Systematic control of the excited-state dynamics and carrier-transport properties of functionalized benzo[ghi]perylene and coronene derivatives

Sunao Hirayama, Hayato Sakai, Yasuyuki Araki, Minako Tanaka, Masaki Imakawa, Takehiko Wada, Taishi Takenobu, Taku Hasobe

    Research output: Contribution to journalArticle

    27 Citations (Scopus)

    Abstract

    A series of benzo[ghi]perylene (Bp) and coronene (Cor) derivatives substituted with electron-withdrawing methoxycarbonyl (COOMe) or electron-donating methoxyl (MeO) groups was synthesized. The electrochemical, spectroscopic, and photophysical properties of these compounds were investigated by cyclic voltammetry, steady-state and time-resolved spectroscopy, and quantum-yield measurements. Introduction of suitable substituents onto the aromatic rings enabled control of electrochemical and spectroscopic behavior. Examination of excited-state dynamics revealed that fluorescence quantum yields increased with increasing number of COOMe groups in both Bp and Cor derivatives, consistent with the findings of DFT calculations. Single-crystal analysis allowed the performance of field-effect transistors containing single crystals of the derivatives to be rationalized. Crown decoration: A series of benzo[ghi]perylene and coronene derivatives decorated with different numbers of electron-donating or electron-withdrawing substituents was synthesized in order to control their fluorescence quantum yields and carrier-transport properties (see figure).

    Original languageEnglish
    Pages (from-to)9081-9093
    Number of pages13
    JournalChemistry - A European Journal
    Volume20
    Issue number29
    DOIs
    Publication statusPublished - 2014 Jul 14

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    Keywords

    • device fabrication
    • electrochemistry
    • fluorescence
    • polycycles
    • solid-state structures

    ASJC Scopus subject areas

    • Chemistry(all)

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