Issue 35, 2019

Chaperone-like chiral cages for catalyzing enantio-selective supramolecular polymerization

Abstract

Cage catalysis has emerged as an important approach for mimicking enzymatic reactions by increasing the reaction rate and/or product selectivity of various types of covalent reactions. Here, we extend the catalytic application of cage compounds to the field of non-covalent molecular assembly. Acid-stable chiral imine cages are found to catalyze the supramolecular polymerization of porphyrins with an accelerated assembling rate and increased product enantioselectivity. Because the imine cages have a stronger interaction with porphyrin monomers and a weaker interaction with porphyrin assemblies, they can fully automatically detach from the assembled products without being consumed during the catalytic process. We reveal the kinetics of the auto-detachment of cages and the chirality growth of the assemblies using spectroscopic characterization studies. We find that the passivation groups attached to the cages are important for maintaining the structural stability of the cages during catalyzed assembly, and that the steric geometries of the cages can profoundly affect the efficiency of chiral regulation. This strategy demonstrates a new type of catalytic application of cage compounds in the field of molecular assembly, and paves the way to controlling supramolecular polymerization through a catalytic pathway.

Graphical abstract: Chaperone-like chiral cages for catalyzing enantio-selective supramolecular polymerization

Supplementary files

Article information

Article type
Edge Article
Submitted
17 May 2019
Accepted
29 Jul 2019
First published
30 Jul 2019
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2019,10, 8076-8082

Chaperone-like chiral cages for catalyzing enantio-selective supramolecular polymerization

Y. Wang, Y. Sun, P. Shi, M. M. Sartin, X. Lin, P. Zhang, H. Fang, P. Peng, Z. Tian and X. Cao, Chem. Sci., 2019, 10, 8076 DOI: 10.1039/C9SC02412C

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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