Synthesis and functionalization of new polyhalogenated {BODIPY} dyes. {Study} of their photophysical properties and singlet oxygen generation

Título

Tipo de publicación

Year of Publication

2012

Autores

Ortiz, MJ, Agarrabeitia, AR, Duran-Sampedro, G, Prieto, JBañuelos, Lopez, TArbeloa, Massad, WA, Montejano, HA, García, NA, Arbeloa, ILopez

Journal

Tetrahedron

Volumen

Pagination

1153–1162

ISSN

0040-4020

Palabras claves

Cross-coupling, Electrophilic substitution reactions, Nucleophilic substitution reactions, Polyiodinated BODIPYs, Singlet oxygen generation

Resumen

A theoretical and experimental study on the iodination of BODIPY dyes with different degrees of substitution has been developed. Polyhalogenated BODIPYs synthesized in this work are the first examples of this type of dyes with more than two halogen atoms in the BODIPY core and they can be selectively functionalized. Surprisingly, the position in which halogen is attached has a marked effect in the photophysical properties and modulates the fluorescence capacity of the resulting BODIPY. These iodinated BODIPYs are efficient singlet oxygen generators.

URL

http://www.sciencedirect.com/science/article/pii/S0040402011018254

DOI

10.1016/j.tet.2011.11.070