Curcuminoid-type difluoroboronate (BF<inf>2</inf>) complexes hold significant importance due to their applications as fluorescent probes. Additionally, they have been employed in detecting β-amyloid deposits linked to Alzheimer's disease. While symmetric curcuminoid-BF<inf>2</inf> complexes are relatively straightforward to synthesize, the production of unsymmetric curcuminoid-BF<inf>2</inf> complexes often results in very low overall yields. In this study, we introduce the use of the mono-ketal derived from 2,4-pentanedione as a molecular scaffold for the synthesis of unsymmetric curcuminoids. These compounds were condensed with 3,4-dimethoxybenzaldehyde or anisaldehyde in basic media, followed by treatment with BF<inf>3</inf>·THF, yielding the corresponding unsymmetric fluorophores with yields varying from good (70% for the anisaldehyde derivative) to excellent (90% for the 3,4-dimethoxy derivative). This method notably contrasts with Pabon's synthesis, in which intermediates are neither isolated nor characterised. Three unsymmetric BF<inf>2</inf>-curcuminoids were successfully obtained, and their optical properties were compared with those of their symmetric BF<inf>2</inf>-curcuminoids analogues. Derivatives 7 and 10 demonstrated promising fluorescence characteristics, showcasing superior optical properties—such as Stokes shift, brightness, and quantum yields—when compared to derivatives 6 and 9. This enhancement is attributed to a significant intramolecular charge transfer (ICT) phenomenon in the former two derivatives, further supported by pronounced changes in the ¹⁹F NMR chemical shifts.