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    Control of polymer-packing orientation in thin films through synthetic tailoring of backbone coplanarity

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    Type
    Article
    Authors
    Chen, Mark S.
    Niskala, Jeremy R.
    Unruh, David A.
    Chu, Crystal K.
    Lee, Olivia P.
    Frechet, Jean cc
    KAUST Department
    Chemical Science Program
    Office of the VP
    Physical Science and Engineering (PSE) Division
    KAUST Grant Number
    KUS-C1-015-21
    Date
    2013-10-08
    Online Publication Date
    2013-10-08
    Print Publication Date
    2013-10-22
    Permanent link to this record
    http://hdl.handle.net/10754/563046
    
    Metadata
    Show full item record
    Abstract
    Controlling solid-state order of π-conjugated polymers through macromolecular design is essential for achieving high electronic device performance; yet, it remains a challenge, especially with respect to polymer-packing orientation. Our work investigates the influence of backbone coplanarity on a polymer's preference to pack face-on or edge-on relative to the substrate. Isoindigo-based polymers were synthesized with increasing planarity by systematically substituting thiophenes for phenyl rings in the acceptor comonomer. This increasing backbone coplanarity, supported by density functional theory (DFT) calculations of representative trimers, leads to the narrowing of polymer band gaps as characterized by ultraviolet-visible-near infrared (UV-vis-NIR) spectroscopy and cyclic voltammetry. Among the polymers studied, regiosymmetric II and TII polymers exhibited the highest hole mobilities in organic field-effect transistors (OFETs), while in organic photovoltaics (OPVs), TBII polymers that display intermediate levels of planarity provided the highest power conversion efficiencies. Upon thin-film analysis by atomic force microscropy (AFM) and grazing-incidence X-ray diffraction (GIXD), we discovered that polymer-packing orientation could be controlled by tuning polymer planarity and solubility. Highly soluble, planar polymers favor face-on orientation in thin films while the less soluble, nonplanar polymers favor an edge-on orientation. This study advances our fundamental understanding of how polymer structure influences nanostructural order and reveals a new synthetic strategy for the design of semiconducting materials with rationally engineered solid-state properties. © 2013 American Chemical Society.
    Citation
    Chen, M. S., Niskala, J. R., Unruh, D. A., Chu, C. K., Lee, O. P., & Fréchet, J. M. J. (2013). Control of Polymer-Packing Orientation in Thin Films through Synthetic Tailoring of Backbone Coplanarity. Chemistry of Materials, 25(20), 4088–4096. doi:10.1021/cm402489a
    Sponsors
    This work was supported in part by King Abdullah University of Science and Technology (KAUST) through the Center for Advanced Molecular Photovoltaics (CAMP) under Award No. KUS-C1-015-21, and the Frechet "various gifts" fund for the support of research in new materials. Portions of this research were carried out at the Stanford Synchrotron Radiation Lightsource user facility, operated on behalf of the U.S. Department of Energy, Office of Basic Energy Sciences. M.S.C. thanks the Camille and Henry Dreyfus Postdoctoral Program in Environmental Chemistry for a fellowship; the assistance of Jessica C. Moreton is acknowledged with thanks.
    Publisher
    American Chemical Society (ACS)
    Journal
    Chemistry of Materials
    DOI
    10.1021/cm402489a
    ae974a485f413a2113503eed53cd6c53
    10.1021/cm402489a
    Scopus Count
    Collections
    Articles; Physical Science and Engineering (PSE) Division; Chemical Science Program

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