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Mediating Reductive Charge Shift Reactions in Electron Transport Chains

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Department of Chemistry and Pharmacy & Interdisciplinary Center of Molecular Materials (ICMM), Friedrich-Alexander-University Erlangen-Nuremberg, Egerlandstr. 3, 91058 Erlangen, Germany
Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad Complutense de Madrid, Ciudad Universitaria s/n, 28040 Madrid, Spain
§ Departamento de Química Orgánica, Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid, Spain
Imdea-Nanoscience, C/Faraday 9, Campus Cantoblanco, 28049 Madrid, Spain
Faculty of Chemistry & POLYMAT, University of the Basque Country UPV/EHU, Avenida de Tolosa 72, 20018 Donostia-San Sebastian, Spain
# Ikerbasque, Basque Foundation for Science, 48011 Bilbao, Spain
Institute for Advanced Research in Chemical Sciences (IAdChem), Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid, Spain
Department of Chemistry and Pharmacy, Computer Chemistry Centre (CCC), Friedrich-Alexander-University Erlangen-Nuremberg, Nägelsbachstraße 25, 91052 Erlangen, Germany
Cite this: J. Am. Chem. Soc. 2017, 139, 48, 17474–17483
Publication Date (Web):October 13, 2017
https://doi.org/10.1021/jacs.7b08670
Copyright © 2017 American Chemical Society
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Abstract

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We report the synthesis of a full-fledged family of covalent electron donor–acceptor1–acceptor2 conjugates and their charge-transfer characterization by means of advanced photophysical assays. By virtue of variable excited state energies and electron donor strengths, either Zn(II)Porphyrins or Zn(II)Phthalocyanines were linked to different electron-transport chains featuring pairs of electron accepting fullerenes, that is, C60 and C70. In this way, a fine-tuned redox gradient is established to power a unidirectional, long-range charge transport from the excited-state electron donor via a transient C60•– toward C70•–. This strategy helps minimize energy losses in the reductive, short-range charge shift from C60 to C70. At the forefront of our investigations are excited-state dynamics deduced from femtosecond transient absorption spectroscopic measurements and subsequent computational deconvolution of the transient absorption spectra. These provide evidence for cascades of short-range charge-transfer processes, including reductive charge shift reactions between the two electron-accepting fullerenes, and for kinetics that are influenced by the nature and length of the respective spacer. Of key importance is the postulate of a mediating state in the charge-shift reaction at weak electronic couplings. Our results point to an intimate relationship between triplet–triplet energy transfer and charge transfer.

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The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/jacs.7b08670.

  • Detailed synthesis and analyses of the products by NMR, MS, and HPLC, electrochemical results, and additional steady state and time-resolved absorption spectra (PDF)

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