Design,synthesis And Application Of Phthalocyanine Imide-Based Electron Acceptors And Photodynamic Therapy Molecules

Phthalocyanine derivatives with large conjugated systems are widely studied in the field of organic semiconductors and photodynamic therapy,owing to their strong absorption,high stability,and convenient modification.Strong aggregation and poor solubility deriving from the rigid conjugated core greatly limit their potential applications.In this study,we focus on the development and application of phthalocyanine compounds,a series of novel phthalocyanine and naphthalocyanine imide molecules were designed,synthesized and applied to organic solar cells or photodynamic therapy.The specific research work is as following.1.Design,synthesis and photovoltaic application of phthalocyanine imide based acceptor materials.In this study,asymmetric zinc phthalocyanine imide compounds were synthesized from o-xylene,and two zinc phthalocyanine imide compounds 9a and 9b with twisted structures were synthesized by Stille coupling reactions with thiophene and bithiopheneπ-bridges.They exhibited strong absorption in the 600-900 nm,low aggregation,and deep lowest unoccupied molecular orbital（LUMO）energy level（-4.05 e V）.They are expected to be excellent electron acceptor.2.Design,synthesis and application of photodynamic therapy based on water-soluble silicon naphthalocyanine.In this study,two silicon naphthalocyanine with PEG₂₀₀₀ chains in the axial direction and four imides in the end groups were synthesized.We investigated the solubility,solution absorption,fluorescence,photothermal stability,and single-linear oxygen yields of such compounds in solution.The good solubility of these two molecules in water(10mg m L^-1),strong absorption at 700-900 nm,high fluorescence quantum yields（0.042,0.040）,good photostability and thermal stability（T_d>300 ^oC）and high single-linear oxygen yields（ФΔ=0.32,0.37）make these molecules promising for photodynamic therapy applications.In vitro evaluation results indicated that compound 18a can generate singlet oxygen in mouse breast cancer cells and effectively kill mouse breast cancer cells under light.