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 (<b>PBN</b>) and water-soluble phosphate-pillar[5]arene (<b>WPP5</b>). After host-guest interaction, <b>WPP5</b> integrated with <b>PBN</b> to form <b>WPP5-PBN</b> amphiphiles, which self-assembled to <b>WPP5-PBN</b> nanoparticles. Based on the aggregate state of <b>PBN</b> in <b>WPP5-PBN</b> nanoparticles, <b>WPP5-PBN</b> nanoparticles emitted a significant yellow fluorescence as energy donors. Due to the yellow fluorescence fully covering the absorption of sulforhodamine 101 (<b>SR101</b>), <b>SR101</b> was used as energy acceptors and loaded in <b>WPP5-PBN</b> nanoparticles for constructing the <b>WPP5-PBN-SR101</b> LHS, whose energy transfer efficiency and antenna effect were 66.32% and 22.34. Notably, after the energy of the <b>WPP5-PBN</b> antenna transferred to <b>SR101</b>, more singlet oxygen (¹O₂) production was observed in the <b>WPP5-PBN-SR101</b> 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.