Multicomponent cycloaddition strategy towards BODIPY triazoles

4,4-Difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY®) is currently one of the most studied fluorescent molecules due to the superior properties. In recent years, our group found and reported several methods of substituting the BODIPY core. The click reaction is a very reliable synthetic method to prepare 1,2,3-triazole heterocycles. Recently, in our group, we have reported several alternative methods to prepare triazoles in a multicomponent approach. Earlier studies in our group of applying the click reaction to BODIPY chemistry were problematic due to (1) the unstability of the acetylene or azide derivatives of BODIPY and (2) the reactivity of copper salts towards BODIPY.A first goal of this project is to adjust the novel organocatalytic triazole forming reactions so that they are compatible with the high sensitivity of the BODIPY nucleus. A second goal will be the synthesis of enamine derivatives of BODIPY, and their use as  acetylene surrogates.Once these two methods are established, a third goal is to apply them to prepare triazole conjugates of BODIPY and molecules of interest, l eading to BODIPY sensors and bichromophoric systems.

Keywords:bodipy triazoles

Disciplines:Medicinal and biomolecular chemistry, Molecular and cell biology, Plant biology, Systems biology, Biophysics