Synthesis and photophysical properties of subphthalocyanine substituted with tetraphenylethylene moieties

Tetraphenylethylene-substituted phthalonitriles and corresponding subphthalocyanines have been synthesized. Mono- and di-substituted phthalonitriles could be prepared by a typical SNAr reaction. The crystallographic structures of phthalonitriles indicated that intermolecular [Formula: see text]-[Formula: see text] interactions were suppressed by the bulky tetraphenylethylene moieties. Subphthalocyanines substituted with tetraphenylethylenes at peripheral and axial positions were obtained by boron-templated macrocyclization of phthalonitriles. Phthalonitriles showed typical aggregation-induced-emission behavior in THF/water mixed solvents, while fluorescence intensities of subphthalocyanines were decreased with increasing water content.