User:Circador/BODIPY

Lead
BODIPY is the technical common name of a chemical compound with formula, whose molecule consists of a boron difluoride group joined to a dipyrromethene group ; specifically, the compound 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene in the IUPAC nomenclature. The common name is an abbreviation for "boron-dipyrromethene". It is a red crystalline solid, stable at ambient temperature, soluble in methanol.

The compound itself was isolated only in 2009, but many derivatives—formally obtained by replacing one or more hydrogen atoms by other functional groups—have been known since 1968, and comprise the important class of BODIPY dyes. These organoboron compounds have attracted much interest as fluorescent dyes and markers in biological research.


 * BODIPY_synth.png

Derivatives
The BODIPY core has a rich derivative chemistry due to the high tolerance for substitutions in the pyrrole and aldehyde (or acyl chloride) starting materials.

Hydrogen atoms at the 2 and 6 positions of the cyclic core can be displaced by halogen atoms using succinimide reagents such as NCS, NBS and NIS - which allows for further post-functionalisation through palladium coupling reactions with boronate esters, tin reagents etc.

The two fluorine atoms on the boron atom can be replaced, during or after synthesis, by other strong nucleophilic reagents, such as lithiated alkyne or aryl species, chlorine, methoxy,  or a divalent "strap". The reaction is catalysed by BBr3 or SnCl4.