Rotamerism-driven large magnitude host–guest binding change in a crown ether derivatized pyridinium-phenolate series

Abstract

Two TICTOID-based pyridinium-phenolates bearing a crown ether macrocycle have been designed for the complexation of a potassium cation. The nucleophilicity of the intraannular phenolate –O⁻ function can be strongly modulated by biaryl twisting. Such a structure/electronic transduction effect gives rise to a host–guest binding change by more than two orders of magnitude.