Engineering the BASHY Dye Platform toward Architectures with Responsive Fluorescence

Felicidade, F. M. F. Santos, J. F. Arteaga, P. Remón, R. Campos-González, H.-C. Nguyen, F. Nájera, F. Boscá, D. Y. W. Ng, P. M. P. Gois, U. Pischel Chem. Eur. J. 2023,

 A set of nine boronic-acid derived salicylidenehydrazone (BASHY) complexes was synthesized in good to very good chemical yields in a versatile three-component reaction. In extension to previous reports on this dye platform, the focus was put on the electronic modification of the “vertical” positions of the salicylidenehydrazone backbone. This enabled the observation of fluorescence quenching by photoinduced electron transfer (PeT), which can be reverted by the addition of acid in organic solvent (OFF-ON fluorescence switching). The resulting emission is observed in the green-to-orange spectral region (maxima at 520–590 nm). On the contrary, under physiological pH conditions in water the PeT process is inherently decativated, enabling the observation of fluorescence in the red-to-NIR region (maxima at 650–680 nm) with appreciable quantum yields and lifetimes. The latter characteristic supported the application of the dyes in fluorescence lifetime imaging (FLIM) of live A549 cells.