Triazole Substituted Phthalocyanines and Their Electrochemical Properties


New cobalt (II), zinc (II), tin (II) and metal free phthaloyanines having peripherally triazole and Schiff’s base groups on were synthesized and their electrochemical properties were studied. In the first step of the synthetic procedure, triazole moiety, in the second step Shiff base moiety and in the third step key compound substituted phthalonitrile have been synthesized successfully in high yield. At the final stage target phthalocyanines have been obtained and characterized by combination of spectral analysis. The electrochemical measurements showed that while Free- and Sn-Pc give irreversible oxidation process, Co- and Zn- phthalocyanines give quasi-reversible electron transfer reaction in dichloromethane solution.


Phthalocyanine; Metallophthalocyanine; Triazole; Schiff base; Electrochemistry.

DOI: 10.17350/HJSE19030000071

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1. Kobayashi N. Optically active phthalocyanines. Coord. Chem. Rev. 99 (2001) 219-221.

2. Dede G, Bayrak R, Er M, Özkaya AR, Değirmencioğlu İ. DBU-catalyzed condensation of metal free and metallophthalocyanines containing thiazole and azine moieties: Synthesis, characterization and electrochemical properties. Journal of Organometallic Chemistry 740 (2013) 70-77.

3. Bayrak R, Dumludağ F, Akçay HT, Değirmencioğlu İ. Synthesis, characterization and electrical properties of peripherally tetra-aldazine substituted novel metal free phthalocyanine and its zinc(II) and nickel(II) complexes. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 105 (2013) 550-556.

4. Ledwaba M, Masilela N, Nyokong T, Antunes E. Surface modification of silica-coated gadolinium oxide nanoparticles with zinc tetracarboxyphenoxy phthalocyanine for the photodegradation of Orange G. Journal of Molecular Catalysis A: Chemical. 403 (2015) 64-76.

5. Uzunmehmetoğlu HZ, Yenilmez HY, Kaya K, Koca A, Altındal A, Bayır ZA. Electrochemical, Spectroelectrochemical, and Dielectric Properties of Metallophthalocyanines Bearing Redox Active Cobalt and Manganese Metal Centers. Inorganica Chimica Acta. 459 (2017) 51-62.

6. Patel NB, Khan IH, Rajani SD. Pharmacological evaluation and characterizations of newly synthesized 1,2,4-triazoles. European Journal of Medicinal Chemistry. 45 (2010) 4293-4299.

7. Kharb R, Sharma PC, Yar MS. Pharmacological significance of triazole scaffold. J. Enzyme Inhib. Med. Chem. 26 (2011) 1-21.

8. Maddila S, Pagadala R, Jonnalagadda SB. 1,2,4-Triazoles: A Review of Synthetic Approaches and the Biological Activity. Lett. Org. Chem. 10 (2013) 693-714.

9. Bekircan O, Menteşe E, Ulker S, Küçük Ç. Synthesis of Some New 1,2,4-Triazole Derivatives Starting from 3-(4-Chlorophenyl)-5-(4-methoxybenzyl)-4H-1,2,4-triazol with Anti-Lipase and Anti-Urease Activities. Archive Der Pharmazie. 347 (2014) 387-397.

10.Akçay HT, Çoruh U, Bayrak R, Menteşe E, Vazquez Lopez EM. A spectroscopic study on new phthalonitrile derivative and its computational background: 4-[(4,5-Diphenyl-4H-1,2,4-triazol-3-yl)sulfanyl]benzene-phthalonitrile. Journal of Molecular Structure. 1127 (2017) 539-548.

11.Khanmohammadi H, Abnosi MH, Hosseinzadeh A, Erfantalab M. Synthesis, biological and computational study of new Schiff base hydrazones bearing 3-(4-pyridine)-5-mercapto-1,2,4-triazole moiety. Spectrochim. Acta A 71 (2008) 1474-1480.

12. Li Z, Gu Z, Yin K, Zhang R, Deng Q, Xiang J. Synthesis of substituted-phenyl-1,2,4-triazol-3-thione analogues with modified D-glucopyranosyl residues and their antiproliferative activities. Eur. J. Med. Chem. 44 (2009) 4716-4720.

13. Bagihalli GB, Avaji PG, Patil SA, Badami PS. Synthesis, spectral characterization, in vitro antibacterial, antifungal and cytotoxic activities of Co(II), Ni(II) and Cu(II) complexes with 1,2,4-triazole Schiff bases. Eur. J. Med. Chem. 43 (2008) 2639-2649.

14 .Ferrer S, Haasnoot JG, Reedijk J, Muller E, Cingi MB, Lanfranchi M, Manotti AM, Ribas LJ. Trinuclear N,N-bridged copper(II) complexes involving a Cu3OH core: [Cu-3(mu(3)-OH)L(3)A(H2O)(2)]A center dot(H2O)(x) {L=3-acetylamino-1,2,4-triazolate; a = CF3SO3, NO3, ClO4; x = 0, 2} synthesis, X-ray structures, spectroscopy, and magnetic properties. Inorg. Chem. 39 (2000) 1859-1867.

15. Karaca H, Sezer S, Özalp-Yaman Ş, Tanyeli C. Concise synthesis, electrochemistry and spectroelectrochemistry of phthalocyanines having triazole functionality, Polyhedron. 72 (2014) 147-156.

16.Nas A, Fandaklı S, Kantekin H, Demirbaş A, Durmuş M. Novel organosoluble metal-free and metallophthalocyanines bearing triazole moieties: Microwave assisted synthesis and determination of photophysical and photochemical properties. Dyes and Pigments. 95 (2012) 8-17.

17.Demirbaş Ü, Kobak RZU, Akçay HT, Ünlüer D, Koca A, Çelik F, Kantekin H. Synthesis, characterization, electrochemical and spectroelectrochemical properties of novel peripherally tetra-1,2,4-triazole substituted phthalocyanines. Synthetic Metals. 215 (2016) 68-76.

18.Perrin DD, Armarego WLF. Purification of Laboratory Chemicals. Pergamon: Oxford; 1989.

19.Young GJ, Onyebuagu W. Synthesis and characterization of di-disubstituted phthalocyanines. J. Org. Chem. 55 (1990)

20. Yildirim N, Bekircan O. Use of ester formylhydrazones for the synthesis of 1,2,4-triazole and 1,3,4-oxadiazole derivatives. 37 (2013) 160-163.

21.Biyiklioglu Z, Bekircan O. Synthesis and electrochemical properties of axially disubstituted silicon phthalocyanine and peripherally tetra substituted manganese(III) phthalocyanine bearing 1,2,4-triazole substituents. Synthetic Metals. 200 (2014) 148-155.

22. Demirbaş Ü. Göl C, Barut B, Bayrak R, Durmuş M, Kantekin H, Değirmencioğlu İ. Peripherally and non-peripherally tetra-benzothiazole substituted metal-free zinc (II) and lead (II) phthalocyanines: Synthesis, characterization, and investigation of photophysical and photochemical properties. Journal of Molecular Structure. 1130 (2017) 677– 6 87.

23. Bayrak R, Akçay HT, Bıyıklıoğlu Z, Değirmencioğlu İ. Substituted phthalocyanines and their electropolymerization properties. Synthetic Metals. 220 (2016) 643–652.

24. Nas A, Kantekin H, Durmuş M, Gümrükçüoğlu N. Unmetallated and metallated phthalocyanines bearing oxadiazole groups: Synthesis, photophysical and photochemical studies. Journal of Luminescence. 154 (2014) 15–21.

25. Dilber G, Durmuş M, Kantekin H, Çakır V. Synthesis and characterization of a new soluble metal-free and metallophthalocyanines bearing biphenyl-4-yl methoxy groups. Journal of Organometallic Chemistry. 696 (2011) 2805–2814.

26. Demirbaş Ü, Pişkin M, Bayrak R, Ünlüer D, Dügdü E, Durmuş M, Kantekin H. The determination of photophysical and photochemical parameters of novel metal-free, zinc(II) and lead(II) phthalocyanines bearing 1,2,4- triazole groups. Synthetic Metals. 219 (2016) 76–82.

27.Demirbaş Ü, Pişkin M, Barut B, Bayrak R, Durmuş M, Kantekin H. Metal-free, zinc(II) and lead(II) phthalocyanines functioning with 3- (2H-benzo[d][1,2,3]triazol-2-yl)-4-hydroxyphenethyl methacrylate groups: Synthesis and investigation of photophysical and photochemical properties. Synthetic Metals. 220 (2016) 276–285.

28.Ghanem BS, Piskin M, Durmus M, El-Khouly ME, Al-Raqa SY. Synthesis, photophysical and photochemical properties of novel phthalocyanines substituted with triptycene moieties. Polyhedron. 90 (2015) 85–90.

29.Akçay HT, Piskin M, Demirbas Ü, Bayrak R, Durmus M ̧ Mentese E ̧ Kantekin H. Novel triazole bearing zinc(II) and magnesium(II) metallophthalocyanines: Synthesis, characterization, photophysical and photochemical properties. Journal of Organometallic Chemistry. 745-746 (2013) 379-386.

30. Demirbaş Ü, Akyüz D, Barut B, Bayrak R, Koca A, Kantekin H. Electrochemical and spectroelectrochemical properties of thiadiazole substituted metallo-phthalocyanines. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. 153 (2016) 71–78.

31.Demirbas Ü, Akçay HT, Koca A, Kantekin H. Synthesis, characterization and investigation of electrochemical and spectroelectrochemical properties of peripherally tetra 4-phenylthiazole-2-thiol substituted metal-free, zinc(II), copper(II) and cobalt(II) phthalocyanines. Journal of Molecular Structure. 1141 (2017) 643-649.

32. Demirbaş Ü, Akyüz D, Mermer A, Akçay HT, Demirbaş N, Koca A, Kantekin H. The electrochemical and spectroelectrochemical properties of metal free and metallophthalocyanines containing triazole/piperazine units. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. 153 (2016) 478–487.
How to Cite
Bayrak, R. (2017). Triazole Substituted Phthalocyanines and Their Electrochemical Properties. Hittite Journal of Science & Engineering, 5(1), 7-12. Retrieved from