BODIPY

[1] The compound itself was isolated only in 2009,[2][1][3] 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.

[1] In its crystalline solid form, the core BODIPY is almost, but not entirely, planar and symmetrical; except for the two fluorine atoms, that lie on the perpendicular bisecting plane.

[6] Alternatively, dipyrromethenes are prepared by treating a pyrrole with an activated carboxylic acid derivative, usually an acyl chloride.

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.

They strongly absorb UV-radiation and re-emit it in very narrow frequency spreads, with high quantum yields, mostly at wavelengths below 600 nm.

The position of the absorption and emission bands remain almost unchanged in solvents of different polarity as the change of permanent dipole moment upon excitation is small.

[11][12] BODIPY conjugates are widely studied as potential sensors and for labelling biobjects (e.g. cell organelles) [13][14][15][16] by exploiting its highly tunable optoelectronic properties.

BODIPY (unsubstituted)
BODIPY (unsubstituted)
Samples of halogenated BODIPY dyes in ambient lighting and fluorescing under UV
IUPAC atom numbering for substitutions on the BODIPY core. Positions 3 and 5 are also commonly called "α"; 1,2,6,7 are called "β"; and 8 is called "meso". Note that the numbering does not match the numbering on the parent 2,2'-dipyrromethene molecule. [ 7 ]
Molecular structure of 1,3,5,7-tetramethyl-8-phenyl-substituted BODIPY. [ 8 ]