In this study, the new 2-[2-(1 H -naphtho[1,2- e ][1,3]oxazin-2(3 H )-yl)ethoxy]ethanol, 6-(1 H -naphtho[1,2- e ][1,3]oxazin-2(3 H )-yl)hexan-1-ol have been synthesized. Then, novel axially naphthoxazin substituted two silicon(IV) phthalocyanines (SiPcs) have been synthesized and characterized. The aggregation behavior of SiPcs were examined in different solvents and concentrations in DMSO. In all studied solvents and concentrations, SiPcs were non-aggregated. The reduction and oxidation behavior of the axially disubstituted SiPcs were established by cyclic (CV) and square wave (SWV) voltammetry. Axially naphthoxazin substituted silicon(IV) phthalocyanines were observed to display phthalocyanine ring-based redox processes.