8-Alkoxy- and 8-Aryloxy-BODIPYs: Straightforward Fluorescent Tagging of Alcohols and Phenols

详细信息    查看全文

• 作者：Juan O. Flores-Rizo ; Ixone Esnal ; Carlos A. Osorio-Martı ; ́ ; nez ; C茅sar F. A. G贸mez-Dur谩n ; Jorge Ba帽uelos ; I帽igo L贸pez Arbeloa ; Keith H. Pannell ; Alejandro J. Metta-Maga帽a ; Eduardo Pe帽a-Cabrera
• 刊名：The Journal of Organic Chemistry
• 出版年：2013
• 出版时间：June 21, 2013
• 年：2013
• 卷：78
• 期：12
• 页码：5867-5877
• 全文大小：599K
• 年卷期：v.78,no.12(June 21, 2013)
• ISSN：1520-6904

文摘

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 S_NAr-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.