Title

Chiral Porphyrin: Piperidine Hybrids for Chiral Guest Recognition

Document Type

Thesis

Degree Name

Master of Science (MS)

Department

Chemistry

Date of Award

Summer 2013

Abstract

The synthesis of several chiral porphyrin host compounds is reported. The hosts were synthesized from the reaction of a porphyrin isocyanate with chiral piperidine and pyrrolidine derivatives. The chiral recognition properties of these porphyrin-based hosts with chiral carboxylate-containing guests is described. A unique aspect of the hosts is their introverted functionality � guest recognition motifs protrude into the interior of the host cavity where they work in tune with the porphyrin metal center for cooperative guest binding. Several hosts display a conformationally-induced organization upon binding to guests similar to that observed in protein chemistry. Binding constants of the chiral porphyrin hosts with guests, which was determined by UV/Vis titration studies, will be reported.

Advisor

Stephen Starnes

Subject Categories

Chemistry | Physical Sciences and Mathematics

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