E., Demirci, A., Ozcimder, M. 2012. ‘’Microextraction methods’’ Sigma J. Eng. Nat. Sci. 30 75-90. [27] Kandhro, G., Soylak, M., Kazı, T.G., Yılmaz, E. 2014. ‘’Enrichment of copper as 1-(2-pyridylazo)-2-naphthol complex by the combination of dispersive liquid-liquid micro-extraction/flame atomic absorption spectrometry’’ J. AOAC Int. 97 205-210. [28] Stanisz, E., Zgola-Grzeskowiak, A. 2013. ‘’In situ metathesis ionic liquid formation dispersive liquid-liquid microextraction for copper in water samples by electrothermal atomic absorption spectrometry’’ Talanta 115 178-183. [29] Baghdadi, M., Shemirani, F. 2008 ‘’Cold-induced aggregation microextraction: a novel sample preparation technique based on ionic liquids’’ Anal. Chim. Acta 613 56-63.[30] Çağlar, Y., Saka, E.T., Alp, H., Kantekin, H., Ocak, Ü., Ocak, M. 2016. ‘’A Simple Spectrofluorimetric Method Based on Quenching of a Nickel(II)-Phthalocyanine Complex to Determine Iron (III)’’ Journal of Fluorescence 26 1381-1389.

Details

Primary Language English
Subjects Chemistry, Analytical
Journal Section Research Articles
Authors

Yasemin ÇAĞLAR> (Primary Author)
Giresun University
0000-0002-8437-5373
Türkiye


Ece Tugba SAKA>
Karadeniz Technical University
Türkiye

Publication Date December 11, 2019
Application Date November 18, 2019
Acceptance Date December 2, 2019
Published in Issue Year 2019, Volume 1, Issue 1

Cite

Bibtex @research article { turkjac648118, journal = {Turkish Journal of Analytical Chemistry}, eissn = {2687-6698}, address = {Karadeniz Teknik Üniversitesi, Fen Fakültesi, Kimya Bölümü, Oda No: 111, 61080 Trabzon}, publisher = {Miraç OCAK}, year = {2019}, volume = {1}, number = {1}, pages = { - }, title = {A novel silicone phthalocyanine for the preconcentration and spectrophotometric determination of copper by ionic liquid-based dispersive liquid-liquid microextraction}, key = {cite}, author = {Çağlar, Yasemin and Saka, Ece Tugba} }
APA Çağlar, Y. & Saka, E. T. (2019). A novel silicone phthalocyanine for the preconcentration and spectrophotometric determination of copper by ionic liquid-based dispersive liquid-liquid microextraction . Turkish Journal of Analytical Chemistry , 1 (1) , . Retrieved from https://dergipark.org.tr/en/pub/turkjac/issue/50574/648118
MLA Çağlar, Y. , Saka, E. T. "A novel silicone phthalocyanine for the preconcentration and spectrophotometric determination of copper by ionic liquid-based dispersive liquid-liquid microextraction" . Turkish Journal of Analytical Chemistry 1 (2019 ): <https://dergipark.org.tr/en/pub/turkjac/issue/50574/648118>
Chicago Çağlar, Y. , Saka, E. T. "A novel silicone phthalocyanine for the preconcentration and spectrophotometric determination of copper by ionic liquid-based dispersive liquid-liquid microextraction". Turkish Journal of Analytical Chemistry 1 (2019 ):
RIS TY - JOUR T1 - A novel silicone phthalocyanine for the preconcentration and spectrophotometric determination of copper by ionic liquid-based dispersive liquid-liquid microextraction AU - YaseminÇağlar, Ece TugbaSaka Y1 - 2019 PY - 2019 N1 - DO - T2 - Turkish Journal of Analytical Chemistry JF - Journal JO - JOR SP - EP - VL - 1 IS - 1 SN - -2687-6698 M3 - UR - Y2 - 2019 ER -
EndNote %0 Turkish Journal of Analytical Chemistry A novel silicone phthalocyanine for the preconcentration and spectrophotometric determination of copper by ionic liquid-based dispersive liquid-liquid microextraction %A Yasemin Çağlar , Ece Tugba Saka %T A novel silicone phthalocyanine for the preconcentration and spectrophotometric determination of copper by ionic liquid-based dispersive liquid-liquid microextraction %D 2019 %J Turkish Journal of Analytical Chemistry %P -2687-6698 %V 1 %N 1 %R %U
ISNAD Çağlar, Yasemin , Saka, Ece Tugba . "A novel silicone phthalocyanine for the preconcentration and spectrophotometric determination of copper by ionic liquid-based dispersive liquid-liquid microextraction". Turkish Journal of Analytical Chemistry 1 / 1 (December 2019): - .
AMA Çağlar Y. , Saka E. T. A novel silicone phthalocyanine for the preconcentration and spectrophotometric determination of copper by ionic liquid-based dispersive liquid-liquid microextraction. TurkJAC. 2019; 1(1): -.
Vancouver Çağlar Y. , Saka E. T. A novel silicone phthalocyanine for the preconcentration and spectrophotometric determination of copper by ionic liquid-based dispersive liquid-liquid microextraction. Turkish Journal of Analytical Chemistry. 2019; 1(1): -.
IEEE Y. Çağlar and E. T. Saka , "A novel silicone phthalocyanine for the preconcentration and spectrophotometric determination of copper by ionic liquid-based dispersive liquid-liquid microextraction", Turkish Journal of Analytical Chemistry, vol. 1, no. 1, Dec. 2019