Vol.:(0123456789) 1 3 Journal of Inclusion Phenomena and Macrocyclic Chemistry https://doi.org/10.1007/s10847-019-00949-z ORIGINAL ARTICLE Substituted Co(II) and Cu(II) metallophthalocyanines from new Schif base containing pyrrole units: Synthesis, characterization and investigation of photocatalytic activity on 2,3‑dichlorophenol oxidation Ayse Aktas Kamiloglu 1  · Ece Tugba Saka 2  · Irfan Acar 3 Received: 11 July 2019 / Accepted: 4 October 2019 © The Author(s) 2019 Abstract In this article, novel Schif base compound 1 bearing pyrrole moiety has been synthesized from the reaction of 1-hydroxy- benzaldehyde with 1,2-aminophenylpyrrole for the frst time. The cobalt phthalocyanine and copper phthalocyanine (3–4) were prepared by the cyclotetramerization of the novel phthalonitrile compound 2 and the corresponding metal salts. The new phthalonitrile compound 2 was synthesized by the reaction between 4-((E)-{[2-(1H-pyrro-1-yl)phenyl]imino}methyl) phenol 1 and 4-nitrophthalonitrile in DMF. The all new compounds (1–4) have been characterized by FT-IR spectroscopy, 1 H-NMR/ 13 C-NMR, mass, UV–Vis spectroscopy techniques and elemental analysis (for metallophthalocyanines). Chlorine- bearing phenols are of a class of pollutants. They have been regarded as a potential risk to environment and human health. It is important to advanced efective techniques to remove chlorinated phenols in wastewater. For this purpose, we investigated that diferent parameters infuenced the photooxidation process were determined and 2,3-dichlorophenol oxidize to the less harmfull products with high conversion and yield in the presence of Cu(II) and Co(II) phthalocyanine catalysts. Keywords Metallophthalocyanine · Schif base · Pyrrole · 2,3-Dichlorophenol · Photocatalysis Introduction Phthalocyanines compounds (Pcs) have been consid- ered to be promising nominee due to their unique physi- cal, electronic and optical properties. Except for their use as dyes, Pcs have been broadly studied because they have been applied to many scientifc feld applications such as chemical sensors, catalysis, oxidation, electrochromic agents, semiconductors, photosensitizers for photodynamic cancer therapy (PDT), liquid crystals, nonlinear optics and solar energy conversion [1–5]. The chemical properties of the substitutent groups attached to the peripheral positions of phthalocyanine signifcantly afect the properties of Pcs, such as their solubility, aggregation, electronic absorption and photocatalysis properties [6]. Pyrrole itself is not naturally occurring. A lot of bioac- tive natural products (such as vitamin B 12 , bilirubin, por- phyrins and chlorophyll) and synthetic drugs contain a pyrrole moiety as their skeleton [7, 8]. They were found to possess a wide variety of biological activities such as anticancer, antifungal, antibacterial, anti-infammatory and antioxidants [9–16]. Schif bases derived bearing pyrrole moiety are effective many areas. Also, Schiff bases are known great interest due to their biological properties [17]. The mentioned facts about pyrrole group encouraged us to synthesize of new Schif base bearing pyrrole moiety and its metallophthalocyanines. Electronic supplementary material The online version of this article (https://doi.org/10.1007/s10847-019-00949-z) contains supplementary material, which is available to authorized users. * Ayse Aktas Kamiloglu ayse_aktas_kamiloglu@artvin.edu.tr; ayse_aktas@hotmail.com 1 Artvin Vocational School, Artvin Çoruh University, 08100 Artvin, Turkey 2 Department of Chemistry, Faculty of Science, Karadeniz Technical University, 61080 Trabzon, Turkey 3 Department of Energy Systems Engineering, Faculty of Technology, Karadeniz Technical University, 61830 Trabzon, Turkey