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    Influence of Molecular Aggregation on Electron Transfer at the Perylene Diimide/Indium-Tin Oxide Interface

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    Author
    Zheng, Yilong
    Jradi, Fadi M.
    Parker, Timothy C.
    Barlow, Stephen
    Marder, Seth R.
    Saavedra, S. Scott
    Affiliation
    Department of Chemistry & Biochemistry, University of Arizona
    Issue Date
    2016-12-14
    Keywords
    perylene diimide
    phosphonic acid
    electrochemistry
    electron transfer
    indium-tin oxide
    organic electronics
    electron self-exchange
    potential-modulated ATR spectroscopy
    
    Metadata
    Show full item record
    Publisher
    AMER CHEMICAL SOC
    Citation
    Influence of Molecular Aggregation on Electron Transfer at the Perylene Diimide/Indium-Tin Oxide Interface 2016, 8 (49):34089 ACS Applied Materials & Interfaces
    Journal
    ACS Applied Materials & Interfaces
    Rights
    Copyright © 2016, American Chemical Society.
    Collection Information
    This item from the UA Faculty Publications collection is made available by the University of Arizona with support from the University of Arizona Libraries. If you have questions, please contact us at repository@u.library.arizona.edu.
    Abstract
    Chemisorption of an organic monolayer to tune the surface properties of a transparent conductive oxide (TCO) electrode can improve the performance of organic electronic devices that rely on efficient charge transfer between an organic active layer and a TCO contact. Here, a series of perylene diimides (PDIs) was synthesized and used to study relationships between monolayer structure/properties and electron transfer kinetics at PDI-modified indium-tin oxide (ITO) electrodes. In these PDI molecules, one of the imide substituents is a benzene ring bearing a phosphonic acid (PA) and the other is a bulky aryl group that is twisted out of the plane of the PDI core. The size of the bulky aryl group and the substitution of the benzene ring bearing the PA were both varied, which altered the extent of aggregation when these molecules were absorbed as monolayer films (MLs) on ITO, as revealed by both attenuated total reflectance (ATR) and total internal reflection fluorescence spectra. Polarized ATR measurements indicate that, in these MLs, the long axis of the PDI core is tilted at an angle of 33-42 degrees relative to the surface normal; the tilt angle increased as the degree of bulky substitution increased. Rate constants for electron transfer (k(s,opt)) between these redox-active modifiers and ITO were determined by potential-modulated ATR spectroscopy. As the degree of PDI aggregation was reduced, k(s,opt) declined, which is attributed to a reduction in the lateral electron self-exchange rate between adsorbed PDI molecules, as well as the heterogeneous conductivity of the ITO electrode surface. Photoelectrochemical measurements using a dissolved aluminum phthalocyanine as an electron donor showed that ITO modified with any of these PDIs is a more effective electron-collecting electrode than bare ITO.
    Note
    November 15, 2016; 12 month embargo.
    ISSN
    1944-8244
    1944-8252
    DOI
    10.1021/acsami.6b10731
    Version
    Final accepted manuscript
    Sponsors
    Center for Interface Science: Solar-Electric Materials (CIS:SEM), an Energy Frontier Research Center - U.S. Department of Energy, Office of Science, Office of Basic Energy Sciences [DE-SC0001084]; National Science Foundation [DMR-1506504]; Department of the Navy, Office of Naval Research [N00014-14-1-0580/N00014-16-1-2520]
    Additional Links
    http://pubs.acs.org/doi/abs/10.1021/acsami.6b10731
    ae974a485f413a2113503eed53cd6c53
    10.1021/acsami.6b10731
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