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  • Title: 8-Alkoxy- and 8-aryloxy-BODIPYs: straightforward fluorescent tagging of alcohols and phenols.
    Author: Flores-Rizo JO, Esnal I, Osorio-Martínez CA, Gómez-Durán CF, Bañuelos J, López Arbeloa I, Pannell KH, Metta-Magaña AJ, Peña-Cabrera E.
    Journal: J Org Chem; 2013 Jun 21; 78(12):5867-77. PubMed ID: 23721096.
    Abstract:
    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(N)Ar-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.
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