Turn on fluorescent probes for selective targeting of aldehydes

Two different classes of fluorescent dyes were prepared as a turn off/on sensor system for aldehydes. Amino derivatives of a boron dipyrromethene (BDP) fluorophore and a xanthene-derived fluorophore (rosamine) were prepared. Model compounds of their product with an aldehyde were prepared using salicylaldehyde. Both amino boron dipyrromethene and rosamine derivatives are almost non-fluorescent in polar and apolar solvent. However, imine formation with salicylaldehyde on each fluorophore increases the fluorescence quantum yield by almost a factor of 10 (from 0.05 to 0.4). These fluorophores are therefore suitable candidates for development of fluorescence-based sensors for aldehydes.