Novel axially disubstituted non-aggregated silicon phthalocyanines

This paper describes the synthesis, spectroscopic characterization of a range of new axially-disubstituted silicon phthalocyanines with 2-[2-(dimethylamino)ethoxy] or 2-[2-(1,4,7,10,13-pentaoxa-16-azacyclooctadecan-16-yl)ethoxy] groups as axial ligands. 2-[2-(Dimethylamino)ethoxy]ethanol 2, 2-[2-(1,4,7,10,13-pentaoxa-16-azacyclooctadecan-16-yl)ethoxy]ethanol 4 are reacted with silicon phthalocyanine 1, to give an axially-disubstituted silicon phthalocyanines 3 and 5. Axially-disubstituted silicon phthalocyanine complexes were synthesized at the first time. Newly synthesized silicon phthalocyanines were characterized by UV–Vis, IR, 1H NMR, 13C NMR spectroscopy, ESI mass spectrometry. These new silicon(IV) phthalocyanines 3 and 5 showed excellent solubility in organic solvents such as CHCl3, CH2Cl2, acetone, DMF, DMSO, THF, EtOAc. The aggregation behavior of these compounds were investigated in different concentrations of DMSO. The effect of solvents on absorption spectra were studied in various organic solvents. The thermal stabilities of the silicon(IV) phthalocyanines 3 and 5 were determined by thermogravimetric analysis.

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► Synthesis and characterization of axially disubstituted silicon phthalocyanines.
► Thermal properties of non-aggregated silicon phthalocyanines.
► Investigation of aggregation behaviors of highly soluble silicon phthalocyanines in different solvents and concentrations.