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Organic core–shell-shaped micro/nanoparticles from twisted macrocycles in Schiff base reaction

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Abstract

Functional self-assemblies derived from noncovalent interactions such as lipid vesicles and DNA chiral double helices are a typical feature of natural life activity. Because of this phenomenon, a self-assembly approach for various functional organic particles is a desirable objective in supramolecular chemistry. Here, we report the discovery of enantiomeric conformers from a twisted macrocyclic host (MH), which was obtained from an achiral precursor by Schiff base reaction. Further studies suggest that a series of unexpected and stable core–shell-based organic micro/nanospheres can be directly precipitated from a simple reaction solution with high yield. A single-crystal X-ray diffraction analysis of MH revealed that the unusual C–H⋯π interaction triggered self-assembly of the enantiomeric forms in the solid state plays an important role in the formation of the core–shell-shaped organic particles.

Graphical abstract: Organic core–shell-shaped micro/nanoparticles from twisted macrocycles in Schiff base reaction

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Publication details

The article was received on 27 Aug 2018, accepted on 13 Oct 2018 and first published on 15 Oct 2018


Article type: Edge Article
DOI: 10.1039/C8SC03824D
Citation: Chem. Sci., 2019, Advance Article
  • Open access: Creative Commons BY license
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    Organic core–shell-shaped micro/nanoparticles from twisted macrocycles in Schiff base reaction

    H. Chen, C. Huang, Y. Ding, Q. Zhang, B. Zhu and X. Ni, Chem. Sci., 2019, Advance Article , DOI: 10.1039/C8SC03824D

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