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Issue 19, 2009
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Bisquinoline-based fluorescent zinc sensors

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Abstract

Several bisquinoline derivatives, N,N′-bis(2-quinolylmethyl)-N,N′-dialkylethylnediamines (alkyl = methyl, ethyl, isopropyl and t-butyl), have been synthesized and their fluorescent responses toward zinc ion were investigated. These compounds exhibit zinc ion-induced fluorescence and their intensities decrease as the alkyl groups become larger. The t-butyl derivative (BQDtBEN) exhibited negligible fluorescence even in the presence of zinc ion. The fluorescence intensity of the zinc complex of the bisquinoline derivative (BQDMEN) is higher than that of TQEN (N,N,N′,N′-tetrakis(2-quinolylmethyl)ethylenediamine), indicating that the TQEN-Zn complex has an intramolecular quenching mechanism due to the energy transfer among four quinoline rings and the remaining photoinduced electron transfer (PET) mechanism. Introduction of methoxy substituents into the quinoline ring shifted the excitation and emission wavelengths towards a lower-energy direction and increased the fluorescence intensity, which allows N,N′-bis(6-methoxy-2-quinolylmethyl)-N,N′-dimethylethylenediamine (6-MeOBQDMEN) to be used for cellular fluorescent microscopic analysis (λex = 331 nm, λem = 406 nm and ϕ = 0.28 for 6-MeOBQDMEN-Zn complex)

Graphical abstract: Bisquinoline-based fluorescent zinc sensors

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Publication details

The article was received on 20 Nov 2008, accepted on 25 Feb 2009 and first published on 27 Mar 2009


Article type: Paper
DOI: 10.1039/B820763A
Citation: Dalton Trans., 2009,0, 3800-3806

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    Bisquinoline-based fluorescent zinc sensors

    Y. Mikata, A. Yamashita, A. Kawamura, H. Konno, Y. Miyamoto and S. Tamotsu, Dalton Trans., 2009, 0, 3800
    DOI: 10.1039/B820763A

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