A quality of molecules that causes them to be non-superimposable on their mirror images is known as Chirality. Because of the effects that chirality can have on the chemical and pharmacological properties of molecules, there is an increased interest in developing methods for use in assigning the absolute stereochemistry of chiral molecules. This thesis will detail some of the work we have accomplished using exciton coupled circular dichroism to probe chirality in organic molecules.This dissertation focuses on two parts. The first part introduces the concept of exciton coupled circular dichroism (Chapter I) and introduces the electronically tuned porphyrin tweezer TPFP, which has enhanced sensitivity for chirality sensing (Chapter II). We were able to employ analugues of this tweezer to develop working mnemonics for assigning the absolute stereochemistry of chiral hydroxyl ketones and sulfoxides, two important classes of functional groups commonly encountered as building block in the synthesis of complex molecules.In using tweezers in the study of absolute stereochemistry of molecules, in order to study molecules with only one site of attachment, the molecules are first derivatized with an achiral carrier molecule to provide the second requisite site of attachment. The second part of this dissertation focuses on addressing this group of molecules and the rationale about how we designed and synthesized the MAPOL host molecule that would allow for the assignment of absolute stereochemistry of mono-coordinating molecules, without requiring derivatization with carrier molecules (Chapter III). Lastly, chapter IV will describe the successful application of MAPOL host as a chirality reporter for a number of chiral molecules including mono amines, carboxylic acids and alcohols which would otherwise require derivatization in order to employ conventional methods.
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