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Amino‐Acid‐Encoded Enantioselective Photocatalysis in Self‐Assembled Porphyrin–Amino Acid Derivatives

Year: 2025

Type: article

Abstract: Porphyrin‐based nanomaterials have attracted much attention in photocatalysis due to their excellent photoelectrocatalytic ability and strong intermolecular interaction forces. Herein, a series of chiral assemblies of porphyrin–amino acid derivatives are prepared by linking different types of amino acids with terminal modifications to tetrakis(4‐carboxyphenyl)porphyrin via covalent bonding and their catalytic ability in enantioselective photocatalytic oxidation of tyrosine is investigated. The results show that the amino acid type and terminal groups significantly affect the macroscopic assembly morphology and microscopic chiral space of the porphyrin–amino acid derivatives, which is consistent with the results of molecular dynamics simulations and further impacts the rate and enantioselectivity of tyrosine chiral photocatalytic oxidation. These results provide new avenues for applying porphyrin derivatives in chiral photocatalysis.

Source: European Journal of Organic Chemistry

DOI: 10.1002/ejoc.202500402