Synthesis, characterization and aggregation behaviour of novel peripherally tetra-substituted octacationic water soluble metal-free and metallophthalocyanines

  • Volkan Çakır
  • Dilek Çakır
  • Zekeriya Bıyıklıoğlu
  • Halit Kantekin
Original Article


In this study, a new phthalonitrile derivative 3 bearing 1,3-bis[3(dimethylamino)phenoxy]propan-2-ol 1, metal-free phthalocyanine (Pc) 4, metallophthalocyanines (MPcs) 57 and their quaternized derivatives 4a7a were synthesized. Metal-free Pc 4 was prepared by cyclotetramerization of phthalonitrile derivate 3 and MPcs 57 were synthesized by heating 3 with NiCl2, CoCl2 and CuCl2 in n-pentanol in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene, respectively. Quaternization of the dimethylamino functionality produced quaternized octacationic water soluble metal-free, Ni, Co and Cu Pcs which were soluble in water, DMF, DMSO. The aggregation behaviour of these compounds were investigated in different concentrations of chloroform for metal-free, Ni, Co and Cu Pcs. The effect of solvents on absorption spectra were studied in various organic solvents. The novel compounds were characterized using IR, 1H-, 13C NMR, UV–vis and MS spectral data.


Phthalocyanine Phthalonitrile Octacationic Quaternization Aggregation Water-soluble 



This study was supported by the Research Fund of Karadeniz Technical University, Project no: 8660 (Trabzon-Turkey).


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Copyright information

© Springer Science+Business Media Dordrecht 2012

Authors and Affiliations

  • Volkan Çakır
    • 1
  • Dilek Çakır
    • 1
  • Zekeriya Bıyıklıoğlu
    • 1
  • Halit Kantekin
    • 1
  1. 1.Department of Chemistry, Faculty of ScienceKaradeniz Technical UniversityTrabzonTurkey

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