瓜环 染料.pdf

ORGANIC LETTERS Design of a Fluorescent Dye for 2008 Vol. 10, No. 18 Indicator Displacement from 4089-4092 Cucurbiturils: A Macrocycle-Responsive Fluorescent Switch Operating through a pKa Shift Antonia Praetorius, David M. Bailey, Thomas Schwarzlose, and Werner M. Nau* School of Engineering and Science, Jacobs UniVersity Bremen, Campus Ring 1, D-28759 Bremen, Germany w.nau@jacobs-uniVersity.de Received July 16, 2008 ABSTRACT The derivatization of 3-amino-9-ethylcarbazole with a diamino-alkyl anchor affords a fluorescent dye suitable for indicator displacement from cucurbituril macrocycles. The novel compound 1 shows, due to a complexation-induced pKa shift, a large and predictable dual fluorescence response (100-fold increase at 375 nm and 9-fold decrease at 458 nm) upon supramolecular encapsulation and a strong affinity for cation- receptor macrocycles, in particular cucurbit[6]uril (CB6). A direct application is presented by monitoring the enzymatic activity of lysine decarboxylase. There is presently an increasing interest in the development screening of established commercial dyes. Several dyes with of fluorescent dyes which show a high affinity to macrocycles a favorable combination of affinity and fluorescence response in aqueous media and a concomitant fluorescence change characteris