期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 78, 期 12, 页码 5867-5877出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo400417h
关键词
-
资金
- CONACyT [129572]
- Gobierno Vasco [IT339-10, SPE11UN064, SPE12UN140]
- Robert A. Welch Foundation, Houston, TX [0546]
We demonstrate herein that both alcohols and phenols can be tagged with a BODIPY (borondipyrromethene) moiety to yield highly fluorescent products. Thus, 8-(methylthio)-BODIPY (1) undergoes an SNAr-type reaction with a host of alcohols and phenols in the presence of a base and a Cu(I) additive. The BODIPY dyes bearing alkoxy or nonfunctionalized phenoxy moieties are characterized by a highly efficient fluorescence emission, regardless of the media, in the blue-green part of the visible region. Complementary to this, the presence of electron-donor groups at the aryl ring leads to an intramolecular charge-transfer process, which quenches the fluorescence mainly in polar media. In addition to simple alcohols and phenols, four natural products (eugenol, menthol, cholesterol, and estrone) were labeled in a simple fashion. X-ray structures of the cholesterol and estrone derivatives are discussed. In fact, the BODIPY bearing cholesterol stands out as a bright fluorescence biological marker.
作者
我是这篇论文的作者
点击您的名字以认领此论文并将其添加到您的个人资料中。
推荐
暂无数据