A series of dehydroacetic acid difluoroboron complexes functionalized by a phenyl ring or an electroactive core (tetrathiafulvalene or ferrocene) were synthesized and characterized. The redox properties of these derivatives have been analyzed by cyclic voltammetry and the molecular structures of some of the difluoroboron complexes are presented and discussed. The photophysical properties of selected difluoroboron complexes were determined in solution and in the solid state evidencing an AIEE (Aggregation Induced Enhancement Emission) phenomenon.