Synthesis and photochemical properties of unsymmetrical phthalocyanine bearing two 1-adamantylsulfanyl groups at adjacent peripheral positions

A novel unsymmetrical magnesium(II) 2,3-bis(1-adamantylsulfanyl)phthalocyanine was prepared by mixed macrocyclization reaction of two phthalonitriles (phthalonitrile and 4,5-bis(1-adamantylsulfanyl)phthalonitrile) and characterized using UV–vis, MALDI MS and NMR methods. Precursor adamantyl disubstituted phthalonitrile was synthesized from 4,5-dichlorophthalonitrile. Absorption and emission properties of this novel phthalocyanine were investigated, including determination of fluorescence quantum yields, fluorescence lifetimes and solvatochromic effects. This newly synthesized phthalocyanine can be considered as a potential photosensitizer, as its singlet oxygen quantum yield (ΦΔ) of 0.49 was found in DMF and DMSO.