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Issue 19, 2009
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Bisquinoline-based fluorescent zinc sensors

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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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Supplementary files

Article information

20 Nov 2008
25 Feb 2009
First published
27 Mar 2009

Dalton Trans., 2009, 3800-3806
Article type

Bisquinoline-based fluorescent zinc sensors

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

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