Magnesium(ii) 1-(1-adamantylsulfanyl)phthalocyanine – synthesis, photochemical and electrochemical properties†
Abstract
A mixed macrocyclization reaction of 3-(1-adamantylsulfanyl)-1,2-dicyanobenzene and 1,2-dicyanobenzene led to unsymmetrical magnesium(II) 1-(1-adamantylsulfanyl)phthalocyanine. The novel macrocycle was characterized using UV-Vis, MS MALDI and NMR spectroscopy. The spectroscopic study of solvatochromic effects indicated that the changes observed in the electronic absorption spectra are mainly a result of solvation, and that the coordinating strength of the solvent had little influence on the red shift. The novel magnesium(II) phthalocyanine derivative revealed in DMF and DMSO the fluorescence quantum yield (Φf) values of 0.30 and 0.35, and singlet oxygen quantum yield (ΦΔ) values of 0.32 and 0.25, respectively. The magnesium(II) phthalocyanine derivative displayed in the voltammetric study four sets of redox peaks, two one-electron oxidations, and two one-electron reductions, which were assigned to ring based one electron processes.