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Issue 21, 2011
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Supramolecular chemistry of monochiral naphthalenediimides

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Abstract

Three new N-desymmetrised naphthalenediimides (NDIs) are described, each containing one chiral and one achiral centre. The ability of such ‘monochiral’ NDIs to self-assemble into hydrogen-bonded helical nanotubes, to act as a sergeant in a ‘sergeants-and-soldiers’ system and to form a hexameric receptor for C70 was examined. Small differences at the achiral centre were found to have significant effects on the supramolecular properties of the NDI. All three new NDIs form nanotubes that bind C60, but with different efficiencies, and one is a better sergeant than any of the dichiral NDIs investigated to date.

Graphical abstract: Supramolecular chemistry of monochiral naphthalenediimides

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Publication details

The article was received on 12 Jul 2011, accepted on 15 Aug 2011 and first published on 16 Aug 2011


Article type: Paper
DOI: 10.1039/C1OB06147J
Citation: Org. Biomol. Chem., 2011,9, 7547-7553
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    Supramolecular chemistry of monochiral naphthalenediimides

    T. W. Anderson, G. D. Pantoş and J. K. M. Sanders, Org. Biomol. Chem., 2011, 9, 7547
    DOI: 10.1039/C1OB06147J

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