Journal
TETRAHEDRON
Volume 68, Issue 4, Pages 1153-1162Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2011.11.070
Keywords
Polyiodinated BODIPYs; Electrophilic substitution reactions; Nucleophilic substitution reactions; Cross-coupling; Singlet oxygen generation
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Funding
- Spanish MICINN [MAT2007-65778-C02-02, MAT2010-20646-C04-02, 04]
- UCM/BSCH [GR35/10-A]
- Gobierno Vasco [S-PE09UN61]
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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. (C) 2011 Elsevier Ltd. All rights reserved.
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