Novel polymeric phthalocyanines bridged flexible 1,5-pentanedithiol unit for metal ions extraction: synthesis, characterization and evaluation

  • Halil Zeki GökEmail author
  • Yaşar Gök
Original Article


A novel bisphthalonitrile 5,5′-(pentane-1,5-diylbis(sulfanediyl))bis(4-((2-aminophenyl)thio)phthalonitrile) 2 was synthesized by a nucleophilic aromatic substitution of chloro atom of 4-(2′-aminophenyl sulfanyl)-5-chloro-benzene-1,2-dicarbonitrile 1 with dithiol functions of pentane-1,5-dithiole. The synthesis of polymeric phthalocyanine complexes 3 and 4 by cyclotetramerization of bisphthalonitrile derivative 2 were accomplished in the presence of appropriate metal salt in a Schlenk tube containing quinoline under nitrogen atmosphere. The investigation of metal-ion binding properties of bisphthalonitrile 2 and polymeric zinc(II) phthalocyanine 4 was performed by using liquid–liquid extraction procedure for 2 and solid–liquid extraction procedure for 4. Polymeric zinc(II) phthalocyanine 4 was found to extract Ag(II) and Hg(II) with high efficiency. The novel compounds were characterized by a combination of elemental analysis and 1H NMR, 13C NMR, IR, and MS spectral data.


Bisphthalonitrile Polymeric phthalocyanine Metal ion extraction Dithiols 



One of us, HZG, is indebted to the Scientific & Technological Research Council of Turkey (TUBITAK) (Project No. KBAG 109T806) for the financial support. Murat Aslan, Ümit Akkoç and Arzu Meryem Deveci are also gratefully acknowledged for their assistance.

Supplementary material

10847_2019_901_MOESM1_ESM.doc (857 kb)
Supplementary material 1 (DOC 857 KB)


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Copyright information

© Springer Nature B.V. 2019

Authors and Affiliations

  1. 1.Department of Biomedical Engineering, Bucak Technology FacultyBurdur Mehmet Akif Ersoy UniversityBucakTurkey

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