Fluorinated/non-fluorinated triphenylamine axially substituted silicon phthalocyanine: Synthesis and photophysical properties

Abstract

Three novel fluorinated/ non-fluorinated triphenylamine axially substituted silicon phthalocyanines with AIE character were synthesized. They shows typical emission for phthalocyanine moieties at 678–688 nm as well as an emission at 396 nm for TPA moieties. • Three fluorinated/ non-fluorinated triphenylamine substituted silicon phthalocyanines with AIE character were synthesized and characterized. • Three molecules showed an typical emission for phthalocyanine moieties at 678–688 nm as well as an emission at 396 nm for TPA moieties. • Silicon phthalocyanines with fluorinated and triphenylamine substitutions possessed the highest fluorescence intensity, fluorescence quantum yield and singlet oxygen yield. • Silicon (IV) phthalocyanine with only triphenylamine (TPA) substitutions exhibited obviously AIE character in THF/water mixtures. Three novel fluorinated/non-fluorinated triphenylamine axially substituted silicon phthalocyanines (TPA-FBPA-SiPc, TPA-BPA-SiPc and TPA-SiPc) with aggreagtion-induced emission (AIE) character were synthesized by using silicon phthalocyanine (SiPc) as a core, triphenylamine (TPA) moieties as terminal groups, and fluorinate or non-fluorinate-bisphenol A as bridge groups. Such designed molecules showed typical emissions for SiPc at 675–688 nm as well as emissions for TPA moieties at 396 nm. Their photophysical and photochemical properties are affected by both the fluorinate-bisphenol A substitutions and TPA substitutions. TPA-FBPA-SiPc with both fluorinate-bisphenol A and TPA substitutions possessed the highest fluorescence intensity, fluorescence quantum yield as well as singlet oxygen yield. Besides, TPA-SiPc with only TPA substitutions could not only avoid the aggregation-caused quenching of phthalocyanines but also exhibite obvious AIE character in THF/water mixtures due to the presence of TPA moieties. This work could provide some useful structure and photophysical properties relationship for design novel phthalocyanine for photodynamic therapy.