2-Aminotryptanthrin Derivative with Pyrene as a FRET-based Fluorescent Chemosensor for Metal Ions

1-(2-tryptanthrinylaminoacetoxy)-14-(1-pyrenecarboxy)-3,6,9,12-tetraoxatetradecane (T2NH-P5P) was synthesized as a fluorescent chemosensor for metal ions. We investigated the metal-ion recognition of T2NH-P5P by separately adding Mg2+, Ca2+, Ba2+, Fe2+, Fe3+, Co2+, Ni2+, Cu2+, Ag+, Zn2+, Cd2+, Hg2+,...

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Bibliographic Details
Published in:Analytical Sciences 2014/10/10, Vol.30(10), pp.949-954
Main Authors: KAWAKAMI, Jun, SOMA, Arisa, KIKUCHI, Kenta, KIKUCHI, Yoh, ITO, Shunji, KITAHARA, Haruo
Format: Article
Language:English
Subjects:
2-aminotryptanthrin
Acetonitrile
Analytical Chemistry
Cadmium
Cations - analysis
Chemistry
Chemoreceptors
Cobalt
Copper
Derivatives
Energy transfer
Fluorescence
fluorescence resonance energy transfer
Fluorescence Resonance Energy Transfer - methods
Fluorescent chemosensor
Fluorescent Dyes - chemistry
Fretting
Mercury (metal)
Metal ions
metal-ion recognition
Metals - analysis
Original Papers
Polyethylene Glycols - chemistry
Pyrene
Pyrenes
Pyrenes - chemistry
Spectrometry, Fluorescence
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Summary:1-(2-tryptanthrinylaminoacetoxy)-14-(1-pyrenecarboxy)-3,6,9,12-tetraoxatetradecane (T2NH-P5P) was synthesized as a fluorescent chemosensor for metal ions. We investigated the metal-ion recognition of T2NH-P5P by separately adding Mg2+, Ca2+, Ba2+, Fe2+, Fe3+, Co2+, Ni2+, Cu2+, Ag+, Zn2+, Cd2+, Hg2+, Al3+, and Pb2+ in an acetonitrile solution. When using excitation at 325 nm, which corresponds to the absorption of the pyrene unit of T2NH-P5P, emission at 600 nm, from the 2-aminotryptanthrin unit, was observed, indicating that intramolecular fluorescence resonance energy transfer (FRET) occurs in T2NH-P5P (FRET-on). However, when Fe2+, Fe3+, Ni2+, Cu2+, Cd2+, Hg2+, and Al3+ were added to an acetonitrile solution of T2NH-P5P, the behavior changed from FRET-on to FRET-off, which means that the fluorescence of 2-aminotryptanthrin was quenched, whereas that of the pyrene group was revived (FRET-off). Especially, this behavior was remarkable for Fe2+, Fe3+, Cu2+, and Hg2+. T2NH-P5P is suitable for use as a fluorescent chemosensor for Fe2+, Fe3+, Cu2+, and Hg2+.
ISSN:0910-6340
1348-2246
DOI:10.2116/analsci.30.949