Analytical Sciences

2-Aminotryptanthrin Derivative with Pyrene as a FRET-based Fluorescent Chemosensor for Al³⁺

Jun KAWAKAMI,* Kenta KIKUCHI,* Kazunori CHIBA,* Noriyuki MATSUSHIMA,* Asako YAMAYA,* Shunji ITO,* Masahiko NAGAKI,* and Haruo KITAHARA**

*Graduate School of Science and Technology, Hirosaki University, 3 Bunkyo-cho, Hirosaki, Aomori 036-8561, Japan
**Department of Natural Science, Faculty of Education, Hirosaki University, 1 Bunkyo-cho, Hirosaki, Aomori 036-8560, Japan

1-(2-Tryptanthrinylaminoacetoxy)-14-(1-pyrenecarboxy)-3,6,9,12-tetraoxatetradecane (T2NH-P5P) was synthesized as a fluorescent chemosensor for Al³⁺. Excited at 325 nm, corresponding to absorption of the pyrene unit of T2NH-P5P, emission at 600 nm from the 2-aminotryptanthrin unit has been observed, indicating that intramolecular fluorescence resonance energy transfer (FRET) occurs in T2NH-P5P. However, when Al³⁺ is added to a solution of T2NH-P5P, the fluorescence of 2-aminotryptanthrin is quenched (FRET-off), whereas that of the pyrene group is revived. Such a FRET "on-off" behavior of T2NH-P5P is not observed for other metal cations (Ca²⁺, Ba²⁺, and Zn²⁺).

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