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Issue 17, 2017
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Synthesis, the electronic properties and efficient photoinduced electron transfer of new pyrrolidine[60]fullerene- and isoxazoline[60]fullerene-BODIPY dyads: nitrile oxide cycloaddition under mild conditions using PIFA

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Abstract

Two new BODIPY-C60 dyads, with a pyrrolidine linker (BDP-Pyr) and an isoxazoline linker (BDP-Is) between the two electroactive units, have been synthesized and characterized. Their photophysical and electrochemical properties have been studied in solution by comparing with the reference compounds BDP and [60]fullerene. Both BODIPY-C60 derivatives strongly absorb visible light and by photoexcitation at the BDP unit, these dyads undergo photoinduced electron transfer affording the corresponding charge-separated species. Based on their redox potentials, also the direction of the charge transfer is revealed and a comparison between the dyads with respect to C60 suggested that the new BDP-Is derivative showed a better electron affinity than BDP-Pyr and C60. In addition, the experimental studies were complemented by a theoretical analysis based on semiempirical computations which allowed confirming of the charge transfer mechanism from the BDP core to the C60 cages.

Graphical abstract: Synthesis, the electronic properties and efficient photoinduced electron transfer of new pyrrolidine[60]fullerene- and isoxazoline[60]fullerene-BODIPY dyads: nitrile oxide cycloaddition under mild conditions using PIFA

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Publication details

The article was received on 09 Jun 2017, accepted on 14 Jul 2017 and first published on 17 Jul 2017


Article type: Paper
DOI: 10.1039/C7NJ02057K
Citation: New J. Chem., 2017,41, 9061-9069
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    Synthesis, the electronic properties and efficient photoinduced electron transfer of new pyrrolidine[60]fullerene- and isoxazoline[60]fullerene-BODIPY dyads: nitrile oxide cycloaddition under mild conditions using PIFA

    A. Cabrera-Espinoza, B. Insuasty and A. Ortiz, New J. Chem., 2017, 41, 9061
    DOI: 10.1039/C7NJ02057K

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