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Synthesis of Zwitterionic Water-Soluble Oligofluorenes with Good Light-Harvesting Ability

Authors

  • Chengfen Xing,

    1. Beijing National Laboratory for Molecular Science, Key Laboratory of Organic Solids Institute of Chemistry, Chinese Academy of Sciences Beijing, 100190 (P.R. China)
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  • Libing Liu,

    1. Beijing National Laboratory for Molecular Science, Key Laboratory of Organic Solids Institute of Chemistry, Chinese Academy of Sciences Beijing, 100190 (P.R. China)
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  • Zhiqiang Shi,

    Corresponding author
    1. Department of Chemistry, Shandong Normal University Jinan 250014, Shandong Province (P.R. China)
    • Department of Chemistry, Shandong Normal University Jinan 250014, Shandong Province (P.R. China).
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  • Yuliang Li,

    1. Beijing National Laboratory for Molecular Science, Key Laboratory of Organic Solids Institute of Chemistry, Chinese Academy of Sciences Beijing, 100190 (P.R. China)
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  • Shu Wang

    Corresponding author
    1. Beijing National Laboratory for Molecular Science, Key Laboratory of Organic Solids Institute of Chemistry, Chinese Academy of Sciences Beijing, 100190 (P.R. China)
    • Beijing National Laboratory for Molecular Science, Key Laboratory of Organic Solids Institute of Chemistry, Chinese Academy of Sciences Beijing, 100190 (P.R. China).
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Abstract

A new water-soluble zwitterionic oligofluorene bearing carboxylic acid and quaternary ammonium as pendant groups (OF-1) is synthesized and characterized. It forms aggregates by intermolecular electrostatic interactions and exhibits similar light-harvesting ability as that of conjugated polymers. Efficient fluorescence resonance energy transfer (FRET) occurs from OF-1 to double-stranded DNA tagged with fluorescein (dsDNA-F1). A photoresponsive oligofluorene (OF-3) is also synthesized by protecting OF-1 with 1-(2-nitrophenyl)ethanol. Photolysis of OF-3 can produce OF-1 to result in a fluorescence “turn-on” response, thus the FRET from OF-3 to dsDNA-Fl can be turned on by light irradiation. OF-3 offers the potential for remote DNA sensing.

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