π–π Interactions: Influence on Molecular Packing and Solid-State Emission of ESIPT and non-ESIPT Motifs

Vikas S. Padalkar, Daisuke Sakamaki, Kenji Kuwada, Akifumi Horio, Haruka Okamoto, Norimitsu Tohnai, Tomoyuki Akutagawa, Ken Ichi Sakai, Shu Seki

    Research output: Contribution to journalArticlepeer-review

    27 Citations (Scopus)

    Abstract

    Novel, triphenylamino benzothiazole-based excited-state intramolecular proton transfer (ESIPT) and non-ESIPT fluorophores were prepared by Suzuki coupling reactions. Their photophysical properties in solution, aqueous suspension, and in the solid state were systematically investigated. High fluorescence quantum efficiencies (Φsol≈95 %; Φsolid≈88 %), moderate Stokes shifts (≈8000 cm−1), microenvironment-sensitive and molecular-framework-dependent emission are the striking features of the protocol described here. Solid-state emission was modulated and interpreted as a crossover effect of π–π interactions using single-crystal X-ray analyses. The nonplanar/twisted framework of the system helps to avoid noncovalent interactions, facilitating the suppression of fluorescence quenching in the solid state with high quantum efficiency over 88 %.

    Original languageEnglish
    Pages (from-to)938-945
    Number of pages8
    JournalAsian Journal of Organic Chemistry
    Volume5
    Issue number7
    DOIs
    Publication statusPublished - 2016 Jul 1

    Keywords

    • aggregation-induced emission
    • excited-state intramolecular proton transfer
    • fluorescence
    • molecular packing
    • photophysics

    ASJC Scopus subject areas

    • Organic Chemistry

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