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

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.

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Publication Details

Journal
European Journal of Organic Chemistry
Published
2025-05-19
DOI
https://doi.org/10.1002/ejoc.202500402
Primary Topic
Porphyrin and Phthalocyanine Chemistry
Type
article
Field-Weighted Citation Impact
0.00

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article

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

Yaoyu Liang, Rongxin Su, Yaohui Du, Yuefei Wang et al.
European Journal of Organic Chemistry
Porphyrin and Phthalocyanine Chemistry
article

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

Yaoyu Liang, Rongxin Su, Yaohui Du, Yuefei Wang, Bowen Li, Xuefeng Liu, Wei Dong Qi, Jiayu Liu
article en

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.

European Journal of Organic ChemistryVol. 28(27)
Tianjin University of Science and Technology (CN), China Automotive Technology and Research Center (CN), Tianjin Institute of Industrial Biotechnology (CN), Collaborative Innovation Center of Chemical Science and Engineering Tianjin (CN), State Key Laboratory of Chemical Engineering (CN)
National Natural Science Foundation of China, Tianjin University, State Key Laboratory of Chemical Engineering, Tianjin Municipal Science and Technology Bureau
Openalex Percentile: Top 93%
Porphyrin and Phthalocyanine Chemistry
DOIOpen Access PDFOpenAlex
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