Autoamplification of Molecular Chirality through the Induction of Supramolecular Chirality

Authors

  • Derk Jan van Dijken,

    1. Center for Systems Chemistry, Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen (The Netherlands)
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  • Dr. John M. Beierle,

    1. Center for Systems Chemistry, Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen (The Netherlands)
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  • Dr. Marc C. A. Stuart,

    1. Center for Systems Chemistry, Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen (The Netherlands)
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  • Dr. Wiktor Szymański,

    1. Center for Systems Chemistry, Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen (The Netherlands)
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  • Prof. Dr. Wesley R. Browne,

    1. Center for Systems Chemistry, Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen (The Netherlands)
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  • Prof. Dr. Ben L. Feringa

    Corresponding author
    1. Center for Systems Chemistry, Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen (The Netherlands)
    • Center for Systems Chemistry, Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen (The Netherlands)===

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  • We thank Dr. P. de Mendoza and Dr. J. van Herpt for insightful comments and useful discussions. The European Research Council (Advanced Investigator grant 227897; B.L.F.), the Ministry of Education, Culture and Science of the Netherlands (Gravity program 024.001.035, B.L.F. and W.R.B.), and the US National Science Foundation (NSF International Postdoctoral Fellowship OISE-0853019, J.M.B.) are acknowledged for financial support.

Abstract

The novel concept for the autoamplification of molecular chirality, wherein the amplification proceeds through the induction of supramolecular chirality, is presented. A solution of prochiral, ring-open diarylethenes is doped with a small amount of their chiral, ring-closed counterpart. The molecules co-assemble into helical fibers through hydrogen bonding and the handedness of the fibers is biased by the chiral, ring-closed diarylethene. Photochemical ring closure of the open diarylethene yields the ring-closed product, which is enriched in the template enantiomer.

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