Synthesis and Characterization of Zinc Sensors Based on a Monosubstituted Fluorescein Platform

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• 作者：Elizabeth M. Nolan ; Shawn C. Burdette ; Jessica H. Harvey ; Scott A. Hilderbrand ; and Stephen J. Lippard
• 刊名：Inorganic Chemistry
• 出版年：2004
• 出版时间：April 19, 2004
• 年：2004
• 卷：43
• 期：8
• 页码：2624 - 2635
• 全文大小：189K
• 年卷期：v.43,no.8(April 19, 2004)
• ISSN：1520-510X

文摘

The synthesis of a new fluorescein carboxaldehyde asymmetrically substituted on the xanthene (top) ring is reported.This molecule is a key precursor for two of three monofunctionally derivatized fluorescein-based Zn(II) sensorspresented in this work. Detailed preparative routes to, and photophysical characterization of, these sensors aredescribed. The sensors are based on the previously reported ZP4 motif (Burdette, S. C.; Frederickson, C. J.; Bu,W.; Lippard, S. J. J. Am. Chem. Soc. 2003, 125, 1778-1787) and incorporate a di(2-picolyl)amine-containinganiline-derivatized ligand framework. By varying the nature of the substituent (X) para to the aniline nitrogen atom,which is responsible for PET quenching of the unbound ZP dye, we investigated the extent to which such electronictuning might improve the fluorescent properties of asymmetrical ZP sensors. Although a comparison of probes withX = H, F, Cl, OMe reveals that the photophysical behavior of these dyes is not readily predictable, our methodologyillustrates the ease with which aniline-based ligands may be linked to fluorescein dyes.