Fluorogenic probes for chemical transformations: 9-anthracene derivatives for monitoring reaction progress by an increase in fluorescence

TETRAHEDRON LETTERS

卷:54

Article

Mase, Nobuyuki^1,2,3  Takabe, Kunihiko³  Tanaka, Fujie^4,5 

[1] Shizuoka Univ, Dept Appl Chem & Biochem Engn, Fac Engn, Hamamatsu, Shizuoka 4328561, Japan

[2] Shizuoka Univ, Green Energy Res Div, Res Inst Green Sci & Technol, Hamamatsu, Shizuoka 4328561, Japan

[3] Shizuoka Univ, Dept Mol Sci, Fac Engn, Hamamatsu, Shizuoka 4328561, Japan

[4] Grad Univ, Okinawa Inst Sci & Technol, Okinawa 9040495, Japan

[5] Grad Univ, Okinawa Inst Sci & Technol, Kyoto 6020841, Japan

关键词: Fluorogenic probe;    Fluorescent molecules;    High-throughput screening;    Carbon-carbon bond formation;    Reaction sensor;   

DOI  :  10.1016/j.tetlet.2013.06.010

来源: Elsevier

【 摘 要 】

The development of fluorogenic probes for chemical transformations bearing anthracene as a fluorescent core moiety is reported. Fluorogenic probes were designed by linking anthracene with functional groups used for reactions of interest. Each fluorogenic probe, possessing a reaction group such as aldehyde, alpha,beta-unsaturated ketone, or imine at the 9-position of the anthracene, showed no or very low fluorescence. Reaction products of the probes, including aldol and addition products, were highly fluorescent. The products showed more than 1000-fold higher fluorescence than did the fluorogenic probes under the same conditions. The utility of the fluorogenic probes was demonstrated in monitoring the progress of a catalyzed aldol reaction. (C) 2013 Elsevier Ltd. All rights reserved.

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