Phenyl-Bis-Naphthyl Derivative-Based Artificial Light-Harvesting System for Singlet Oxygen Oxidation.

A novel artificial light-harvesting system (LHS) for the photooxidation reaction was constructed by the phenyl-bis-naphthyl derivative (PBN) and water-soluble phosphate-pillar[5]arene (WPP5). After host-guest interaction, WPP5 integrated with PBN to form WPP5-PBN amphiphiles, which self-assembled to WPP5-PBN nanoparticles. Based on the aggregate state of PBN in WPP5-PBN nanoparticles, WPP5-PBN nanoparticles emitted a significant yellow fluorescence as energy donors. Due to the yellow fluorescence fully covering the absorption of sulforhodamine 101 (SR101), SR101 was used as energy acceptors and loaded in WPP5-PBN nanoparticles for constructing the WPP5-PBN-SR101 LHS, whose energy transfer efficiency and antenna effect were 66.32% and 22.34. Notably, after the energy of the WPP5-PBN antenna transferred to SR101, more singlet oxygen (1O2) production was observed in the WPP5-PBN-SR101 LHS, which was successfully used as a photocatalyst to catalyze the oxidation reaction of 4-methoxythioanisole to 1-methoxy-4-(methylsulfinyl)benzene, imitating the solar energy conversion to chemical energy.