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    Rubrene: The interplay between intramolecular and intermolecular interactions determines the planarization of its tetracene core in the solid state

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    Type
    Article
    Authors
    Sutton, Christopher
    Marshall, Michael S.
    Sherrill, C. David
    Risko, Chad
    Bredas, Jean-Luc cc
    KAUST Department
    KAUST Solar Center (KSC)
    Laboratory for Computational and Theoretical Chemistry of Advanced Materials
    Material Science and Engineering Program
    Physical Science and Engineering (PSE) Division
    Date
    2015-07-02
    Online Publication Date
    2015-07-02
    Print Publication Date
    2015-07-15
    Permanent link to this record
    http://hdl.handle.net/10754/558300
    
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    Abstract
    Rubrene is one of the most studied molecular semiconductors; its chemical structure consists of a tetracene backbone with four phenyl rings appended to the two central fused rings. Derivatization of these phenyl rings can lead to two very different solid-state molecular conformations and packings: One in which the tetracene core is planar and there exists substantive overlap among neighboring π-conjugated backbones; and another where the tetracene core is twisted and the overlap of neighboring π-conjugated backbones is completely disrupted. State-of-the-art electronic-structure calculations show for all isolated rubrene derivatives that the twisted conformation is more favorable (by -1.7 to -4.1 kcal mol-1), which is a consequence of energetically unfavorable exchange-repulsion interactions among the phenyl side groups. Calculations based on available crystallographic structures reveal that planar conformations of the tetracene core in the solid state result from intermolecular interactions that can be tuned through well-chosen functionalization of the phenyl side groups, and lead to improved intermolecular electronic couplings. Understanding the interplay of these intramolecular and intermolecular interactions provides insight into how to chemically modify rubrene and similar molecular semiconductors to improve the intrinsic materials electronic properties.
    Citation
    Rubrene: The interplay between intramolecular and intermolecular interactions determines the planarization of its tetracene core in the solid state 2015:150615105527002 Journal of the American Chemical Society
    Publisher
    American Chemical Society (ACS)
    Journal
    Journal of the American Chemical Society
    DOI
    10.1021/jacs.5b04066
    PubMed ID
    26075966
    Additional Links
    http://pubs.acs.org/doi/abs/10.1021/jacs.5b04066
    ae974a485f413a2113503eed53cd6c53
    10.1021/jacs.5b04066
    Scopus Count
    Collections
    Articles; Physical Science and Engineering (PSE) Division; Material Science and Engineering Program; KAUST Solar Center (KSC)

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