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Download Hi-Res ImageDownload to MS-PowerPointCite This:J. Am. Chem. Soc. 2017, 139, 48, 17474-17483
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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
*[email protected]
*[email protected]
*[email protected]
*[email protected]
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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