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Issue 35, 2019
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Chaperone-like chiral cages for catalyzing enantio-selective supramolecular polymerization

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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

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Publication details

The article was received on 17 May 2019, accepted on 29 Jul 2019 and first published on 30 Jul 2019


Article type: Edge Article
DOI: 10.1039/C9SC02412C
Chem. Sci., 2019,10, 8076-8082
  • Open access: Creative Commons BY license
    All publication charges for this article have been paid for by the Royal Society of Chemistry

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    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

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