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Phthalocyanine-based fluorescent chemosensor for the sensing of Zn (II) in dimethyl sulfoxide-acetonitrile

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Abstract

A tetra-substituted phthalocyanine based on 4-[2-(4-nitrophenoxy)ethoxy]phthalonitrile carrying nitrophenyl group for the sensing of Zn2+ has been prepared and characterized by elemental analysis, FT-IR, 1H and 13C NMR, and MS spectral data. The sensing of Zn2+ is based on the fluorescence quenching of Pc. Both absorbance and fluorescence spectra of ZnPc exhibit distinct changes in visible region in response to treatment with Zn2+ ion in dimethyl sulfoxide. The fluorescence spectrum of the ligand showed quenching in the intensity of the signal at 688 nm for Zn2+. The complex composition of ZnPc was found 1:1 by means of spectrophotometric and spectrofluorimetric titration data. The spectrofluorimetric method showed good sensitivity for Zn2+ with linear range and detection limit of 4.0 × 10−6–4.4 × 10−5 and 2.4×10−7 M, respectively.

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References

  1. Kobayashi, N.: Optically active phthalocyanines. Coord. Chem. Rev. 219–221, 99–123 (2001)

    Article  Google Scholar 

  2. Mc Keown, N.B.: Phthalocyanine-containing dendrimers. Adv. Mater. 11, 67–69 (1999)

    Article  CAS  Google Scholar 

  3. Bekaroğlu, Ö.: Synthesis of phthalocyanines and related compounds. J. Porphyrins Phthalocyanines 4, 465–473 (2000)

    Article  Google Scholar 

  4. Cook, M.J., Jafari-Fini, A.: Phthalocyanine-related macrocycles: cross cyclotetra-merisation products from 3, 4-dicyanothiophenes, 2, 3-dicyanothiophene and 3, 6-dialkylphthalonitriles. Tetrahedron 56, 4085–4094 (2000)

    Article  CAS  Google Scholar 

  5. Seotsanyana-Mokhosi, I., Kuznetsova, N., Nyokong, T.: Photochemical studies of tetra-2, 3-pyridinoporphyrazines. J. Photochem. Photobiol. A 140, 215–222 (2001)

    Article  CAS  Google Scholar 

  6. Sessler, J.L., Jayawickramarajah, J., Gouloumis, A., Torres, T., Guldi, D.M., Maldonado, S., Stevenson, K.J.: Synthesis and photophysics of a porphyrin–fullerene dyad assembled through Watson–Crick hydrogen bonding. Chem. Commun. 14, 1892–1894 (2005)

    Article  Google Scholar 

  7. Spikes, J.D.: Phthalocyanines as photosenstizers in biological systems and for the photodynamic therapy of tumors. Photochem. Photobiol. 43, 691–699 (1986)

    Article  CAS  Google Scholar 

  8. Drager, A.S., O’brien, D.F.: Novel synthesis of liquid crystalline phthalocyanines. J. Org. Chem. 65, 2257–2260 (2000)

    Article  CAS  Google Scholar 

  9. Leznoff, C.C., D’ Ascanio, A.M., Yıldız, S.Z.: Phthalocyanine formation using metals in primary alcohols at room temperature. J. Porphyrins Phthalocyanines 4, 103–111 (2000)

    Article  CAS  Google Scholar 

  10. Collins, R.A., Mohammed, K.A.: Gas sensitivity of some metal phthalocyanines. J. Phys. D: Appl. Phys. 21, 154–161 (1998)

    Article  Google Scholar 

  11. Amao, Y., Asai, K., Okura, I.: Fluorescence quenching oxygen sensor using an aluminum phthalocyanine–polystyrene film. Anal. Chim. Acta 407, 41–44 (2000)

    Article  CAS  Google Scholar 

  12. Kandaz, M., Yarasir, M.N., Koca, A.: Selective metal sensor phthalocyanines bearing non-peripheral functionalities: synthesis, spectroscopy, electrochemistry and spectroelectrochemistry. Polyhedron 28, 257–262 (2009)

    Article  CAS  Google Scholar 

  13. Kandaz, M., Güney, O., Senkal, F.B.: Fluorescent chemosensor for Ag(I) based on amplified fluorescence quenching of a new phthalocyanine bearing derivative of benzofuran. Polyhedron 28, 3110–3114 (2009)

    Article  CAS  Google Scholar 

  14. Liu, X., Qi, C., Bing, T., Cheng, X., Shangguan, D.: Highly selective phthalocyanine-thymine cojugate sensor for Hg2+ based on target induced aggregation. Anal. Chem. 81, 3699–3704 (2009)

    Article  CAS  Google Scholar 

  15. Bıyıklıoğlu, Z., Çakır, V., Koca, A., Kantekin, H.: Non-peripheral tetrasubstituted metal-free and metallophthalocyanines: Synthesis, electrochemical, in situ spectroelectrochemical and in situ electrocolorimetric characterization. Dyes Pigments 89, 49–55 (2011)

    Article  Google Scholar 

  16. Momoki, K., Sekino, J., Sato, H., Yamaguchi, N.: Theory of curved molar ratio plots and a new linear plotting method. Anal. Chem. 41, 1286–1299 (1969)

    Article  CAS  Google Scholar 

  17. Bourson, J., Valeur, B.: Ion-responsive fluorescent compounds. 2. Cation-steered intramolecular charge transfer in a crowned merocyanine. J. Phys. Chem. 93, 3871–3876 (1989)

    Article  CAS  Google Scholar 

  18. Van Nostrum, C.F., Picken, S.J., Schouten, A.J., Nolte, R.J.M.: Synthesis and supramolecular chemistry of novel liquid crystalline crown ether-substituted phthalocyanines: toward molecular wires and molecular ionoelectronics. J. Am. Chem. Soc. 117, 9957–9965 (1995)

    Article  Google Scholar 

  19. Ishii, K., Iwasaki, M., Kobayashi, N.: The Q absorption band of the excited triplet phthalocyanine dimer. Chem. Phys. Lett. 436, 94–98 (2007)

    Article  CAS  Google Scholar 

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Acknowledgment

This study was supported by the Research Fund of Karadeniz Technical University.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Sciences, Karadeniz Technical University, 61080, Trabzon, Turkey

    Yasemin Çağlar, Ece Tuğba Saka, Miraç Ocak, Halit Kantekin & Ümmühan Ocak

  2. Vocational School of Health Science, Karadeniz Technical University, 61080, Trabzon, Turkey

    Nurhan Gümrükçüoğlu

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  1. Yasemin Çağlar
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  2. Nurhan Gümrükçüoğlu
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  3. Ece Tuğba Saka
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  4. Miraç Ocak
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  6. Ümmühan Ocak
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Correspondence to Ümmühan Ocak.

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Çağlar, Y., Gümrükçüoğlu, N., Saka, E.T. et al. Phthalocyanine-based fluorescent chemosensor for the sensing of Zn (II) in dimethyl sulfoxide-acetonitrile. J Incl Phenom Macrocycl Chem 72, 443–447 (2012). https://doi.org/10.1007/s10847-011-0012-9

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  • DOI: https://doi.org/10.1007/s10847-011-0012-9

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