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Issue 25, 2012
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Supramolecular polymerization of oligopyrenotides – stereochemical control by single, natural nucleotides

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Abstract

Amphiphilic heptapyrenotides (Py7) assemble into supramolecular polymers. Here we present a comprehensive spectroscopic study of aggregates and co-aggregates of the non-chiral Py7 and its mono- or di-substituted nucleotide analogs (Py7-N and N-Py7-N′). The data show that the formation of supramolecular polymers from oligopyrenotides is highly sensitive to the nature of the attached, chiral auxiliary. A single natural nucleotide may be sufficient for the fine tuning of the aggregates’ properties by changing the mechanism of aggregation from an isodesmic to a nucleation–elongation process, which results in a high degree of amplification of chirality in the formed supramolecular polymers. Watson–Crick complementarity does not play a significant role, since co-aggregates of oligomers modified with complementary nucleotides show no signs of supramolecular polymerization. Depending on the nucleotide, the helical sense of the polymers is shifted to an M-helix or a P-helix. The findings demonstrate the value of oligopyrenotides as oligomeric building blocks for the generation of optically active supramolecular polymers.

Graphical abstract: Supramolecular polymerization of oligopyrenotides – stereochemical control by single, natural nucleotides

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Publication details

The article was received on 13 Feb 2012, accepted on 01 May 2012 and first published on 02 May 2012


Article type: Paper
DOI: 10.1039/C2OB25320H
Citation: Org. Biomol. Chem., 2012,10, 4891-4898
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    Supramolecular polymerization of oligopyrenotides – stereochemical control by single, natural nucleotides

    A. L. Nussbaumer, F. Samain, V. L. Malinovskii and R. Häner, Org. Biomol. Chem., 2012, 10, 4891
    DOI: 10.1039/C2OB25320H

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