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Substituted manganese phthalocyanines as bleach catalysts: synthesis, characterization and the investigation of de-aggregation behavior with LiCl in solutions

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Abstract

This study reported the oxidative degradation of morin dye with hydrogen peroxide catalyzed by manganese phthalocyanines as low temperature bleaching catalysts for laundry applications. A novel series of manganese phthalocyanines (MnPcs) have been synthesized starting with tetrakis[4-(1,3-dioxolan-2-yl)phenoxy)]phthalocyaninatomanganese(III) (2) prepared by the cyclotetramerization of 4-[4-(1,3-dioxolan-2-yl)phenoxy]-phthalonitrile (1). De-protection of acetal groups of 2 to the aldehyde group in an acetic acid/FeCl3 system yielded the tetrakis(4-formylphenoxy)phthalocyaninatomanganese(III) (3). The condensation of 3 with 3-(dimethylamino)-1-propylamine gave Schiff base-substituted Mn(III)Pc 4. Finally, quaternization of the dimethylamino functional groups with the reaction of methyl iodide produced cationic manganese(III) phthalocyanine 5 which was soluble in both DMSO and water. These new MnPcs were characterized by the combination of spectroscopic methods (FT-IR, UV–Vis and mass spectroscopy). The effects of structural variables of the prepared compounds (2–5) on their dissolution in the solvent system LiCl/DMAc-DMF-DMSO and THF were also investigated. Degradation of morin at 25 and 40 °C in the presence of catalysts (2–5)/H2O2 combination in basic medium was examined by online spectrophotometric method, and the bleaching activities of the prepared compounds have been evaluated comparatively. It was found that the prepared catalysts have more effective bleaching performance at 25 °C than tetraacetylethylenediamine (TAED) which is a bleach activator commercially used in powder detergent formulations.

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References

  1. P. Gregory, High-Technology Applications of Organic Colorants (Plenum Press, New York, 1991)

    Book  Google Scholar 

  2. N.B. McKeown, Phthalocyanine Materials: Synthesis, Structure, and Function (Cambridge University Press, Cambridge, 1998)

    Google Scholar 

  3. Y. Sadaokap, T.A. Göpel, W. Jones, Sens. Actuators A 1, 148 (1990)

    Article  Google Scholar 

  4. C.L. Lin, C.C. Lee, K.C. Ho, J. Electroanal. Chem. 524–525, 81 (2002)

    Article  Google Scholar 

  5. J. Simon, C. Sirlin, Pure Appl. Chem. 61, 1625 (1989)

    Article  CAS  Google Scholar 

  6. M. Emmelius, G. Pawlowski, H.W. Vollmann, Angew. Chem. 28, 1445 (1989)

    Article  Google Scholar 

  7. M. Hanack, D. Dini, M. Vagin, S. Barthel, Chem. Rec. 2, 129 (2002)

    Article  CAS  PubMed  Google Scholar 

  8. F. Matemadombo, S. Griveau, F. Bedioui, T. Nyokong, Electroanalysis 20, 1863 (2008)

    Article  CAS  Google Scholar 

  9. P.N. Mashazi, P. Westbroek, K.I. Ozoemena, T. Nyokong, Electrochim. Acta 53, 1858 (2007)

    Article  CAS  Google Scholar 

  10. N. Sehlotho, T. Nyokong, J. Electroanal. Chem. 595, 161 (2006)

    Article  CAS  Google Scholar 

  11. K. Kasuga, K. Tsuboi, M. Handa, T. Sugimori, K. Sogabe, Inorg. Chem. Commun. 2, 507 (1999)

    Article  CAS  Google Scholar 

  12. N. Chebotareva, T. Nyokong, Electrochim. Acta 42, 3519 (1997)

    Article  CAS  Google Scholar 

  13. H.A. Dincer, A. Koca, A. Gul, M.B. Kocak, Dyes Pigments 76, 825 (2008)

    Article  CAS  Google Scholar 

  14. S. Altun, Z. Odabaş, A. Altındal, A.R. Özkaya, Dalton Trans. 43, 7987 (2014)

    Article  CAS  PubMed  Google Scholar 

  15. I. Acar, R. Bayrak, E.T. Saka, Z. Bıyıklıoglu, H. Kantekin, Polyhedron 50, 345 (2013)

    Article  CAS  Google Scholar 

  16. E. Güzel, A. Atsay, S. Nalbantoglu, N. Saki, A.L. Dogan, A. Gül, M.B. Koçak, Dyes Pigments 97, 238 (2013)

    Article  CAS  Google Scholar 

  17. U. Michelsen, H. Kliesch, G. Schnurpfeil, A.K. Sobbi, D. Wohrle, Photochem. Photobiol. 64, 694 (1996)

    Article  CAS  PubMed  Google Scholar 

  18. M. Angelopoulos, Y. Liao, B. Furman, T. Graham, Mater. Res. Soc. Symp. Proc. 413, 637 (1996)

    Article  CAS  Google Scholar 

  19. A. Hebeish, M. Hashem, A. Higazy, Macromol. Chem. Phys. 202, 949 (2001)

    Article  CAS  Google Scholar 

  20. C. Xu, D. Hinks, A. El-Shafei, P. Hauser, M. Li, M. Ankeny, K. Lee, J. Fiber Bioeng. Inform. 4, 209 (2011)

    Article  Google Scholar 

  21. T. Wieprecht, J. Xia, U. Heinz, J. Dannacher, G. Schlingloff, J. Mol. Catal. A: Chem. 203, 113 (2003)

    Article  CAS  Google Scholar 

  22. H.W. Park, S.Y. Lee, J.B. Ahn, J. Suh, B. Kim, K. Lee, W.J. Kim, J. Surfactants Deterg. 9, 385 (2006)

    Article  CAS  Google Scholar 

  23. S. Tunc, T. Gurkan, O. Duman, J. Chem. Eng. 181–182, 431 (2012)

    Article  CAS  Google Scholar 

  24. D.D. Perrin, W.L.F. Armarego, D.R. Perrin, Purification of Laboratory Chemicals, 7th edn. (Pergamon Press, New York, 2013)

    Google Scholar 

  25. P. Sen, G.Y. Atmaca, A. Erdoğmuş, N. Dege, H. Genç, Y. Atalay, S.Z. Yildiz, J Fluoresc. 25, 1225 (2015)

    Article  CAS  PubMed  Google Scholar 

  26. P. Sen, S.Z. Yildiz, Inorg. Chim. Acta 462, 30 (2017)

    Article  CAS  Google Scholar 

  27. P. Sen, D.K. Simsek, S.Z. Yildiz, Appl. Organometal. Chem. 29, 509 (2015)

    Article  CAS  Google Scholar 

  28. G.K. Karaoglan, G. Gümrükçü, A. Koca, A. Gül, U. Avcıata, Dyes Pigments 90, 11 (2011)

    Article  CAS  Google Scholar 

  29. Y. Rio, M.S. Rodriguez-Morgade, T. Torres, Org. Biomol. Chem. 6, 1877 (2008)

    Article  CAS  PubMed  Google Scholar 

  30. T. Nyokong, Coord. Chem. Rev. 251, 1707 (2007)

    Article  CAS  Google Scholar 

  31. C. Nostrum, R.J.M. Nolte, Chem. Commun., 2385 (1996)

  32. M.J. Stillman, in Phthalocyanines: Properties and Applications, vol. 3, ed. by C.C. Leznoff, A.B.P. Lever (VCH, New York, 1993)

    Google Scholar 

  33. G.W.R. Canham, A.B.P. Lever, Inorg. Nucl. Chem. Lett. 9, 13 (1973)

    Article  Google Scholar 

  34. J. Janczak, R. Kubiak, M. Sledz, H. Borrmann, Y. Grin, Polyhedron 22, 2689 (2003)

    Article  CAS  Google Scholar 

  35. A.B.P. Lever, J.P. Wilshire, S.K. Quan, Inorg. Chem. 20, 761 (1981)

    Article  CAS  Google Scholar 

  36. P. Sen, F. Dumludag, B. Salih, A.R. Ozkaya, O. Bekaroglu, Synth. Met. 161, 1245 (2011)

    Article  CAS  Google Scholar 

  37. I. Yılmaz, New J. Chem. 32, 37 (2008)

    Article  Google Scholar 

  38. T. Keleş, D. Akyuz, Z. Biyiklioglu, A. Koca, Electroanalysis 29, 2125 (2017)

    Article  CAS  Google Scholar 

  39. R. Hage, A. Lienke, Angew. Chem. Int. Ed. 45, 206 (2006)

    Article  CAS  Google Scholar 

  40. A.B. Sorokin, E.V. Kudrik, Catal. Today 159, 37 (2011)

    Article  CAS  Google Scholar 

  41. W. Nam, H.J. Lee, S.-O. Oh, C. Kim, H.G. Jang, J. Inorg. Biochem. 80, 219 (2000)

    Article  CAS  PubMed  Google Scholar 

  42. A.B. Sorokin, S.D. Suzzoni-Dezard, D. Poullain, J.-P. Noe, B. Meunier, J. Am. Chem. Soc. 118, 7410 (1996)

    Article  CAS  Google Scholar 

  43. B.C. Gilbert, J.R.L. Smith, M.S. Newton, J. Oakes, R.P. Prats, Org. Biomol. Chem. 1, 1568 (2003)

    Article  CAS  PubMed  Google Scholar 

  44. P. Sen, N. Dege, S. Zeki Yildiz, J. Coord. Chem. 70, 2751 (2017)

    Article  CAS  Google Scholar 

  45. P. Sen, E. Yildirim, S. Zeki Yildiz, Synth. Met. 215, 41 (2016)

    Article  CAS  Google Scholar 

Download references

Acknowledgements

This work was supported by the Ministry of Science, Industry and Technology of Turkey (SANTEZ project no. 0182.STZ.2013-1) and Research Fund of Sakarya University (project nos. 2014-02-04 007 and 2015-50-02-036).

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Authors and Affiliations

  1. Department of Forensic Science, Faculty of Engineering and Natural Sciences, Uskudar University, 34662, Istanbul, Turkey

    Pinar Sen

  2. Department of Chemistry, Faculty of Arts and Sciences, Sakarya University, 54187, Sakarya, Turkey

    Pinar Sen & S. Zeki Yildiz

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  1. Pinar Sen
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  2. S. Zeki Yildiz
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Correspondence to Pinar Sen.

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Sen, P., Zeki Yildiz, S. Substituted manganese phthalocyanines as bleach catalysts: synthesis, characterization and the investigation of de-aggregation behavior with LiCl in solutions. Res Chem Intermed 45, 687–707 (2019). https://doi.org/10.1007/s11164-018-3637-0

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