Synthesis and electrochemistry of non-aggregated axially disubstituted silicon phthalocyanines bearing benzoxazin substituents

•Synthesis of axially disubstituted silicon phthalocyanines.•Investigation of aggregation behavior of silicon phthalocyanines.•Investigation of electrochemical studies of silicon phthalocyanines.

In this study, the new 2-{2-[6-(benzyloxy)-2H-1,3-benzoxazin-3(4H)-yl]ethoxy}ethanol, 6-[6-(benzyloxy)-2H-1,3-benzoxazin-3(4H)-yl]hexan-1-ol have been synthesized. Then, a series of new two axially disubstituted silicon(IV) phthalocyanines (SiPcs) bearing benzoxazin substituents have been synthesized and characterized. Synthesized axially di-substituted SiPcs showed good solubility in many organic solvents. The aggregation behavior of SiPcs was examined in different solvents and concentrations in DMSO. In all studied solvents, SiPcs were non-aggregated. Electrochemical properties of axially disubstituted SiPcs were determined with voltammetric (CV and SWV) measurements. Cyclic voltammetry showed three reduction couples and one oxidation couple for two axially disubstituted silicon(IV) phthalocyanines (SiPcs) bearing benzoxazin substituents.

Graphical abstractThe synthesis, aggregation and electrochemical properties of axially disubstituted silicon phthalocyanines bearing benzoxazin substituents are reported. In all studied solvents, SiPcs were non-aggregated. Electrochemical responses of SiPcs support the proposed structure of the complexes.Figure optionsDownload full-size imageDownload as PowerPoint slide