title: 8-Alkoxy- and 8-aryloxy-BODIPYs: straightforward fluorescent tagging of alcohols and phenols.
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.
authors.affiliation: Departamento de Quı́mica, Universidad de Guanajuato, Col. Noria Alta S/N, Guanajuato, Gto. 36050, Mexico.
authors.forename: Juan O
authors.initials: JO
authors.lastname: Flores-Rizo
authors.forename: Ixone
authors.initials: I
authors.lastname: Esnal
authors.forename: Carlos A
authors.initials: CA
authors.lastname: Osorio-Martínez
authors.forename: César F A
authors.initials: CF
authors.lastname: Gómez-Durán
authors.forename: Jorge
authors.initials: J
authors.lastname: Bañuelos
authors.forename: Iñigo
authors.initials: I
authors.lastname: López Arbeloa
authors.forename: Keith H
authors.initials: KH
authors.lastname: Pannell
authors.forename: Alejandro J
authors.initials: AJ
authors.lastname: Metta-Magaña
authors.forename: Eduardo
authors.initials: E
authors.lastname: Peña-Cabrera
mesh_terms: D000438:Alcohols / Q000737:chemistry*; D001896:Boron Compounds / Q000737:chemistry*; D002784:Cholesterol / Q000737:chemistry; D018360:Crystallography, X-Ray; D004970:Estrone / Q000737:chemistry; D005054:Eugenol / Q000737:chemistry; D005456:Fluorescent Dyes / Q000737:chemistry*; D008610:Menthol / Q000737:chemistry; D010636:Phenols / Q000737:chemistry*; D013050:Spectrometry, Fluorescence; D013194:Staining and Labeling / Q000379:methods*; D055672:Static Electricity
chemical_list: C095489:4,4-difluoro-4-bora-3a,4a-diaza-s-indacene; D000438:Alcohols; D001896:Boron Compounds; D005456:Fluorescent Dyes; D010636:Phenols; C059688:alkoxyl radical; D008610:Menthol; D004970:Estrone; D005054:Eugenol; D002784:Cholesterol