Chiral Metal–Organic Framework with Temperature-Dependent Homochirality for Chiral Discrimination

• Published in: Analytical chemistry (Washington) Vol. 95; no. 15; pp. 6467 - 6475
• Main Authors: Liu, Ning, Li, Junyao, Cai, Wenrong, Wu, Datong, Kong, Yong
• Format: Journal Article
• Language: English
• Published: United States American Chemical Society 18.04.2023
• Subjects: Chemistry; Chirality; Isomers; Metal ions; Metal-organic frameworks; Phenylalanine methyl ester; Porphyrins; Temperature dependence; Tryptophan
• ISSN: 0003-2700; 1520-6882
• DOI: 10.1021/acs.analchem.3c01316

Chiral metal–organic frameworks (CMOFs) have attracted considerable attention in chiral discrimination and separation. In this work, a simple CMOF is synthesized through a facile one-pot method by using Zn­(II), tetra­(4-carboxyphenyl)-porphyrin (TCPP), and d-phenylalanine methyl ester (d-Phe-OMe) as metal ion, organic ligand, and chiral source, respectively. Interestingly, the CMOFs synthesized at different temperatures (25 and 160 °C) display quite different morphologies and diametrically opposite chirality due to the different interaction modes between TCPP and d-Phe-OMe at 25 and 160 °C. Next, the CMOFs synthesized at 25 and 160 °C are utilized for the chiral discrimination of the isomers of tryptophan (Trp), resulting in exactly the reverse effect. The developed CMOF-based chiral sensors also exhibit excellent reproducibility, suggesting their great potential for chiral analysis.