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, Brendon William Lovett, J.J.L. Morton, H.L. Anderson

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26 Citations (Scopus)
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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 C, as a better electron-acceptor than triptycenenaphthoquinone (TNQ). The C-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.
Original languageEnglish
Pages (from-to)6468-6481
Number of pages14
JournalChemical Science
Volume6
Issue number11
Early online date31 Jul 2015
DOIs
Publication statusPublished - 1 Nov 2015

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