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Issue 26, 2016
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Unexpected narcissistic self-sorting at molecular and supramolecular levels in racemic chiral calixsalens

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Abstract

The [3 + 3] cyclocondensation of 2-hydroxyisophthalaldehyde derivatives with racemic trans-1,2-diaminocyclohexane results in formation of triangular vase-like hexaimines called calixsalens. Calixsalen formation is highly stereoselective, yielding racemic mixtures that contain homochiral products with absolute configuration of either all-R or all-S at their stereogenic centres. Calixsalens form tail-to-tail dimers that are assembled into higher-order structures in the solid state. The formation of these dimers is accomplished by enantioselective self-recognition of chiral calixsalen units driven by non-covalent interactions only.

Graphical abstract: Unexpected narcissistic self-sorting at molecular and supramolecular levels in racemic chiral calixsalens

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Publication details

The article was received on 31 Jan 2016, accepted on 16 Mar 2016 and first published on 17 Mar 2016


Article type: Paper
DOI: 10.1039/C6CE00256K
Citation: CrystEngComm, 2016,18, 4996-5003
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    Unexpected narcissistic self-sorting at molecular and supramolecular levels in racemic chiral calixsalens

    M. Petryk, K. Biniek, A. Janiak and M. Kwit, CrystEngComm, 2016, 18, 4996
    DOI: 10.1039/C6CE00256K

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