Enantioselective Recognition of Lysine and Phenylalanine Using an Imidazole Salt-Type Fluorescent Probe Based on H(8)-BINOL

An imidazole bromide fluorescent probe (R)-1 based on chiral H(8)-BINOL was synthesized with a high yield; it was found to have good enantioselective recognition of lysine and phenylalanine using fluorescence analysis. When L-lysine was recognized, the enantioselective fluorescence enhancement ratio was 2.7 (ef = I(L) − I(0)/I(D) − I(0), ef = 2.7, 20 eq Lys); as the amount of L-Lys increased, a distinct red shift was observed (the wavelength varied by 55.6 nm, 0–100 eq L-Lys), whereas D-Lys had a minimal red shift. The generation of this red shift phenomenon was probably due to the ICT effect; the probe’s intramolecular charge transfer was affected after (R)-1 bound to L-Lys, and this charge transfer was enhanced, leading to a red shift in fluorescence. In addition to the enantioselective recognition of lysine, phenylalanine was also recognized; the enantioselective fluorescence enhancement ratio was 5.1 (ef = I(L) − I(0)/I(D) − I(0), ef = 5.1, 20 eq Phe).