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Self-Assembly of Semifluorinated Minidendrons Attached to Electron-Acceptor Groups into Pyramidal Columns

Authors

  • Virgil Percec Prof.,

    1. Roy&Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania, 19104-6323, USA, Fax: (+1) 215-573-7888
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  • Emad Aqad Dr.,

    1. Roy&Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania, 19104-6323, USA, Fax: (+1) 215-573-7888
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  • Mihai Peterca,

    1. Department of Physics and Astronomy, University of Pennsylvania, Philadelphia, Pennsylvania, 19104-6323, USA
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  • Mohammad R. Imam,

    1. Roy&Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania, 19104-6323, USA, Fax: (+1) 215-573-7888
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  • Martin Glodde Dr.,

    1. Roy&Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania, 19104-6323, USA, Fax: (+1) 215-573-7888
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  • Tusha K. Bera Dr.,

    1. Roy&Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania, 19104-6323, USA, Fax: (+1) 215-573-7888
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  • Yoshiko Miura Dr.,

    1. Roy&Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania, 19104-6323, USA, Fax: (+1) 215-573-7888
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  • Venkatachalapathy S. K. Balagurusamy Dr.,

    1. Roy&Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania, 19104-6323, USA, Fax: (+1) 215-573-7888
    2. Department of Physics and Astronomy, University of Pennsylvania, Philadelphia, Pennsylvania, 19104-6323, USA
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  • Paul C. Ewbank Dr.,

    1. Roy&Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania, 19104-6323, USA, Fax: (+1) 215-573-7888
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  • Frank Würthner Prof.,

    1. Institute of Organic Chemistry, University of Würzburg, 97074 Würzburg, Germany
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  • Paul A. Heiney Prof.

    1. Department of Physics and Astronomy, University of Pennsylvania, Philadelphia, Pennsylvania, 19104-6323, USA
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Abstract

The synthesis and self-assembly of twelve semifluorinated first-generation dendrons or minidendrons attached to electron-acceptor (n-type) groups generated from various combinations of eight acceptors and three dendrons are reported. Dendrons attached to small electron-acceptor molecules mediate their self-assembly into π-stacks located in the center of a supramolecular helical pyramidal column with the long axis of the acceptor perpendicular to the long axis of the column. Dendrons attached to large electron-acceptor molecules, such as perylene bisimide, mediate the assembly of their acceptors in an unprecedented arrangement of π-stacks that have the long axis of the acceptors parallel to the long axis of the supramolecular pyramidal column. All supramolecular columns self-organize into various periodic columnar arrays that exhibit liquid-crystalline phases, crystalline phases, or a liquid-crystalline phase with enhanced intracolumnar order. The present study demonstrates the simplicity and the versatility of the concept of assembly of n-type electroactive groups mediated by semifluorinated dendrons and assesses the scope and limitations of this supramolecular strategy.

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