A chiral fluorescent probe enables specific recognition of Threoninol

Chiral threoninol derivatives are crucial compounds in the fine chemical, pharmaceutical, and materials industries due to their optical activity and broad applications in organic synthesis and drug development. Although threoninol derivatives share the same molecular formula and atomic connectivity, their different configurations can exhibit significant chemical reactivity and biological activity variations. Thus, selective detection of the individual enantiomers of threoninol remains challenging. In this work, we report the development of a novel chiral fluorescence probe, (S)-5, which features a binaphthol core with dialdehyde and diacrylate moieties as the active recognition sites. This probe selectively interacts with L-Threoninol, resulting in a marked fluorescence enhancement at 540 nm (ef = 3.34), with negligible interference from other substances. The detection limit (LOD) is 3.26 × 10^-8 M. Importantly, (S)-5 itself is nonfluorescent, and its fluorescence is activated upon reaction with L-Threoninol. Additionally, we synthesized the enantiomeric probe (R)-5, which exhibits similar fluorescence enhancement in response to D-Threoninol. To our knowledge, (S)-5 represents the first fluorescent probe specifically designed to detect L-Threoninol. This new probe holds promise as a powerful analytical tool for asymmetric synthesis, chiral resolution, and chiral drug development.