两种新型氯代荧光素探针染料的合成和表征有机化学.pdfVIP

2009 年第 29 卷 有 机 化 学 Vol. 29, 2009 第 10 期, 1626～1630 Chinese Journal of Organic Chemistry No. 10, 1626～1630 ·研究简报· 两种新型氯代荧光素探针染料的合成和表征 * 徐林飞 白银娟 孙 伟 杨秉勤 史 真 (西北大学化学与材料科学学院 合成与天然功能分子化学教育部重点实验室 西安 710069) 摘要 研究了两种具有空间连接链的新型氯代荧光素探针染料 4,5-二氯-6-(5-羧基戊氨基羰基)荧光素和 2,7-二氯- 6-(5-羧基戊氨基羰基)荧光素的合成. 以氯代间苯二酚和苯三酸酐为起始原料经 7 步反应得到了目标化合物, 产率良好. 测定了目标产物的荧光性能, 结果显示该化合物具有很高的荧光量子产率, 与荧光素母体相比其激发和发射波长明显 向长波方向移动. 所得产物结构经 1H NMR, IR, MALDI-TOF MS 以及元素分析进行了表征. 关键词 荧光素; 荧光探针; 合成 Synthesis and Characterization of Two New Chlorinated Fluorescein Probes Xu, Linfei Bai, Yinjuan* Sun, Wei Yang, Bingqin Shi, Zhen (Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of Ministry of Education, College of Chemistry and Materials Science, Northwest University, Xian 710069 ) Abstract The synthesis of two new chlorinated fluorescein probes with a spacer linker arm, 4,5-dichloro- 6-(5-carboxypentylaminocarbonyl)fluorescein and 2,7-dichloro-6-(5-carboxypentylaminocarbonyl)fluores- cein was studied. The title compounds were prepared using chlororesorcinol and trimellitic anhydride as the starting materials in seven steps, with fine overall yields. The measurement of the fluorescence indicated that the title compounds possessed high quantum yields, and the λex and λem exhibited obvious red-shifts com- 1 pared with fluorescein. The structures of the products were characterized by H NMR, IR, M