Characterization of new rubrene analogues with heteroaryl substituents

Masashi Mamada, Hiroshi Katagiri, Tomo Sakanoue, Shizuo Tokito

    Research output: Contribution to journalArticle

    13 Citations (Scopus)

    Abstract

    New rubrene analogues, which are heteroaryl-tetrasubstituted tetracenes, have been developed using a simplified synthesis approach. Their stabilities in solution were improved compared to those of rubrene. The correlation among the molecular structures, crystal structures, and charge transport properties has been investigated and compared with rubrene and various rubrene analogues. Although twisted structures of a tetracene backbone have often been found in single crystal analyses, the planarity might be related to intermolecular interactions rather than the electron donating/withdrawing properties of the heteroaryl side groups. The packing motifs in thiophene-substituted derivatives did not include π-stacking of tetracene cores, which differ from the well-known structure of rubrene. However, furan-substituted derivatives can be crystallized in the π-stacking manner. These differences in the packing structure affect hole transport properties.

    Original languageEnglish
    Pages (from-to)442-448
    Number of pages7
    JournalCrystal Growth and Design
    Volume15
    Issue number1
    DOIs
    Publication statusPublished - 2015 Jan 7

    Fingerprint

    Transport properties
    transport properties
    analogs
    Derivatives
    furans
    Thiophene
    thiophenes
    Molecular structure
    Charge transfer
    Naphthacenes
    molecular structure
    Crystal structure
    Single crystals
    crystal structure
    Electrons
    single crystals
    synthesis
    Thiophenes
    electrons
    interactions

    ASJC Scopus subject areas

    • Chemistry(all)
    • Materials Science(all)
    • Condensed Matter Physics

    Cite this

    Characterization of new rubrene analogues with heteroaryl substituents. / Mamada, Masashi; Katagiri, Hiroshi; Sakanoue, Tomo; Tokito, Shizuo.

    In: Crystal Growth and Design, Vol. 15, No. 1, 07.01.2015, p. 442-448.

    Research output: Contribution to journalArticle

    Mamada, M, Katagiri, H, Sakanoue, T & Tokito, S 2015, 'Characterization of new rubrene analogues with heteroaryl substituents', Crystal Growth and Design, vol. 15, no. 1, pp. 442-448. https://doi.org/10.1021/cg501519a
    Mamada, Masashi ; Katagiri, Hiroshi ; Sakanoue, Tomo ; Tokito, Shizuo. / Characterization of new rubrene analogues with heteroaryl substituents. In: Crystal Growth and Design. 2015 ; Vol. 15, No. 1. pp. 442-448.
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