Quantitative chiral sensing of organic acids by benzimidazole derivatives through H-bond coassembly

Abstract

In this work, we report a highly accurate quantitative ee value detection of chiral acids based on the coassembly between achiral benzimidazole derivatives and chiral acids, wherein the chiral transfer occurred from chiral acids to imidazole probes accompanied by the emergence of Cotton effects. A well-defined linear correlation between g_abs and ee values with a correlation coefficient (R²) up to 0.999 was accomplished in such coassembled systems. Except for the linear g_abs–ee dependence, both positive and negative nonlinear g_abs–ee dependence with high R² (0.999 and 0.998) were also observed. Therefore, the application for the detection of ee values of natural and synthesized chiral acids can be achieved by relying on the fine linear and nonlinear correlations with g_abs. This work provides a simple and generic method to quantitatively determine ee values using novel molecular probes for natural and synthesized chiral acids via a two-component coassembly.