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

    25 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

    Fingerprint

    Electron transport properties
    Carrier transport
    Excited states
    Quantum yield
    Derivatives
    Electrons
    Fluorescence
    Single crystals
    Field effect transistors
    Discrete Fourier transforms
    Transport properties
    Cyclic voltammetry
    Spectroscopy
    coronene
    1,12-benzoperylene

    Keywords

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

    ASJC Scopus subject areas

    • Chemistry(all)

    Cite this

    Systematic control of the excited-state dynamics and carrier-transport properties of functionalized benzo[ghi]perylene and coronene derivatives. / Hirayama, Sunao; Sakai, Hayato; Araki, Yasuyuki; Tanaka, Minako; Imakawa, Masaki; Wada, Takehiko; Takenobu, Taishi; Hasobe, Taku.

    In: Chemistry - A European Journal, Vol. 20, No. 29, 14.07.2014, p. 9081-9093.

    Research output: Contribution to journalArticle

    Hirayama, Sunao ; Sakai, Hayato ; Araki, Yasuyuki ; Tanaka, Minako ; Imakawa, Masaki ; Wada, Takehiko ; Takenobu, Taishi ; Hasobe, Taku. / Systematic control of the excited-state dynamics and carrier-transport properties of functionalized benzo[ghi]perylene and coronene derivatives. In: Chemistry - A European Journal. 2014 ; Vol. 20, No. 29. pp. 9081-9093.
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    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).",
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    AU - Tanaka, Minako

    AU - Imakawa, Masaki

    AU - Wada, Takehiko

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