Self-Sorting of Two Hydrocarbon Receptors with One Carbonaceous Ligand

Taisuke Matsuno, Sota Sato, Atsutoshi Yokoyama, Sho Kamata, Hiroyuki Isobe

    Research output: Contribution to journalArticle

    21 Citations (Scopus)

    Abstract

    Non-directional van der Waals forces in biological and synthetic supramolecular systems play important roles in molecular assembly, particularly in determining the distances of the interacting species. The van der Waals forces are normally used in combination with other directional forces and are considered to play a secondary role in achieving specificity and fidelity in molecular recognition. Using an ideal supramolecular system consisting solely of hydrogen and carbon atoms, we found that the van der Waals interactions enable the high-fidelity sorting of two homomeric receptors during ligand-induced assembly. The self-sorting occurred in a narcissistic manner by repulsion of a competing diastereoisomeric receptor from the assembly. The structure–sorting relationship study with enantiomers further revealed the dominant role of the van der Waals forces in shape recognition for high-fidelity self-sorting.

    Original languageEnglish
    Pages (from-to)15339-15343
    Number of pages5
    JournalAngewandte Chemie - International Edition
    Volume55
    Issue number49
    DOIs
    Publication statusPublished - 2016

    Keywords

    • fullerenes
    • molecular recognition
    • nanotubes
    • receptors
    • self-sorting

    ASJC Scopus subject areas

    • Catalysis
    • Chemistry(all)

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