Title

Chiral Pyrrolidine-Porphyrin Hybrids: Prediction of Enantio Preference in Guest Binding A Priori Based on Host Design

Document Type

Thesis

Degree Name

Master of Science (MS)

Department

Chemistry

Date of Award

Fall 2012

Abstract

Here I report the synthesis and chiral recognition properties of several porphyrin hosts with introverted functionality. The hosts are hybrids of tetra phenyl zinc porphyrin and chiral pyrrolidines. The chiral recognition properties of the porphyrin hosts with chiral carboxylate containing guests are described. UV/Vis and 1H-NMR spectroscopic results indicate that urea functionalized hosts shows enantiopreference in binding mandelate tetrabutyl ammonium salt stereoisomers. We can predict which stereoisomer of a guest will preferentially bind to these hosts using a simple binding model.

Advisor

Stephen Starnes

Subject Categories

Chemistry | Physical Sciences and Mathematics

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