Executive Summary : | Over the past three decades, molecular recognition has been a significant focus of research, particularly in the creation and use of neutral receptors that can identify neutral molecules and ions. However, designing artificial receptors that can recognize chiral biological anions like amino acids and carboxylic acids remains a challenge due to complex enthalpy and entropy effects and different conformations of the guest and host. This has led to a demand for in-depth studies on the relationship between a receptor's structure and its capacity for effective chiral differentiation. Chiral macrocycles of high symmetry are crucial in science as they can be used as molecular systems for chiral discriminating agents and scaffolds for biomimetic and nanopatterning purposes. The synthesis of macrocycles is often done using thermodynamically controlled imination reactions of predesigned dialdehydes with diamines. A well-tailored macrocyclic or cage receptor can recognize and uptake guest species with stoichiometric discrimination. This research project aims to synthesize various chiral macrocycles with cavities functionalized with Amine, Amide, hydroxy and thiol groups and appended with peripheral trifluoromethyl groups for effective recognition of biological anions. The presence of multiple trifluoro methyl groups along the periphery walls of target macrocycles increases electron deficiency on inner amine, thiol, amide, and hydroxy groups, making them more effective for the recognition of electron-rich biological anions. |