A novel porphyrin derivative and its metal complexes: Electrochemical, photoluminescence, thermal, DNA-binding and superoxide dismutase activity studies

•4-Ethyl-2,6-bis(hydroxymethyl)phenol and 4-ethyl-2,6-diformylphenol compounds were characterized by X-ray crystallography.•A new porphyrin Schiff base ligand and its transition metal complexes have been synthesized.•First time, superoxide dismutase activity and DNA-binding properties of this type compounds were investigated.

In this study, a new porphyrin-Schiff base ligand (L) and its metal complexes (Cu(II), Fe(III), Mn(III), Pt(II) and Zn(II)) were synthesized. The starting material 4-ethyl-2,6-bis(hydroxymethyl)phenol (A) was synthesized from 4-ethylphenol and formaldehyde in the alkaline media. The compound (A) was then oxidized to the 4-ethyl-2,6-diformylphenol (B). The starting compounds (A) and (B) were obtained as single crystals. Structures of the compounds (A) and (B) were determined by the X-ray crytallography technique. The porphyrin ligand (L) and its metal complexes were characterized by the analytical and spectroscopic methods. Electronic, electrochemical and thermal properties of the synthesised compounds were investigated. Superoxide dismutase activities (SOD) of the porphyrin Schiff base complexes were investigated and results were discussed. Additionally, the DNA (fish sperm FSdsDNA) binding studies of the complexes were performed using UV–vis spectroscopy. Competitive studies with ethidium bromide (EB) show that the compounds interact efficiently with DNA through an intercalating way.

Graphical abstractIn this study, in order to synthesize the novel porphyrin Schiff base ligand, we prepared both 4-ethyl-2,6-bis(hydroxymethyl)phenol and 4-ethyl-2,6-diformylphenol compounds. The porphyrin Schiff base ligand is a novel compound. The compounds (A) and (B) were characterized by the analytical and spectroscopic methods. Single crystals of these compounds were obtained from the CHCl3–EtOH solution by the slow evaporation and their structural characterizations were, first time, done by X-ray crystallography technique.Figure optionsDownload full-size imageDownload as PowerPoint slide