New fluorimetric alkali and alkaline earth metal cation sensors based on noncyclic crown ethers by means of intramolecular excimer formation of pyrene

Yoshio Suzuki, Tatsuya Morozumi, Hiroshi Nakamura, Masatsugu Shimomura, Takashi Hayashita, Richard A. Bartsh

    Research output: Contribution to journalArticle

    105 Citations (Scopus)

    Abstract

    New fluorescent reagents, 2,2′-[oxybis(3-oxapentamethyleneoxy)]-bis[N-(1-pyrenylmethyl)benzamide)] (4) and its analogues (2, 3, and 5) which have two pyrenes at the both terminals of polyoxyethylene compounds, were synthesized, and their complexation behavior with alkaline earth cations was investigated by fluorescence spectrometry, fluorescence lifetimes, and 1H NMR spectrometry. These reagents (3-5) showed strong intramolecular excimer emissions around at 480 nm in the fluorescence spectra. On the complexation with alkaline earth metal cations, the increase of monomer emission around at 400 nm accompanied by the disappearance of intramolecular excimer emission of free reagents was observed. These reagents formed a 1:1 complex, and the order of complex formation constants was Ca2+ ≅ Sr2+ > Ba2+ > Mg2+ > Li+ for all reagents. 1H NMR spectra of these complexes with alkaline earth cations suggested the helical structures of the complexes. Fluorescence spectral changes at the formation of complexes depended on the chain length of the oxyethylene moiety and metal cations. In all cases, the formation of helical structures at the complexation was supported by the 1H NMR spectra.

    Original languageEnglish
    Pages (from-to)7910-7917
    Number of pages8
    JournalJournal of Physical Chemistry B
    Volume102
    Issue number40
    Publication statusPublished - 1998 Oct 1

    ASJC Scopus subject areas

    • Physical and Theoretical Chemistry
    • Surfaces, Coatings and Films
    • Materials Chemistry

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