Bis(10-methylacridinium)s as a versatile platform for redox-active functionalized dyes and novel structures

Takanori Suzuki, Takashi Takeda, Eisuke Ohta, Kazuhisa Wada, Ryo Katoono, Hidetoshi Kawai, Kenshu Fujiwara

    Research output: Contribution to journalArticlepeer-review

    19 Citations (Scopus)

    Abstract

    10-Methylacridinium is a stable aromatic cation exhibiting yellow-orange color and strong green fluorescence (FL), and can be used as a versatile building block in constructing a wide variety of novel π-electron systems. The dications with the two chromophores connected by a proper π spacer undergo reversible "dyrex" (dynamic redox) behavior, and C-C bond formation/ cleavage is accompanied by their redox reactions. The prototype is biphenyl-2,2?-diylbis(10- methylacridinium), which exhibits electrochromic response with ON/OFF switching of FL during the reversible interconversion with the di(spiroacridan)-type electron donor. Slight structural alteration under the concept of "MFMS" (maximum function on the minimum skeleton) endowed the dyrex system with metal-binding or chiroptical properties, which could be modified by the redox reactions. Some of the di(spiroacridan) derivatives generated from bis(10- methylacridinium)s have extreme structural parameters, such as the greatest C-C bond length ever reported.

    Original languageEnglish
    Pages (from-to)280-294
    Number of pages15
    JournalChemical Record
    Volume15
    Issue number1
    DOIs
    Publication statusPublished - 2015 Feb

    Keywords

    • Cations
    • Heterocycles
    • Redox chemistry
    • Steric hindrance
    • Strained molecules

    ASJC Scopus subject areas

    • Chemistry(all)
    • Biochemistry
    • Chemical Engineering(all)
    • Materials Chemistry

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