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Issue 11, 2015
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Synthesis and investigation of donor–porphyrin–acceptor triads with long-lived photo-induced charge-separate states

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Abstract

Two donor–porphyrin–acceptor triads have been synthesized using a versatile Suzuki-coupling route. This synthetic strategy allows the powerful donor tetraalkylphenylenediamine (TAPD) to be introduced into tetraarylporphyrin-based triads without protection. The thermodynamics and kinetics of electron transfer in the new triads are compared with a previously reported octaalkyldiphenyl-porphyrin triad exhibiting a long-lived spin-polarized charge separate state (CSS), from theoretical and experimental perspectives, in both fluid solution and in a frozen solvent glass. We show that the less favorable oxidation potential of the tetraaryl-porphyrin core can be offset by using C60, as a better electron-acceptor than triptycenenaphthoquinone (TNQ). The C60–porphyrin–TAPD triad gives a spin-polarized charge-separated state that can be observed by EPR-spectroscopy, with a mean lifetime of 16 ms at 10 K, which is longer than in the previously reported TNQ–porphyrin–TAPD triad, following the predicted trend from calculated charge-recombination rates.

Graphical abstract: Synthesis and investigation of donor–porphyrin–acceptor triads with long-lived photo-induced charge-separate states

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Publication details

The article was received on 20 May 2015, accepted on 30 Jul 2015 and first published on 31 Jul 2015


Article type: Edge Article
DOI: 10.1039/C5SC01830G
Citation: Chem. Sci., 2015,6, 6468-6481
  • Open access: Creative Commons BY license
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    Synthesis and investigation of donor–porphyrin–acceptor triads with long-lived photo-induced charge-separate states

    J. B. Kelber, N. A. Panjwani, D. Wu, R. Gómez-Bombarelli, B. W. Lovett, J. J. L. Morton and H. L. Anderson, Chem. Sci., 2015, 6, 6468
    DOI: 10.1039/C5SC01830G

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