8-Alkoxy- and 8-aryloxy-BODIPYs: straightforward fluorescent tagging of alcohols and phenols.
J Org Chem
; 78(12): 5867-77, 2013 Jun 21.
Article
em En
| MEDLINE
| ID: mdl-23721096
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.
Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Fenóis
/
Coloração e Rotulagem
/
Compostos de Boro
/
Álcoois
/
Corantes Fluorescentes
Idioma:
En
Revista:
J Org Chem
Ano de publicação:
2013
Tipo de documento:
Article
País de afiliação:
México
País de publicação:
Estados Unidos