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.

Graphical abstractNew, unsymmetrical phthalocyanine bearing 1-adamantylsulfanyl moieties was synthesized, characterized and subjected to photochemical studies. The phthalocyanine was subjected to solvatochromic studies, and fluorescence quantum yields and fluorescence lifetimes were measured. Phthalocyanine was evaluated as potential photosensitizing agent by determining its ability to generate singlet oxygen.Figure optionsDownload full-size imageDownload as PowerPoint slideHighlights► Phthalocyanine with 1-adamantylsulfanyl moieties was synthesized and characterized. ► The fluorescence quantum yields and fluorescence lifetimes were measured. ► The singlet oxygen quantum yields were determined..