Title

Electronic Effects on the Chiral Recognition Properties of Chiral Porphyrin Hosts

Document Type

Thesis

Degree Name

Master of Science (MS)

Department

Chemistry

Date of Award

Fall 2016

Abstract

Supramolecular chemistry is the domain of chemistry beyond that of molecules. In supramolecular chemistry, host-guest binding and molecular recognition are well developed fields. Chiral recognition is an emerging branch of research within molecular recognition area. This project mainly focuses on the synthesis of chiral hosts and their studies. Some of the asymmetric side chains are attached to the porphyrins which are positioned directly above the metal center of porphyrins which create a pocket for binding the guests to the metal center of porphyrin. For synthesis of hosts, porphyrin isocyanate was reacted with commercially available chiral amines which have increasing numbers of fluorine atoms attached to them in order to examine the electron-withdrawing electronic effect on anion and amine recognition. Here I report the synthesis of eight hosts of different steric demand and study of their chiral guest recognition. Chiral recognition in the host-guest binding was studied by UV-Visible spectroscopic titrations.

Advisor

Stephen D Starnes

Subject Categories

Chemistry | Physical Sciences and Mathematics

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