Register      Login
Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

A novel Schiff base-containing phthalocyanine and its azo dye-substituted analogue: the effect of pH on colour

Günay Kaya Kantar https://orcid.org/0000-0002-0259-0417 A *
+ Author Affiliations
- Author Affiliations

A Chemistry Department, Science and Literature Faculty, Recep Tayyip Erdoğan University, Rize, Türkiye.

* Correspondence to: gunay.kaya@erdogan.edu.tr

Handling Editor: Martyn Coles

Australian Journal of Chemistry 77, CH24014 https://doi.org/10.1071/CH24014
Submitted: 13 February 2024  Accepted: 22 May 2024  Published online: 13 June 2024

© 2024 The Author(s) (or their employer(s)). Published by CSIRO Publishing.

Abstract

There are many studies in the literature devoted to the synthesis of phthalocyanines substituted with Schiff bases and azo dyes and their particular properties. However, the comparison of spectral properties of these analogue compounds has not been investigated up to now. Therefore, a new eugenol group-bearing Schiff base-substituted zinc(II) phthalocyanine compound was synthesised and characterised and its UV/Vis spectral properties were compared with its azo dye analogue at different pH. It was determined that the azo dye analogue showed more pronounced spectral changes than the Schiff base-substituted phthalocyanine, depending on pH.

Keywords: azo dye, colour change, eugenol, imine group, pH, phthalocyanine, Schiff base, UV/Vis spectrum.

References

Lever ABP, Hempstead MR, Leznoff CC, Liu W, Melnik M, Nevin WA, et al. Recent studies in phthalocyanine chemistry. Pure Appl Chem 1986; 58: 1467-1476.
| Crossref | Google Scholar |

Lever AP. The phthalocyanines. Adv Inorg Chem Radiochem 1965; 7: 27-114.
| Crossref | Google Scholar |

Anthopoulos TD, Shafai TS. Oxygen induced p-doping of alpha-nickel phthalocyanine vacuum sublimed films: implication for its use in organic photovoltaics. Appl Phys Lett 2003; 82: 1628-1630.
| Crossref | Google Scholar |

Nazeeruddin MK, Humphry-Baker R, Gratzel M, Wohrle D, Schnurpfeil G, Schneider G, et al. Efficient near-IR sensitization of nanocrystalline TiO2 films by zinc and aluminum phthalocyanines. J Porphyr Phthalocya 1999; 3: 230-237.
| Crossref | Google Scholar |

Pannemann C, Dyakonov V, Parisi J, Hild O, Wohrle D. Electrical characterisation of phthalocyanine-fullerene photovoltaic devices. Synthetic Met 2001; 121: 1585-1586.
| Crossref | Google Scholar |

Sleven J, Gorller-Walrand C, Binnemans K. Synthesis, spectral and mesomorphic properties of octa-alkoxy substituted phthalocyanine ligands and lanthanide complexes. Mat Sci Eng C 2001; 18: 229-238.
| Crossref | Google Scholar |

Dini D, Barthel M, Hanack M. Phthalocyanines as active materials for optical limiting. Eur J Org Chem 2001; 2001: 3759-3769.
| Crossref | Google Scholar |

Kudrat-E-Zahan M, Haque MM. Synthesis, characterization and biological activity studies of mixed ligand complexes with schiff base and 2, 2’-bipyridine. Int J Appl 2019; 6: 2.
| Crossref | Google Scholar |

Akcay HT, Piskin M, Demirbas U, Bayrak R, Durmus M, Mentese E, et al. Novel triazole bearing zinc(II) and magnesium(II) metallo-phthalocyanines: synthesis, characterization, photophysical and photochemical properties. J Organomet Chem 2013; 745: 379-386.
| Crossref | Google Scholar |

10  Ashoor LS. Applications of biological of Azo-Schiff base ligand and its metal complexes and: a review. Almuthanna J Pure Sci 2021; 8(1): 74-90.
| Crossref | Google Scholar |

11  Slassi S, Fix-Tailler A, Larcher G, Amine A, El-Ghayoury A. Imidazole and azo-based Schiff bases ligands as highly active antifungal and antioxidant components. Heteroatom Chem 2019; 2019: 6862170.
| Crossref | Google Scholar |

12  Tuncel M, Serin S. Synthesis and characterization of copper(II), nickel(II) and cobalt(II) complexes with azo-linked Schiff base ligands. Synth. React. Inorg. Met.-Org. Nano-Met Chem 2005; 35: 203-212.
| Crossref | Google Scholar |

13  Tuncel M, Serin S, Tuncel M. Synthesis and characterization of new azo-linked Schiff bases and their cobalt(II), copper(II) and nickel(II) complexes. Transit Metal Chem 2006; 31: 805-812.
| Crossref | Google Scholar |

14  Ispir E. The synthesis, characterization, electrochemical character, catalytic and antimicrobial activity of novel, azo-containing Schiff bases and their metal complexes. Dyes Pigments 2009; 82: 13-19.
| Crossref | Google Scholar |

15  Ahmed IS, Moustafa MM, Abd El Aziz MM. Mono and binuclear Ag(I), Cu(II), Zn(II) and Hg(II) complexes of a new azo-azomethine as ligand: synthesis, potentiometric, spectral and thermal studies. Spectrochim Acta A 2011; 78: 1429-1436.
| Crossref | Google Scholar | PubMed |

16  Bayoumi HA, Alaghaz ANMA, Aljahdali MS. Cu(II), Ni(II), Co(II) and Cr(III) complexes with N2O2-chelating Schiff’s base ligand incorporating azo and sulfonamide moieties: spectroscopic, electrochemical behavior and thermal decomposition studies. Int J Electrochem Sci 2013; 8: 9399-9413.
| Crossref | Google Scholar |

17  Towns AD. Developments in azo disperse dyes derived from heterocyclic diazo components. Dyes Pigments 1999; 42: 3-28.
| Crossref | Google Scholar |

18  Kantar C, Mert F, Sasmaz S. Microwave-assisted synthesis and characterization of phthalocyanines substituted with azo compound containing eugenol moiety. J Organomet Chem 2011; 696: 3006-3010.
| Crossref | Google Scholar |

19  Yenilmez HY, Okur AI, Gul A. Peripherally tetra-palladated phthalocyanines. J Organomet Chem 2007; 692: 940-945.
| Crossref | Google Scholar |

20  Piskin M, Canpolat E, Ozturk OF. The new zinc phthalocyanine having high singlet oxygen quantum yield substituted with new benzenesulfonamide derivative groups containing Schiff base. J Mol Struct 2020; 1202: 127181.
| Crossref | Google Scholar |

21  Yuzeroglu M, Karaoglan GK, Kose GG, Erdogmus A. Synthesis of new zinc phthalocyanines including schiff base and halogen; photophysical, photochemical, and fluorescence quenching studies. J Mol Struct 2021; 1238: 130423.
| Crossref | Google Scholar |

22  Nejati K, Rezvani Z, Massoumi B. Syntheses and investigation of thermal properties of copper complexes with azo-containing Schiff-base dyes. Dyes Pigments 2007; 75: 653-657.
| Crossref | Google Scholar |

23  Kantar C, Akal H, Kaya B, Islamoglu F, Turk M, Sasmaz S. Novel phthalocyanines containing resorcinol azo dyes; synthesis, determination of pKa values, antioxidant, antibacterial and anticancer activity. J Organomet Chem 2015; 783: 28-39.
| Crossref | Google Scholar |

24  Zuo F, Liu XB. Synthesis and curing behavior of a novel benzoxazine-based bisphthalonitrile monomer. J Appl Polym Sci 2010; 117: 1469-1475.
| Crossref | Google Scholar |

25  Kantar C, Baltas N, Karaoglu SA, Sasmaz S. New potential monotherapeutic candidates for Helicobacter pylori: some pyridinazo compounds having both urease enzyme inhibition and anti-Helicobacter pylori effectiveness. Pharm Chem J 2021; 55: 246-252.
| Crossref | Google Scholar |

26  Bilgin A, Ertem B, Gok Y. Highly organosoluble metal-free phthalocyanines and metallophthalocyanines: synthesis and characterization. Eur J Inorg Chem 2007; 1703-1712.
| Crossref | Google Scholar |

27  Tikhomirova TV, Badaukayte RA, Kulinich VP, Shaposhnikov GP. Synthesis and study of properties of the sulfonaphthylazophenoxyphthalonitrile and related phthalocyanine. Russ J Gen Chem 2011; 81: 2355-2361.
| Crossref | Google Scholar |

28  Tikhomirova TV, Badaukaite RA, Kulinich VP, Shaposhnikov GP. Synthesis and properties of phthalonitriles with an azo chromophore and related phthalocyanines. Russ J Gen Chem 2013; 83: 116-123.
| Crossref | Google Scholar |

29  Ogunsipe A, Nyokong T. Effects of substituents and solvents on the photochemical properties of zinc phthalocyanine complexes and their protonated derivatives. J Mol Struct 2004; 689: 89-97.
| Crossref | Google Scholar |