A Photosensitive Cationic Macrocycle Based on Triphenylamine as Photocatalysts for Selective Photooxidation of Phosphines, Styrenes, and Hydroazobenzenes

Abstract

Despite the fact that water provides significant benefits in decreased environmental pollution, low safety risks, and small costs of production, the application of water as a solvent in chemical reactions remains an ongoing challenge due to its lack of organophilicity and high polarity, hindering its efficiency and widespread application in organic synthesis. In this study, we have designed and synthesized a triphenylamine modified macrocyclic molecule, TPPB, which encompasses superior water solubility and outstanding efficiency and selectivity in generating singlet oxygen ( 1 O 2 ) under blue light irradiation in water. Furthermore, TPPB exhibits excellent efficiency in facilitating the photooxidation of phosphines, styrenes, and also hydroazobenzenes in water with remarkable stability and versatility. This study presents an approach for creating macrocyclic photosensitizers, expanding the use of macrocyclic molecules in the realm of photocatalytic organic processes.

Tetraphenylethylene-based photoresponsive supramolecular organic framework and its metallization for photocatalytic redox reactions

“…Subsequently, its photocatalytic activity in the oxidative reaction of 1,2-diphenylhydrazine in water was also studied. 62,63 As shown in Table S1,† the assembled SOF as a photocatalyst in the water-based solution led to a significant yield of 86% (entry 1) when irradiated by UV light at room temperature, whereas the monomers MV-DPY and NA-TPE showed lower yields (no reaction, entry 2 and 33%, entry 3). In addition, it was noted that reducing the concentration of SOF to 0.5 mol% decreased the catalytic yield to 54% (entry 4).…”