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Issue 10, 2016
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Enantioselective assembly of amphipathic chiral polymer and racemic chiral small molecules during preparation of micro-scale polymer vesicles

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Abstract

Enantioselective assembly is observed during preparation of vesicles from a solution mixture of an amphipathic block copolymer bearing pendent chiral L- or D-phenylalanine groups in hydrophobic segments and racemic chiral small molecules. Primary experimental results reveal that racemic chiral small molecules have been enantioselectively encapsulated into the hydrophobic shells of assembled vesicles with homochiral bilayer membrane structure, showing reverse CD signals compared with the original vesicles. A further study shows that the enantiomeric excess obtained through the enantioselective assembly is directly dependent on the molecular weight of the hydrophobic chiral chain segments, implying both the hydrophobic interaction and chirality are key points during the assembly of vesicles. Other factors, such as hydrogen-bonding interactions and π–π stacking interaction, are also found to be responsible for the enantioselective assembly phenomenon during the formation of the vesicles.

Graphical abstract: Enantioselective assembly of amphipathic chiral polymer and racemic chiral small molecules during preparation of micro-scale polymer vesicles

  • This article is part of the themed collection: Polymers
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Publication details

The article was received on 07 Dec 2015, accepted on 24 Jan 2016 and first published on 25 Jan 2016


Article type: Paper
DOI: 10.1039/C5SM02957K
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Soft Matter, 2016,12, 2751-2756

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    Enantioselective assembly of amphipathic chiral polymer and racemic chiral small molecules during preparation of micro-scale polymer vesicles

    Y. Wang, Y. Zhuang, J. Gao, G. Zou and Q. Zhang, Soft Matter, 2016, 12, 2751
    DOI: 10.1039/C5SM02957K

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