Document Type : Original Article (Special Issue)
Department of Science College of Basic Education, University of Sumer, Rifai, Iraq
Nickel (II) Phthalocynine (Ni-Pc) is a class of macro-cyclic compounds that has bivalent, tetradentade, planar, and 18 π-conjugated electron aromatic ring systems. Pcs are composed of four pyrrole units linked to four [aza] (—N=C—) groups at the α-carbon of [Pyrrole] unit and they have four aza bridges and four (phenylene) rings. This study aims to synthesize Nickel (II) Phthalocynine. The new synthesized product has been characterized by FT-IR and 1H-NMR spectroscopy. The procedure of this study includes the synthesis of Nickel (II) Phthalocynine (Ni-Pc) by the reaction of (o-cyanobenzamide) with Nickel that was powdered through heating. Different concentrations of Nickel (II) Phthalocynine were studied regarding the effect of antibacterial activity against two species of bacteria Escherichia coli and staphylococcus aureus by using disk-diffusion methods in Mueller–Hinton agar. The results of synthesis of Nickel (II) Phthalocynine shows a good resistance against the selected bacteria with “the minimum inhibitory concentration” (MIC) and “the minimum bactericidal concentration” (MBC) of (Ni-Pc).
Nickel (II) phthalocyanine (Ni-Pc) is one of Metallo-complex (M.Pc) which is a type of planar-molecule containing four groups of a [Pyrrole] ring linked to a benzene ring . This property gives (Ni-Pc) blue-green color at the region of (640-710 nm). Due to this advantage, Phthalocynine compound is among the important industrial dyes, and also they are related to the biological effective molecule (Chlorophyll) . It has been widely used in thin films because of the special chemical stability, a high electro-catalytic activity, and sensing applications by the supramolecular arrangement which is defined by many attributes of films such as thickness, morphology, and crystallinity. Therefore, it is assumed to be a highly arrangement molecule depends on metallic center atom . The (Ni-Pc) is tested to be applied in the solar cells as a transfer asset mediator . Likewise, it is used in the development of gas detector device due to its excellent thermal-chemical stabilities as a semiconductor property . Many new phthalocyanine derivatives compounds are being developed that characterize the new group on the semiconductor which limited the obtainable efficiency of photosensitizer chemical compounds . The major studies related to the synthesis of the substituted molecules are achieved from the chemical addition of amino, carboxylic, and hydroxyl groups as an extension of the center of macro-cyclic structure (Chenodeoxycholic acid). It has been tested for photovoltaic performance which rendered the highest efficiency of all reported phthalocyanine photosensitizers so far .
The Nickel (II) Phthalocynine (Ni-Pc) have the ability to create numbers of compound via collation with cations in the center with nitrogen pyrrolic substance and nickel compounds proved by many studies are very useful in the industry such as carbon nanotube due to the strong metal bonds, and also in the medical field as antitumor and antibacterial activity. Furthermore, it plays an important role in human body by increasing the inhabitation degree of medicine [8,9].
Materials and Methods
All ingredients and solvents were obtained from Aldrich and BDH Chemical Co. Gallen Kamp capillary melting point apparatus was used to measure melting points. (Bruker) tensor M27 spectrometer was used to take the FT-IR measurements. 1H-NMR spectra were collected in a Bruker spectrophotometer Ultra-shield at 400 MHz by using DMSO as an internal standard.
The reaction to get the final compound included two steps, as follow.
Preparation of [o-Cyanobenzamide]
The first step included the preparation of [o-Cyanobenzamide] by using 0.07 ml of [o-cyano benzoyl chloride] and it was added step by step till the end of amount to 30 ml of amine water solution at 6°C in 100 ml beaker . The solution was kept under a vigorous string for an hour. The mixture was left to be cooled for one hour, and then it was filtered by using [Büchner flask]. The residue was washed continuously with ice water till the pH indicator of washing water turned to 7 according to the pH meter. The solution was reflexed for 30 min and [o -Cyanobenzamide] was purified and recrystallized from hot water (1:50) ratio [11,12].
Preparation of Nickel (II) Phthalocynine (Ni-Pc)
The second step included the preparation of (Ni-Pc) by using 4 g of [o–Cyanobenzamide] from the first step, 1 g of powdered nickel, and 2.5 g of naphthalene (as diluent) were stirred heating up to 230 °C for one hour . Finally, 100 ml of acetone boiled for 5 min and the final powder product was treated by 1 M of sodium hydroxide diluted in hot water to remove the extra naphthalene [14, 15]. The residue was recrystallized from benzene.
Results and Discussions
The final compounds were synthesized according to mechanism exhibited in Scheme 1. The stretching vibration bands were at 1602.17-1644 cm-1 (C=N, C=C) and 3191.58 cm-1 (C-H aromatic). The I.R spectrum data and elemental analysis results were summarized in Table 1. The 1HNMR spectrum of [Ni-Pc] indicated the appearance of a broad singlet at the range of (7.5-8.04) P.P.M (12H, pc-CH), as listed in Table 2. The (Ni-Pc) of this study was tested against microorganisms type of bacteria by assessing of “inhibition zones”, “zone diameter”, and (MIC) values. As exhibited in the Table 3 and Figure 1, the results revealed a good resistance against the selected bacteria with “the minimum inhibitory concentration (MIC) and “the minimum bactericidal concentration” (MBC) .
Scheme 1: Mechanism of the (Ni-Pc)
Figure 1: Biological activity for Nickel (II) Phthalocynine
The preparation of Metallo-Phthalocynine from [o–Cyanobenzamide] was confirmed by using spectroscopic techniques (FT-IR and 1HNMR). The study of antibacterial activity led to terminate the activity of used types of bacteria.
This research did not receive any specific grant from fundig agencies in the public, commercial, or not-for-profit sectors.
All authors contributed to data analysis, drafting, and revising of the paper and agreed to be responsible for all the aspects of this work.
Conflict of Interest
There are no conflicts of interest in this study.
Osama S. Hashim
HOW TO CITE THIS ARTICLE
Osama S. Hashim. Synthesis, Characterization of Nickel (II) Phthalocynine, and Screening of Its Potential Antibacterial Activity. J. Med. Chem. Sci., 2022, 5(7) 1242-1246