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Oligo(p-phenylene ethynylene)–BODIPY Derivatives: Synthesis, Energy Transfer, and Quantum-Chemical Calculations

Authors

  • Dr. Shouchun Yin ,

    1. Department of Chemistry, Katholieke Universiteit Leuven, Celestijnenlaan 200f - bus 02404, 3001 Leuven (Belgium), Fax: (+32) 16-327990
    2. College of Material Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou 310036 (P. R. China)
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  • Dr. Volker Leen,

    1. Department of Chemistry, Katholieke Universiteit Leuven, Celestijnenlaan 200f - bus 02404, 3001 Leuven (Belgium), Fax: (+32) 16-327990
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  • Carine Jackers ,

    1. Department of Chemistry, Katholieke Universiteit Leuven, Celestijnenlaan 200f - bus 02404, 3001 Leuven (Belgium), Fax: (+32) 16-327990
    2. Institute for Nanoscale Physics and Chemistry (INPAC), Department of Chemistry, Katholieke Universiteit Leuven, Celestijnenlaan 200f - bus 02404, 3001 Leuven (Belgium)
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  • Prof. David Beljonne,

    Corresponding author
    1. Laboratory for Chemistry of Novel Materials, Université de Mons, Place du Parc 20, 7000 Mons (Belgium)
    • Laboratory for Chemistry of Novel Materials, Université de Mons, Place du Parc 20, 7000 Mons (Belgium)
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  • Dr. Bernard Van Averbeke,

    1. Laboratory for Chemistry of Novel Materials, Université de Mons, Place du Parc 20, 7000 Mons (Belgium)
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  • Prof. Mark Van der Auweraer ,

    1. Department of Chemistry, Katholieke Universiteit Leuven, Celestijnenlaan 200f - bus 02404, 3001 Leuven (Belgium), Fax: (+32) 16-327990
    2. Institute for Nanoscale Physics and Chemistry (INPAC), Department of Chemistry, Katholieke Universiteit Leuven, Celestijnenlaan 200f - bus 02404, 3001 Leuven (Belgium)
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  • Prof. Noël Boens,

    1. Department of Chemistry, Katholieke Universiteit Leuven, Celestijnenlaan 200f - bus 02404, 3001 Leuven (Belgium), Fax: (+32) 16-327990
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  • Prof. Wim Dehaen

    Corresponding author
    1. Department of Chemistry, Katholieke Universiteit Leuven, Celestijnenlaan 200f - bus 02404, 3001 Leuven (Belgium), Fax: (+32) 16-327990
    • Department of Chemistry, Katholieke Universiteit Leuven, Celestijnenlaan 200f - bus 02404, 3001 Leuven (Belgium), Fax: (+32) 16-327990
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Abstract

The synthesis and energy-transfer properties of a series of oligo(p-phenylene ethynylene)–BODIPY (OPEB) cassettes are reported. A series of oligo(p-phenylene ethynylene)s (OPEs) with different conjugated chain lengths as energy donor subunit in the energy-transfer system were capped at both ends with BODIPY chromophores as energy-acceptor subunits. The effect of the conjugated chain of OPEs on energy transfer in the OPEB cassettes was investigated by UV/Vis and fluorescence spectroscopy and modeling. With increasing number n of phenyl acetylene units (n=1–7), the absorption and emission maxima of OPEn are bathochromically shifted. In the OPEBn analogues, the absorption maximum assigned to the BODIPY moieties is independent of the length of the OPE spacer. However, the relative absorption intensity of the BODIPY band decreases when the number of phenyl acetylene units is increased. The emission spectra of OPEBn are dominated by a band peaking at 613 nm, corresponding to emission of the BODIPY moieties, regardless of whether excitation is at 420 or 550 nm. Furthermore, a very small band is observed with a maximum between 450 and 500 nm, and its intensity relative to that of the BODIPY emission increases with increasing n, that is, the excited state of OPE subunits is efficiently quenched in OPEBn by energy transfer to the BODIPY moieties. Energy transfer (ET) from OPEn to BODIPY in OPEBn is very efficient (all ΦET values are greater than 98 %) and only slightly decreases with increasing length of the OPE units. These results are supported by theoretical studies that show very high energy transfer efficiency (ΦET>75 %) from the OPE spacer to the BODIPY end-groups for chains with up to 15–20 units.

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