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

Ortiz García, María Josefa; Rodríguez Agarrabeitia, Antonia; Durán Sampedro, Gonzalo; Bañuelos Prieto, Jorge; Arbeloa Lopez, Teresa; Massad, Walter; Montejano, Hernán; García, Norman; Lopez Arbeloa, Iñigo

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

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Official URL

https//doi.org/10.1016/j.tet.2011.11.070

Publication date

2012

Publisher

Elsevier Ltd.

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URI

https://hdl.handle.net/20.500.14352/97790

Citation

Ortiz García, M. J., Rodríguez Agarrabeitia, A., Durán Sampedro, G. et al. «Synthesis and Functionalization of New Polyhalogenated BODIPY Dyes. Study of Their Photophysical Properties and Singlet Oxygen Generation». Tetrahedron, vol. 68, n.o 4, enero de 2012, pp. 1153-62. https://doi.org/10.1016/j.tet.2011.11.070.

Abstract

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.